We expect linear progress (wouldn't that be nice?), but reality delivers something messier: early efforts that feel invisible, momentum that builds slowly beneath the surface, and a valley where doubt creeps in asking "is this even working?"

I've seen this play out in various context:

• The first month at the gym when the scale doesn't budge, but your body is starting the internal transformation for change

• Teams pushing through months of groundwork before breakthrough results

• Learning a language where you feel stuck, right before suddenly understanding conversations

• Products that needed multiple iterations before finding market fit

Here's the hard part: knowing whether you're in a valley worth crossing or a dead-end worth abandoning.

The difference? Valleys have leading indicators of progress. Small signals that you're building toward something, even when the big results aren't visible yet. Dead-ends feel different—no learning, no small wins, no energy. Just depletion.

Smart persistence isn't blind stubbornness. It's having the wisdom to recognize the difference between "not yet" and "not this," the courage to stay the course when the path is right, and the clarity to pivot when it's not.

In product development, it’s knowing when to stay the course and when to pivot. In fitness, it's telling the difference between a plateau and an injury. In careers, it's distinguishing between paying dues and being stuck.

The most rewarding view comes after the steepest climb. And that "overnight success" everyone sees? It was years in the making, most of it spent in the right valleys.

What valley are you navigating right now? And how do you know it's worth the journey?

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His neighbors rushed over, shaking their heads. "What terrible luck!" they exclaimed. "How will you work your fields? This is a disaster!"

The farmer leaned on his fence post, quiet for a moment, and replied with four words: "Maybe so, maybe not."

The following week, the missing horse returned with seven magnificent wild stallions in tow. The neighbors gasped. "What incredible fortune!" they cheered. "You're rich! This is wonderful news!"

The farmer smiled faintly. "Maybe so, maybe not."

Days later, while taming one of the stallions, the farmer's son was thrown violently to the ground, his leg breaking with a loud crack. Again, the neighbors gathered. “How awful! Your poor son! And right in planting season!”

The farmer said it again: “Maybe so, maybe not.”

Soon after, war swept through the land. Soldiers conscripted every able-bodied boy in the village. But when they reached the farmer’s house, they saw the son’s broken leg and moved on.

The neighbors wept as their own sons were taken. Through their tears, they whispered: “How lucky you are.”

And the farmer simply nodded: “Maybe so, maybe not.”

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You may be living your own lost horse moment right now. A door slammed shut. A letdown. A love you thought would last forever has walked away.

Or maybe you’re in your seven horses season. The promotion, the windfall, the applause.

Here’s what the farmer knew: whatever moment you’re in, it’s not the end of your story.

That rejection you think defines you? It may be the redirect that saves you. That heartbreak you think will undo you? It may be clearing the way for the love of your life. That failure you keep replaying? It may become the soil of your greatest triumph.

And yes, even the success you’re savoring—hold it lightly. Not because it will vanish, but because it’s just one chapter in a much bigger book you’re still writing.

The farmer’s wisdom wasn’t detachment. It was perspective. He understood that life’s plot twists are rarely final. They’re turning points.

When you’re in the valley, whisper it to yourself: “This is not where my story ends.”

When you’re on the mountain, breathe it in: there are more peaks ahead.

So today, whatever chapter you’re living, carry his words with you:

Maybe so.
Maybe not.
My story is still unfolding.

Now pick up the pen and write the next page.

Products fall behind customer expectations. Teams spend more time in alignment meetings than shipping. Companies lose track of why they exist. Codebases become "legacy" monuments to technical debt. People skip the gym and avoid difficult conversations, choosing comfort and false harmony over health and clarity.

That's entropy in action. Entropy doesn't announce itself. It's always there in the background, turning everything to shit unless actively fought. Your codebase gets messier unless you prune it. Your processes get heavier unless you simplify them. Your body breaks down unless you rebuild it.

Physics calls this the second law of thermodynamics. It states that entropy always increases in a closed system. It's not just a law of nature; it's the default state of everything.

Fighting entropy is a miserable undertaking. You're debugging code at 6 PM Friday while friends are at happy hour. You're dragging yourself to the gym in a snowstorm. You're having that uncomfortable conversation with a CEO. You're the only one questioning why this process takes six approvals.

Most people don't fight because it hurts. That's why dysfunction is everywhere. The few who do fight—entrepreneurs, athletes, artists, change agents—might be masochists. Or maybe they just can't stand watching things rot.

Here's what makes it worse: in human systems, standing still accelerates decay. In physics, entropy and stasis are opposites. But in organizations, both lead to disorder. When you stop moving forward, you're not maintaining position. You're sliding backward while the world moves on.

In companies, decay disguises itself as prudence. As "rigorous process." As endless analysis that prevents decision-making. Nobody's being malicious. They think they're being careful. But when the incentives reward not failing over succeeding, entropy finds a way in.

That's how Kodak died holding 1,100 digital imaging patents. They were so careful about protecting film profits they missed digital photography. That's how Blockbuster passed on buying Netflix for $50 million. They couldn't risk disrupting their late fee revenue model. They weren't stupid. They were comfortable in their stasis, unable to imagine being unseated.

This is why innovation is the only real antidote to entropy in organizations. But innovation doesn't come from innovation labs or hackathons or strategic offsites.

Real innovation comes from agitation. Someone gets pissed off enough to fix something broken. Jobs thought existing phones were garbage, so he built the iPhone. Two guys couldn't afford rent, had an air mattress, and invented Airbnb. The anger comes first. The breakthrough follows.

Fighting entropy through innovation is exhausting. You'll fail repeatedly before anything works. But here's what I've learned from being part of innovations that both succeeded and failed: entropy wins 100% of the battles that YOU don't fight.

Yes, entropy is the default state. But how much we let it dominate is our choice. I try to fight it daily—in my team, my company, my life. Not because I'll know I’ll win. Entropy always wins eventually.

But not today. Not on my watch.

Tomorrow, the fight starts again.

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Their product is solid and is actually better than their main competitor's. But every time they pitched it, they'd hedge.

"We think it might help with..."
"Some users have said..."
"It's pretty good, we think..."

Meanwhile, their competitor was out there claiming they'd revolutionized the industry. Same features. Worse UI. Double the price. But they said it like they believed it.

Guess who got the Series B.

This happens constantly. Good companies with good products treating their own value like it's something to apologize for. Like confidence is somehow dishonest. Like being excited about what you built makes you a used car salesman.

Look at Jobs introducing the iPhone in 2007. The thing barely worked. AT&T's network couldn't handle it. The battery died in four hours. But Jobs stood up there and told everyone they were about to witness history. And because he believed it, or at least performed belief perfectly, we believed it too.

Compare that to BlackBerry's response. They had better battery life, better email, better security. But their executives kept talking about "enterprise messaging solutions" and "keyboard optimization." They were right about the features. They were also boring as hell. Being right doesn't matter if no one's listening.

Or take Dollar Shave Club. They sold the exact same razors you could buy in bulk from Costco for half the price. But they made a video where the founder walked through a warehouse saying "Our blades are f***ing great." That's it. That's the whole value prop. Confidence and profanity. They sold for a billion dollars.

Even boring products become interesting when someone believes in them:

• Old Spice turned deodorant into masculinity theater

• Geico made insurance funny

• Charmin convinced America to care deeply about toilet paper

• Red Bull created an entire sport just to sell caffeinated sugar water

None of these products are revolutionary. They just had leaders who weren't embarrassed to say "this is great and here's why."

I get why people hesitate. We're trained from childhood that bragging is bad. That modesty is a virtue. That good work speaks for itself.

But work doesn't speak. People do. And if you won't speak for your work, someone else will speak for theirs, louder.

This doesn't mean lying. If your product sucks, fix it. But if you've built something good—something you genuinely believe helps people—and you're standing there shuffling your feet and mumbling about "modest improvements," you're not being humble. You're being negligent.

Your team needs to hear you believe in what they're building. Your investors need to know you'll fight for market share. Your customers need to feel like they're buying something that matters.

Yes, you can overdo it. Theranos overdid it. WeWork overdid it. Hell, OneFootball definitely overdid it. But for every company that dies from too much hype, fifty die from too little. They fade away, apologizing for taking up space, while inferior products with confident founders eat their lunch.

Here's what I've learned after watching hundreds of pitches: The difference between the companies that make it and the ones that don't isn't usually the product. It's whether the founder can look you in the eye and say "This is going to be huge" without flinching.

If you can't do that—if you can't advocate for the thing you've spent years building—why should anyone else care?

Your product might be great. Your team might be brilliant. Your metrics might be perfect. But if you're whispering while everyone else is shouting, you're going to lose.

Not because you were wrong. Because no one heard you.

So get on the damn soapbox. Tell people why your thing matters. Say it like you mean it. Repeat it until you're sick of hearing yourself. Then repeat it some more.

Because shy bats don't hit homers. And modest companies don't change markets.

They just quietly go out of business while their bolder competitors take the swing.

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I've heard this, um, “advice,” doled out for twenty years. Always about someone young getting destroyed by someone powerful. The engineer who got screamed at for missing a deadline. The designer whose work got torn apart in front of the entire team. The PM who got interrupted seventeen times during her first board presentation.

That PM was mine, actually.

The night before her first board meeting, she was in my office at 9pm, clicking through her deck for the twentieth time. She'd nailed it, I thought. Sharp strategy, clean data, and vision that actually made sense.

"You're ready," I told her.

"Yeah, except for him." She meant our President. "He's going to interrupt me three slides in, probably make some comment about how we're overthinking this, then hijack the conversation to talk about whatever he read on TechCrunch this morning."

She said it like she was describing the weather.

"But whatever," she added, forcing a smile. "It'll toughen me up, right?"

I said something useless like "just stick to your narrative" and let her go home to a sleepless night I’m sure.

The next day went exactly as she predicted. Three slides in: "Why are we making this so complicated?" Twenty minutes of him pontificating about some competitor's feature we'd already evaluated and dismissed. Her sitting there, politely nodding, while months of her work got casually shit on.

She handled it perfectly. Professionally. Even salvaged fifteen minutes at the end to cover her key points. Everyone said she did great for her first time.

She quit six months later. Took two of my best PMs with her.

Here's what pisses me off: I let it happen. I sat there watching him derail her presentation, and I did nothing. Told myself she was learning. Building resilience. Developing that thick skin everyone says you need to survive at the top.

But thick skin isn't strength. It's scar tissue. It's what happens when you stop expecting better and start expecting survival.

You know what thick skin actually does? It teaches people to take the hit without questioning why it came. To normalize dysfunction. To mistake endurance for growth. Eventually, you stop feeling the bad stuff. Sure, but you also stop feeling the good stuff. You stop noticing when someone's struggling. You stop caring when culture turns toxic.

I've watched brilliant people turn into corporate zombies this way. They learned to absorb abuse, smile through humiliation, play the game. They got promoted. They got rich. They also got hollow.

What that PM actually needed wasn't thicker skin. She needed someone to interrupt the interruption. To say, "Let her finish." To pull the President aside afterward and tell him he was out of line. She needed courage from her leaders. The active kind that steps forward and says, "this isn't okay."

But courage is harder than telling people to toughen up. It means risking your own comfort. Maybe your job. It means being the person who makes things awkward by calling out bad behavior when everyone else is looking at their shoes.

Most leaders won't do it. Including me, for too many years. We tell people to develop thick skin while the assholes run wild. We prioritize our own survival over our team's dignity. We call it "learning to play the game" or "understanding executive dynamics" or whatever garbage helps us sleep at night.

I regret every time I failed to give someone the backup they deserved.

Meanwhile, talented people keep leaving. Not because they can't take the heat, but because they realize the heat is unnecessary. That other companies exist where you can do great work without developing PTSD. Where challenge comes with support, not humiliation.

That VP who quit? She's a VP of Product at a successful startup now. She messages me sometimes. Never mentions that board meeting, but I think about it every time I see her name.

I think about how I chose the easy path—letting her "toughen up"—instead of the right one. How I confused her surviving with her thriving. How I failed her by not having the courage to protect the courage she walked in with.

These days, when someone tells me a junior person needs thicker skin, I ask a different question: "What does the senior person need to stop doing?"

Because when you tell someone to develop thicker skin, what you're really saying is: "I'm not going to protect you from this. You're on your own."

And that's not leadership. That's cowardice.

Especially when you have the power to stop it but choose not to.

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Then I tried to add user authentication. The AI-generated code had security holes you could drive a truck through. The database schema fell apart when I needed to add a related table. The "polished" UI broke and it wasn’t easy to fix.

In fact, I spent the next three days fixing what took one hour to build.

This is the reality of AI tools that nobody wants to discuss: They're incredible for prototypes and tricky for product development.

What AI Tools Actually Do

I've been using Cursor, Loveable.dev, and ChatGPT daily for months. Here's what I've learned:

1. They make easy things trivial. Building a contact form? Five minutes. Creating a CRUD app? Twenty minutes. These used to take hours.

2. They make medium things dangerous. Complex business logic? The AI will confidently generate code that looks right but fails edge cases you haven't thought of.

3. They make hard things impossible. System architecture? Performance optimization? Security? The AI will hallucinate solutions that sound plausible and fail spectacularly.

The Real Divide

The divide isn't between who’s using AI and who isn’t. It's between those who understand what AI can and can't do, and those who don't.

I watched a junior developer build an AI-generated code that leaked user data. He was curious. He was exploring. He just didn't know enough to recognize bad code when the AI produced it.

I watched a senior engineer use AI to prototype six different approaches in an afternoon, then build the actual solution by hand. She knew exactly where AI helped and where it hindered.

The knowledge still matters. You just apply it differently.

How Roles Are Actually Changing

Engineers: AI helps with boilerplate but can't architect systems. The engineers thriving are those who use AI for the boring parts and focus on the hard parts.

Product Managers: AI can summarize user research but can't make product decisions. PMs who survive will be those who understand AI's outputs are starting points, not answers.

Designers: AI can generate variations but can't understand context. Designers who last will be those who know why something feels wrong, even when the AI insists it's right.

The Uncomfortable Truth

Yes, AI tools are revolutionary. Yes, they're changing how we work. But the breathless evangelism misses crucial points:

• AI amplifies existing skills; it doesn't replace the need for them

• Quality still requires expertise to recognize and achieve

• Most AI-generated work is mediocre (that might be enough for many use cases)

• The real skill is knowing when to use AI and when not to

A More Honest Choice

You don't have to choose between embracing or rejecting AI. The real choice is: Will you understand these tools' limitations and use them wisely? Or will you abdicate judgment to machines that have no concept of quality, correctness, or consequences?

I still use AI tools every day. They've made me more productive. But they've also shown me that expertise matters more than ever.

Because now everyone can generate code. But only those who understand it can tell if it's any good.

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Those who play to win. And those who play not to lose.

At first glance, they look the same. They’re the sharp minds in sleek conference rooms, strategizing, measuring, and forecasting. They speak the same language of KPIs and roadmaps, risk assessments, and growth projections. But beneath the surface, in the marrow, they are not the same. One moves forward with purpose, the other holds back. One is reaching, the other is bracing.

And in that difference—so slight at the start but so vast in the end—lies the whole story of who succeeds and who fades.

Because at the moment of decision, one leaps while the other hesitates. And in that hesitation, a window closes, a possibility vanishes.

Conviction is the great differentiator. It is the thing that turns ideas into movements, ambitions into inevitabilities. It is the force that makes people follow, invest, and believe.

But it must be a particular kind of conviction. Not bravado or delusion. Not the puffed-up certainty of those who mistake noise for wisdom. You know the type. We all do.

Real conviction is something rarer, harder. It is belief, tempered by wisdom. Certainty, softened by humility. The kind of conviction that sees reality with clear eyes and still dares to act.

The Two Mindsets

You can see these mindsets in every arena of human ambition.

The team that plays to win moves with purpose. They are clear-eyed, not reckless. They test and challenge their own assumptions, but when they believe, they believe completely. They do not hedge their bets by only half-committing. They don’t spread resources so thin that no single idea has the weight to take off. They move as if the world needs what they are building, because they know that to get people to believe, they must believe first.

The team that plays not to lose operates differently. They move cautiously, adjusting, and refining, endlessly preparing for what might go wrong. They do not put their full weight into a single conviction because that feels dangerous. What if they are wrong? What if the market moves? What if a competitor does something unexpected? And so they hold back, a little at first, then more over time. They spread themselves across ideas to mitigate risk. They wait for certainty that never comes.

The difference is not just philosophical. It’s practical. It’s operational.

One way creates momentum. The other diffuses it.

One way attracts talent, customers, and capital, because conviction is magnetic. The other makes the world shrug in indifference, because hesitation is forgettable.

Lessons from the Past

Look at the great builders, the ones who changed industries and rewrote expectations.

The Wright brothers believed in flight when the smartest minds of their time said it was impossible. Their belief was not unfounded. It was built on tireless experimentation, on a deep understanding of physics and mechanics. But in the end, it was conviction that made them push forward when others stopped.

Steve Jobs did not build Apple by playing it safe. He operated with an almost unreasonable level of belief. Not in his own genius, but in the idea that people would fall in love with beautiful, intuitive products. He was relentless in that belief, but he was not blind. He listened, observed, adjusted. But he never wavered on the core conviction.

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And look at Sara Blakely, who built Spanx from nothing—no investors, no connections, just a deep belief that women needed something better than what the market was offering. She went all in, pouring every dollar she had into the idea, walking into boardrooms full of men who didn’t understand the problem she was solving. She persisted, refining, iterating, staying open to learning but never compromising her core belief. Today, her brand is ubiquitous, and she rewrote an industry.

Each of these examples contains the same lesson: success comes not just from good ideas, but from the absolute commitment to seeing them through.

The Risk of Playing Not to Lose

Those who play not to lose have their justifications, of course. They will tell you they are being responsible, that they are mitigating risk, that they are avoiding reckless bets. And of course, prudence has its place. But playing not to lose is its own kind of risk.

Hesitation carries a cost. Opportunity is perishable. Markets do not wait for clarity. The biggest risks are often the ones not taken. They’re the moments when an idea, an innovation, a movement was within reach, but leadership faltered, waiting for perfect certainty that never came.

The irony is that playing not to lose often leads to exactly that—losing.

If you are leading, if you are building, if you are deciding—stop and ask yourself:

Am I playing to win, or just playing not to lose?

Hesitation is easy. Caution disguises itself as wisdom. But history doesn’t reward the careful—it rewards the bold. The world moves forward on the backs of those willing to leap.

So leap.

Not blindly. Not foolishly. But with the kind of conviction that is earned.

Believe deeply. See clearly. Adjust when needed.

Then—go all in.

Because in the end, the future does not belong to those who wait. It belongs to those who act with purpose.

Why? Because they confused having necessary ingredients for success with having sufficient ones. And then, paranoid they didn't have enough, they added more of everything until they collapsed under their own weight.

This pattern is everywhere once you start looking for it.

The Necessary vs Sufficient Trap

Necessary means you need it to succeed. Sufficient means if you have it, you will succeed.

A ticket is necessary to attend a concert. But it's not sufficient. You also need the band to show up and the sound system to work. Together, those conditions are sufficient for a concert experience.

Simple concept. Yet companies screw this up constantly.

They identify what's necessary (funding, talent, customers) and assume more of those things will guarantee success. So they raise too much money, hire too many people, chase too many customers. They turn a lean operation into a bloated mess.

What This Actually Looks Like

I've seen this play out three ways:

The Funding Trap

Company raises $5M seed round. Does well. Thinks "if $5M got us this far, imagine what $50M could do!" Raises huge Series B.

Suddenly everything changes. Discipline disappears because runway seems infinite. They hire 100 people instead of 10. Build features nobody asked for. Open offices in three cities. Burn rate explodes.

The $5M was sufficient. The $50M was overkill. The extra money didn't accelerate success; it accelerated failure.

The Process Trap

Growing company has quality issues. Adds review process. Still has issues. Adds approval process. Still has issues. Adds committee oversight.

Now launching anything takes three months instead of three weeks. The best people quit because they can't get anything done. Quality doesn't improve because the problem was never process. It was unclear ownership.

One good process was sufficient. Five processes became organizational sludge.

The Feature Trap

Product has three features customers love. PM thinks "if three features got us this far, imagine what thirty could do!"

Two years later: bloated product nobody understands, confused customers, and competitors eating your lunch with simpler alternatives.

The three features were sufficient. The other 27 were expensive distractions.

The Marketplace Example That Actually Matters

I worked on a ticketing marketplace that learned this lesson the hard way. We knew trust was necessary (buyers need to know tickets are real). We knew inventory was necessary (need tickets to sell).

But instead of stopping at sufficient, we kept adding:

• Price prediction algorithms

• Seat view photos from 12 angles

• Social features to see where friends were sitting

• Personalization engine for recommendations

None of it moved the needle. You know what did? Making checkout take 30 seconds instead of 3 minutes. That was sufficient.

How to Find Your "Sufficient"

Ask two questions:

1. "What else needs to be true for this to work?" Keep asking until you have the minimum complete system.

2. "If we added nothing else, would this succeed?" If yes, stop adding.

Most companies never ask the second question. They're so paranoid about not having enough that they add backup plans to their backup plans. They hire two people for every role just in case. They build features for edge cases that might happen someday.

The Uncomfortable Truth

Knowing when you have enough requires confidence most organizations lack. It's easier to add than subtract. Easier to hire than fire. Easier to say yes than no.

But every addition has a cost. Not just money, but complexity, speed, focus. The cost compounds until what was once a simple, sufficient system becomes an unwieldy mess that can't get out of its own way.

The startup I mentioned at the beginning? They had sufficient conditions for success at $10M raised and 25 employees. The extra $40M and 75 people didn't add capability. They added complexity that killed the company.

Your job isn't to have everything. It's to have enough of the right things.

Most of the time, enough is all you need.

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Emma lasted exactly three weeks at her new job before VisionCore called her back.

"Consultant," Vince had said on the phone, his voice missing its usual swagger. "Not employee. We need someone who understands what went wrong with SyncGo."

"You fired me for understanding what went wrong with SyncGo."

"That was... a misunderstanding."

Emma quoted a day rate that should have ended the conversation. Vince agreed immediately, which told her things were worse than she'd imagined.

She walked back into VisionCore's offices on a Monday morning, carrying nothing but a laptop and the knowledge that she could leave whenever she wanted. The contract was week-to-week. The moment Vince reverted to his old patterns, she'd walk.

The Pitch

"AI-powered sunglasses," Vince announced at the kickoff meeting.

Emma started packing her laptop.

"Wait," Vince said quickly. "This time is different. We're doing validation first. Real validation. That's why you're here."

Emma stopped packing but didn't unpack. "How long do I have?"

"Four weeks."

She resumed packing.

"How long do you need?" Vince asked, desperation creeping into his voice.

"Minimum eight weeks for discovery. Probably twelve to be sure."

"You have six."

Emma looked around the room. Rick Chen was still there, looking exhausted. Sarah Kim had been promoted to Lead Designer, though her enthusiasm had been replaced with wariness. A few new faces, probably hired to replace those who'd fled after SyncGo.

"Six weeks of real research," Emma said. "No building anything until I present findings. No prototypes, no engineering sprints, nothing."

"Fine."

"I want that in writing."

Vince's jaw tightened, but he nodded.

The Research

Emma brought in two junior researchers from her network, people she trusted to ask real questions and document real answers. They ran the discovery like anthropologists studying an undiscovered tribe.

Week one: Airport lounges and train stations, talking to travelers about their pain points.

Week two: Tech stores and coffee shops, understanding how people actually used wearables.

Week three: Focus groups with people who'd bought and returned smart glasses from other companies.

The patterns emerged quickly:

• Nobody wanted another device to manage

• Sunglasses were inherently limited by weather and time of day

• Sunglasses were deeply personal and everyone already had a pair from their favorite brand

• The price point ($300) competed with established products that did more

• Translation apps on phones worked fine for most situations

"We're solving a problem that doesn't exist," Emma told her researchers.

"What do we tell Vince?" one asked.

"The truth. With data."

The Presentation

Six weeks later, Emma presented to the leadership team. She'd prepared forty slides but knew she'd only get through ten before someone interrupted.

She made it to slide three.

"You're telling me nobody wants smart sunglasses?" Vince interrupted.

"I'm telling you nobody wants these smart sunglasses at this price point for these use cases."

"But Google Glass—"

"Failed."

"Magic Leap—"

"Pivoted to enterprise."

"Apple is working on—"

"Something that probably isn't sunglasses."

Rick Chen spoke up. "My team has been researching the technical requirements. Even if we wanted to build this, the battery life would be two hours max. Nobody's going to charge their sunglasses every two hours."

Sarah added, "The interface design is nearly impossible. You can't put a meaningful display on sunglass lenses without making them look like a heads-up display from a fighter jet."

Vince stood up, pacing. "So you're all telling me we should just give up?"

"I'm telling you," Emma said calmly, "that we should build something people actually want."

The Pivot

"Fine," Vince said after a long silence. "What do people want?"

Emma clicked to slide twenty-seven, which she'd titled 'What We Actually Learned.'

"Translation technology that works in noisy environments. Every traveler we interviewed wanted this. But not in sunglasses. They wanted it in their existing earbuds."

"That's not innovative," Vince protested.

"It's a $2 billion market that's actually growing."

"But we announced sunglasses—"

"To who? Nobody outside this room knows what we're building."

Kathryn, the COO who'd stayed silent since SyncGo, finally spoke. "How long would the earbud software take to develop?"

Rick pulled up his laptop. "If we're just building software for existing hardware? Three months. Maybe four for a really polished version."

"And the market?" Kathryn asked Emma.

"Every major earbud manufacturer is looking for differentiating software. We could license to all of them."

Vince slumped in his chair. "Software licensing. That's not the kind of company I wanted to build."

"No," Emma said. "You wanted to build the next Apple. But Apple spent decades making computers work better before they revolutionized phones."

The Decision

The room went quiet. Emma watched Vince wrestle with his ego, his vision, his need to be seen as a visionary.

"I need to think about it," he finally said.

Emma shrugged. "My contract ends Friday. Let me know by then."

She left the meeting and went to the coffee shop across the street, where Sarah found her an hour later.

"He's still in there, drawing on the whiteboard," Sarah reported.

"Drawing what?"

"Sunglasses with increasingly ridiculous features. I saw one that included a laser pointer."

Emma laughed. "At least that solves a real problem."

The Ultimatum

Thursday afternoon, Vince called Emma into his office. The whiteboard was covered with drawings, equations, and what looked like poetry about innovation.

"I can't do it," he said. "I can't be the CEO who makes translation software for other people's hardware."

"Okay," Emma said, already mentally drafting her final invoice.

"But," Vince continued, "what if we made our own earbuds? Premium ones. With our translation software as the killer feature?"

Emma considered this. "That's still hardware. Expensive to develop, expensive to manufacture."

"But it's ours. Our product, our brand, our innovation."

"How long do I have to validate this?"

"You don't," Vince said. "Your contract ends tomorrow."

Emma studied him. "You're going to build it anyway."

"I'm going to build something. With or without validation."

"Then you'll fail. Again."

Vince smiled, but it was sad. "Probably. But at least I'll fail building something I believe in."

The Exit

Emma packed up her temporary desk, which had never really been unpacked. Rick walked her out.

"You tried," he said.

"I got paid to try. You have to stay and watch it fail."

"Already interviewing elsewhere. Sarah too."

They stood in the parking lot, looking back at the building where so many bad decisions were about to be made.

"What's your prediction?" Rick asked.

"Six months until launch, another three until failure. They'll burn through about fifteen million."

"I say four months to launch. Vince is desperate now."

Emma's phone buzzed. A text from her actual boss at her actual job: "Client loved your recommendations. They want you to lead the implementation."

"I have to go build something boring that customers actually want," Emma told Rick.

"Living the dream."

"Unironically, yes."

Epilogue: Eight Months Later

Emma was reviewing user feedback for her company's latest feature when Sarah texted her a link.

"VisionCore Announces Pivot to Enterprise Software After Smart Earbuds Fail to Gain Traction"

The article included a quote from Vince: "We learned valuable lessons about the importance of market validation and customer-centric design."

Emma texted back: "How many times can someone learn the same lesson?"

"Until they run out of money," Sarah replied. "So probably once more."

Emma turned back to her spreadsheet of customer feedback. Every row represented someone who actually used their product, had actual problems, and paid actual money for solutions.

It wasn't revolutionary. But it was real.

Her phone rang. Unknown number, but she recognized the area code. VisionCore's neighborhood.

She let it go to voicemail.

Some lessons, she'd learned, were only valuable if you were willing to learn them.

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So I asked Operator to find me the “best deal” on a Honda Accord near me.(see video).

Watching how it approached the task (e.g, searching on Bing, clicking the first result, not knowing how to handle “best deal”, etc.) was fascinating. While it couldn’t fully complete my request, I was impressed by the potential this represents.

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This is just the beginning and it’s pretty awesome.

As Operator integrates directly with APIs and as brands improve their use of structured web data, its ability to handle more complex tasks, like finding the “best deal”, will evolve significantly.

It’s an exciting time as AI Agents start to give us back time in both our personal and professional lives. I’m especially thrilled how we — at CarGurus — are helping car shoppers and dealers reclaim valuable time through AI and data innovation.

2025 is already off to a great start! 🚀

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This story might feel uncomfortably familiar. Reader discretion is advised.

Emma Caldwell arrived at VisionCore on a rainy Monday in October, carrying a banker's box of desk plants and the weight of three failed startups. At forty-two, she'd learned that Director of Product roles came in two flavors: fixing something broken or building something new. She'd been hired for the former.

Two months later, she discovered she'd been wrong.

"We're going to eat FlashLoop's lunch," Vince Moretti announced, clicking to a slide showing a hockey stick graph. The CEO had the kind of energy that made you want to believe impossible things. "Forty percent month-over-month growth. Ten million ARR. All Gen Z users."

Emma sat in the back row, watching her new colleagues lean forward. She recognized the hunger in their eyes. She'd felt it herself once, before she'd learned what that hunger cost.

"I'm calling it SyncGo," Vince continued. "We launch in four months."

Emma's coffee turned cold in her hands. Four months. For a product that didn't exist yet, for a market they didn't understand, for users who weren't theirs.

When Vince asked for questions, Emma waited. Let someone else be the skeptic. But the room stayed silent, everyone nodding like dashboard bobbleheads.

She raised her hand. "Who's our target user?"

"Gen Z," Vince said, already moving to the next slide.

"But specifically—"

"Emma." Vince's smile had edges. "I hired you to ship products, not to slow us down. FlashLoop proved the market. We just need to execute better."

The Team

Rick Chen, VP of Engineering, found Emma in the kitchen after the meeting. "You're not wrong," he said quietly, pouring coffee that looked like motor oil. "But Vince has already promised the board. We're building this thing."

"You've been here five years," Emma said. "How often does this happen?"

Rick's laugh was bitter. "Remember TurboChat? No? Exactly. Twelve million dollars. Dead in six months."

"And you didn't push back?"

"I have two kids in college and a mortgage in Palo Alto." Rick dumped sugar into his coffee. "I push back by making sure my resume is updated."

Sarah Kim from Design joined them, her iPad covered in sketches. Twenty-six years old, all ambition and no scar tissue yet. "I'm actually excited about SyncGo. My little brother is Gen Z. I know exactly what they want."

Emma wanted to warn her. Instead, she asked, "What does your brother think of FlashLoop?"

Sarah's enthusiasm dimmed slightly. "I haven't actually asked him yet."

The Build

Emma tried. She scheduled user interviews that got cancelled for "urgent sprint planning." She created personas that got ignored for being "too academic." She ran a competitive analysis that Vince dismissed as "looking backward instead of forward."

Meanwhile, the machine churned. Rick's team built infrastructure for features nobody had defined. Sarah's designers created interfaces for problems nobody had articulated. Marketing prepared campaigns for users nobody had met.

In week six, Emma made one last attempt. She'd spent her weekend at a college campus, talking to actual Gen Z users. She'd recorded their interviews, documented their needs, mapped their current solutions.

"None of them have heard of us," she told the leadership team. "And when I explained what SyncGo would do, they asked why they wouldn't just keep using FlashLoop."

Vince's face darkened. "You went behind my back to validate my vision?"

"I went to validate our product."

"My product," Vince corrected. "And it's already validated. FlashLoop validated it. Now stop questioning and start shipping."

The Launch

Four months later, SyncGo went live with a Super Bowl commercial Vince had insisted on. Two million dollars for thirty seconds of hype.

Emma watched the metrics dashboard from her apartment, having called in sick. She couldn't bear to be in the office for the celebration that would turn into a wake.

Hour one: 500 signups. The projection had been 10,000. Hour four: 80% of users abandoned onboarding. Hour twelve: The first TechCrunch article. "VisionCore's Super Bowl Fumble."

Her phone buzzed. Sarah: "This is a disaster. Nobody understands what it does."

Then Rick: "Emergency meeting tomorrow. Vince wants answers."

The Reckoning

The conference room felt like a courtroom. Vince stood at the whiteboard, drawing circles and arrows like he could diagram his way out of failure.

"We moved too slowly," he said. "FlashLoop had first-mover advantage."

"We moved too fast," Emma countered. "We never figured out what we were building."

"You never believed in the vision," Vince shot back. "That negativity infected the team."

Sarah spoke up, surprising everyone. "I believed. I was excited. But Emma was right. We never talked to actual users. My brother laughed when he saw our commercial. Said it looked like adults trying to be cool."

Rick added, "The technical execution was flawless. We built exactly what we were asked to build. The problem is what we were asked to build."

Vince's face went red. "So it's my fault?"

The room went silent. Emma realized everyone was waiting for her to answer. To be the sacrifice that would let them all move forward.

"It's not about fault," she said finally. "It's about learning. We copied a solution without understanding the problem. We valued speed over insight. We mistook motion for progress."

"You're fired," Vince said quietly.

"I know," Emma replied.

The Aftermath

Emma packed her desk plants while Sarah hovered nearby. "I'm sorry," the younger woman said. "You tried to warn us."

"I tried to warn myself too," Emma said, wrapping a succulent in newspaper. "But I still took the job. I saw the red flags and convinced myself I could change the culture."

"Will you find another product role?"

Emma looked at her half-packed box. "Probably. And it'll probably end the same way. Because most companies don't want product managers. They want feature factories with human faces."

Rick appeared with a bottle of scotch. "For the road," he said. "And for what it's worth, my resume is already out there. Sarah's too."

"Vince will survive this," Emma said. "He'll blame market conditions or execution speed or me. The board will give him another chance."

"And SyncGo?"

"They'll pivot it into something else. Rebrand it. Then quietly shut it down in six months when no one's paying attention."

Emma picked up her box. Three months at VisionCore. Not her shortest tenure, but close.

As she waited for the elevator, she heard Vince's voice from the conference room: "We need to move faster on the next product. I'm thinking AI. Everyone's doing AI."

Emma stepped into the elevator. Some lessons were only learned by those willing to learn them.

The doors closed on VisionCore. By the time they found their next Emma Caldwell, they'd have burned through another ten million.

She'd read about it in TechCrunch, probably. Another story of a company that confused confidence with competence, speed with strategy, copying with creating.

Her phone buzzed. A recruiter. "Director of Product role at a fast-moving startup. They need someone to help them compete with..."

Emma deleted the message and drove home.

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Once upon a venture daring,
Came a voice, both bold and blaring,
“Why waste time with careful pairing?
Build it now! Just build, explore!”
Yet in shadows, soft and creeping,
Echoed lessons, darkly seeping,
Warnings from past efforts sleeping,
Whispering, “Validate once more.”

“Boldness!” cried the leader, grinning,
“Fearless builders for the winning!
Don’t get stuck with careful spinning — 
Just build the thing! That’s the lore!”
Yet beneath this booming thunder,
Lurked the echoes of past blunders,
Of several ventures torn asunder,
Ruins scattered on the shore.

“We need no plans, no exploration!
Questions breed only hesitation!
Leap, and build the grand creation!
Bravery’s what we adore!”
But while he preached this path unbending,
History’s lesson, still unending,
Showed the cost of blindly spending,
Dreams turned ashes, hopes no more.

Now the men sit, softly musing,
Knowing that to act, not proving,
Is a perilous path of choosing,
Risking chaos at its core.
For they’ve learned through pain and burning,
That the wheel is always turning,
Thoughtful action keeps the yearning
Focused sharp on what’s in store.

So they nod at the leader’s rally,
Join the march down hubris’ alley,
Yet in corners, plans they tally,
Testing truths to build once more.
For the lesson, stark, resounding,
Speaks of ventures once astounding,
Built on sand, no solid grounding,
Lost to hubris’ endless roar.

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If you're running a team, a department, or a company, you know the feeling. You're steering the ship, but most of the time you're doing it alone in your cabin while everyone else is on deck.

This isolation isn't just about making tough decisions in private. It's about carrying responsibilities that fundamentally separate you from everyone else in the organization.

Real leadership means having hard conversations nobody wants to have. Making calls that piss people off. Putting the company's survival over being liked. Dealing with organizational politics. Accepting you'll screw up regularly. And standing firm when people think you're wrong.

The Weight of Decision-Making

Every leadership decision has a lonely moment before it. The moment where you realize the choice is yours alone and everyone's waiting.

Strategic pivots. Budget cuts. Personnel changes. Each one affects the entire company and the people in it. Sure, you can get input, run surveys, build consensus. But at some point, someone has to make the call. That someone is you.

The solitude comes from knowing that if it goes wrong, it's on you. Not the team. Not the board. You.

The Business Comes First

Your primary job is keeping the organization healthy and viable. This means making choices that won't win you any popularity contests.

Cutting a beloved but unprofitable product. Saying no to raises when cash is tight. Killing someone's pet project because it doesn't align with strategy.

These decisions create distance. People take them personally even when they're not personal. You become the person who said no to something they cared about. That gap between what's necessary and what's popular. That's where leaders live.

Navigating Politics

Every organization has politics, whether they admit it or not. As a leader, you're constantly advocating for what's right against competing interests and agendas.

Standing up for an unpopular but necessary change. Challenging comfortable assumptions. Pushing back against the loudest voices in the room.

This isn't noble leadership. Tt's just the job. But it's isolating when you're the only one willing to say the uncomfortable thing.

Learning From Mistakes

Leaders make mistakes. Publicly. Repeatedly.

Bad hires. Failed initiatives. Wrong strategic calls. Each mistake is a lesson, but it's a lesson you have to process alone. You can't blame the team or make excuses. You own it, learn from it, and hopefully don't repeat it.

The reflection required after each failure is deeply personal. You're asking yourself: What did I miss? Why did I think that would work? How do I prevent this next time?

Facing Detractors

If you lead long enough, you'll have critics. People who disagree with your decisions. People who wanted your job. People who think they could do it better.

The Charles Mackay poem puts it well:

YOU have no enemies, you say?
Alas! my friend, the boast is poor;
He who has mingled in the fray Of duty,
that the brave endure,
Must have made foes!

Standing firm when people are actively rooting for you to fail tests your conviction. But if you're making real decisions and driving real change, opposition is inevitable.

Navigating the Solitude

Some things that actually help:

• Find peers outside your organization. Other leaders who understand the weight you're carrying. They don't need to be mentors, just people who get it.

• Create clear communication channels. The more transparent you can be about your reasoning, the less mysterious and isolated your decisions seem.

• Build in reflection time. Don't just jump from decision to decision. Process what happened, what you learned, what you'd do differently.

• Accept the distance. You can be human and approachable without pretending you're everyone's friend. The role creates separation. Fighting it makes it worse.

• Keep learning. The job keeps changing. If you're not growing, you're just getting more isolated in outdated thinking.

Leadership solitude isn't a bug. It's a feature. The role requires making decisions others can't or won't make. That's inherently isolating.

But here's the thing: You chose this. At some point, you decided the impact was worth the isolation. The ability to drive change was worth the criticism. The responsibility was worth the weight.

Some days that trade-off feels worth it. Other days, less so.

That's leadership.

This is where rubrics come in.

Unlike vague value statements, rubrics offer a clear choice in behavior, making them remarkably better tools for shaping an organization’s culture.

Why Value Statements Fall Short

Value statements like “Integrity,” “Innovation,” or “Customer-Centricity” are noble but often lack specificity, and sometimes trigger a cringe or an eye-roll.

Value statements are broad strokes that paint a picture of an organization’s ethos but don’t necessarily guide day-to-day decision-making.

For instance, what does “Innovation” mean when you’re faced with a high-stakes project deadline? Should you take a risk on a new approach, or stick with tried-and-true methods to ensure timely delivery?

What action is expected of you in the context of this culture?

The Power of Rubrics

Rubrics, on the other hand, offer a powerful alternative to value statements that guide behavior by presenting a clear choice.

Take, for example, the statement “Courage over Comfort.” This encourages employees to step out of their comfort zones and take calculated risks, even when it’s easier to maintain the status quo.

Example: Jo, a Senior Data Analyst at a struggling e-commerce startup, decides to bring up the issue of outdated data analytics tools in a team meeting despite knowing it might not be well-received.

Her courage to speak up becomes a turning point, leading to more efficient decision-making that helps stabilize the company. It would have been easier to stay silent and think, “We have a bigger fish to fry,” but she didn’t.

Why? Because the rubric used in her culture expects her to be courageous when it’s inconvenient.

The Versatility of Rubrics

Rubrics can be tailored to address various aspects of organizational behavior and decision-making.

Consider the rubric “Action over Deliberation,” which emphasizes the importance of making timely decisions and urging bias for action.

Example: Jo observes that the sales team is consistently missing targets. Instead of waiting for another team meeting, she immediately analyzes the sales data and creates a dashboard that transparently shows real-time sales performance, thereby increasing accountability within the sales team.

Rubrics in Action

Rubrics offer a holistic framework for decision-making. For instance, a well-rounded rubric might include:

#1 Courage over Comfort

This choice encourages individuals to take calculated risks and step out of their comfort zones. It’s about making the tough but right decisions for the organization, even when it’s easier to maintain the status quo. It’s about speaking up, giving feedback, and doing the right thing when the outcome is uncertain. This is what “integrity” is all about.

#2 Action over Deliberation

This choice emphasizes the importance of making timely decisions and taking immediate action. While it’s crucial to think things through, excessive deliberation can lead to paralysis and missed opportunities. Some companies call this “bias for action,” others call it “having a sense of urgency.” Less talk, more action, is what it all boils down to.

#3 Progress over Perfection

This choice urges making continuous progress over waiting for perfect conditions or solutions. It encourages team members to do the best they can with the resources they have, learning and iterating along the way. Some companies might call this “agile” or “nimble” in their value statements.

#4 Customer over Operational Ease

This choice prioritizes customer satisfaction and experience over internal operational convenience. It serves as a reminder that the ultimate goal is to serve the customer, even if it requires extra effort or resources. There’s a common tug-of-war in product organization between the idealism of customer centricity and making money.

A business has to make money. Otherwise, it’s not a business. What this statement calls out is that we need to focus on customers AND make money, which oftentimes involves operational complexity, hence the statement.

#5 Team over Solo Heroics

This choice emphasizes the importance of teamwork and collaboration over individual efforts, no matter how heroic. It encourages a culture where team success is celebrated above individual achievements.

The rubric above, with its five statements, can serve as a guide for behavior and decision-making in your company, encapsulating a culture that values courage, action, progress, customer focus, and teamwork.

Parting Thoughts

While company values provide a broad outline of an organization’s ideals, rubrics offer the specificity needed for practical application. They present employees with clear choices, making it easier to align individual actions with organizational goals.

In a world where every decision can have far-reaching implications, the clarity provided by rubrics is invaluable. So, the next time you’re looking to shape or reshape your company’s culture, consider opting for rubrics over traditional value statements. The impact on your organization could be remarkably better.

If you currently use a rubric in your company, please share it here. Would love to learn from your experience.

That’s 80% of the world’s workforce checked out, costing the global economy $9 trillion.

According to the Pareto Principle, this all makes sense — 80% of the impact is made by 20% of the workforce.

But as the world becomes increasingly stressful, the effective 20% is now at risk. This is why companies are listing talent retention as their most important operational priority, ahead of revenue growth.

Think about it. We’re all dealing with a lot right now — war, social reckoning, economic woes, climate collapse, and more. At work, companies are battening down the hatches, trying to do more with less, and particularly with fewer people. Everyone’s on the lookout for the other shoe to drop, exacerbating an already stressed-out psyche.

It’s definitely Wartime for many tech companies right now. The question is: Can Wartime CEOs and executives keep their top talent — the 20% — engaged and motivated?

It depends. Here’s what I’ve seen leaders do at companies that managed to retain top talent during times of crisis.

#1 Dismiss Low Performers

Putting up with low performers is a leadership failure in “Peacetime”. In times of crisis, it’s the nail in any company’s coffin. The example below highlights how tolerating underperformance impacts top talent:

Meet Nina

Nina is a Senior Data Analyst at ShopEase — a once fast-growing but now struggling e-commerce startup. Nina’s been a beacon of efficiency her entire tenure at the company. Her data-informed insights have been crucial in optimizing the supply chain, reducing costs, and improving operational efficiency — key factors in the company’s fight for survival right now.

But as ShopEase enters a critical phase in its operations, desperately needing to secure more revenue to stay afloat, Nina observes that the sales team, led by Alex, is consistently missing their targets. Despite the company being on the brink of collapse, Alex faces no repercussions from Olivia, the COO, who seems to tolerate the underperformance.

During a high-stakes project aimed at optimizing warehouse logistics to cut costs further, Nina finds that the sales team’s failure to meet targets is directly affecting the already limited operations budget. When she raises the issue in an emergency team meeting, Olivia’s response is dismissive: “We’re all under pressure; let’s focus on what we can control. Sales will catch up.”

Feeling frustrated and alarmed, Nina decides to discuss the issue with her direct manager, Ethan: “The lack of accountability in sales is not just affecting this critical project but also jeopardizing the company’s survival. It’s as if we’re tolerating failure at the worst possible time.”

Ethan’s response is sympathetic but ultimately unhelpful: “I understand, Nina. Olivia is trying to keep the team together during this crisis. Let’s just get through this project, and we’ll sort out the performance issues later.”

Despite Ethan’s assurances, “later” never comes. The project is completed, but only due to the Herculean effort from Nina and a few other top performers. The sales team continues to miss targets, and the company’s financial situation worsens.

Nina finds herself increasingly disengaged and starts to consider other career opportunities, even in the midst of a crisis. She’s not alone; other top performers who have been carrying the weight of the team begin to feel the same way.

She’s now seriously contemplating her options: Should she look for a new job where her skills will be better utilized, or should she stay and continue to be part of a sinking ship?

The culture of tolerating underperformance in sales has not only affected her but is also exacerbating the existential crisis facing ShopEase. She begins to question the leadership and wonders how this will impact the startup’s already slim chances of survival.

Advice for Leaders

When it’s all hands on deck, accountability is critical. Your people are watching. If you put up with mediocrity on your team when you’re in survival mode, you’re sending a signal to the best on your team that you don’t have what it takes to right the ship.

High performers have options and are light on their feet, especially when the going gets tough, and their efforts are dragged down by incompetent colleagues.

It’s never too late to course correct. Act now.

#2 Mind Your Culture

Your best people want to operate in an environment that has the following ingredients:

• Accountability (see #1)

• Decisiveness

• Autonomy

• Recognition

• Self-awareness

• Humility

Taking care of culture is very much like taking care of our bodies, especially under duress.

Strive for exceptional, and you’ll end up with great. Strive for great, and you’ll end up with good. Strive for good, and you’ll end up with mediocre. Tolerate mediocre, and you’ll end up with entropy.

Once you hit entropy, the inertia to course correct is so high it’s almost impossible to overcome.

Your best people won’t survive in a state of entropy. They will leave.

Meet Steven

Steven is a Senior Product Manager at the fintech startup, NetWorth. Steven is known for his knack for innovation. He’s the brains behind several features that have been critical for user engagement and revenue. He’s one of the company’s top performers.

But as NetWorth grapples with a financial crisis and an uncertain future, Steven starts to feel the weight of the company’s dysfunctional culture.

Carl, the CEO, is a micromanager who’s paralyzed by indecision. He scrutinizes every detail of Steven’s projects but avoids making any concrete decisions. This leaves Steven in a perpetual state of limbo, unable to move forward with initiatives that could be game-changers for the struggling company.

Adding to the frustration, Carl never acknowledges Steven’s efforts. Instead, he nitpicks minor issues, diverting focus from the larger objectives. When Steven turns to Lisa, his VP of Product, for support, she acknowledges the problem but offers no real solutions.

“Carl’s under a lot of stress,” she says. “Let’s just keep our heads down and get through this project.”

But “getting through” becomes increasingly difficult. The culture of micromanagement and indecision is suffocating, and it’s clear that the leadership lacks both self-awareness and the ability to reflect on what’s really going on with the people on the ground.

As the company’s financial situation worsens, so does the work environment.

Steven starts to disengage. He’s no longer excited about his projects and begins to question whether his skills would be better utilized elsewhere. He notices he’s not alone; other high-performing colleagues are also showing signs of disengagement.

Finally, Steven reaches a tipping point. He updates his resume and starts exploring new opportunities. It’s a difficult decision, but Steven can’t help but think that staying would mean being part of a sinking ship with a captain who refuses to change course.

The toxic culture at NetWorth has far-reaching consequences. Not only has it disengaged one of its top performers, but it’s also accelerating the company’s downward spiral. Steven’s departure becomes a symbol of the company’s broader issues — a lack of leadership self-awareness, a culture that stifles excellence, and a failure to act during an existential crisis.

Advice for Leaders

Culture matters, especially in times of crisis. If you think it’s the least of your worries, you’re mistaken. It’s the soft tissue that makes the hard things needed to survive in business work. Mind your culture to keep your best people engaged and motivated.

Parting Thoughts

The stakes have never been higher for leaders in the tech industry.

The global workforce is largely disengaged, and the invaluable few that drive most of the impact are under unprecedented stress with challenges ranging from geopolitical instability to internal organizational pressures.

Yet, the companies that navigate these turbulent waters successfully have a common thread: decisive leadership that prioritizes talent retention.

This is not the time for indecisiveness or neglecting your company culture. Effective leaders act swiftly to part ways with low performers and double down on cultivating an environment that not only retains but also nurtures the best in their workforce.

It’s Wartime; your ability to maintain a motivated and engaged team could very well be your competitive edge. Ignore it at your peril.

In his book, A CEO Only Does Three Things, Trey Taylor asserts that a CEO’s job is to take care of people, culture, and numbers, in that order. Everything else should be delegated. But to do the job well, you need to master self-awareness.

“Self-awareness is the foundation of self-management and decision making.” — Trey Taylor

Assuming the CEO does a good job hiring and retaining the right talent, her next challenge is cultivating a culture of accountability, empowerment, and innovation.

But culture isn’t about free lunches and value statements. Culture is about behavior, and it all starts with the behavior of the CEO. You can’t recognize and improve behavior if you’re not self-reflective and self-aware.

You won’t have a culture of accountability if you’re unaccountable yourself. You won’t have a culture of empowerment if you micromanage your team and strip them of their autonomy. You won’t have a culture of innovation when you stifle it with interference and indecision.

You won’t have a team if you’re unwilling to recognize and change your behavior.

The hallmark of a culture of accountability, empowerment, and innovation is autonomy. The great talents you’ve hired require autonomy to give you their best work.

"I'd rather interview 50 people and not hire anyone than hire the wrong person." — Jeff Bezos

To achieve autonomy, you need to be clear on how decisions are made, who can make them, and under what conditions. It all comes down to the standard you set for managing decision-making for yourself and your team. Accountability, empowerment, innovation, and in turn, autonomy, all stem from that.

Let’s take a closer look.

Strategic Decisions vs. Operational Decisions

Great CEOs are crystal clear on what decisions stay with them and what decisions don’t. They know the company is counting on them to make strategic, consequential, high-risk decisions and be accountable for them.

Great CEOs have done the hard work ensuring they have the right people in the boat, which frees them to focus on the most critical, high-risk aspects of the business. They also know they can delegate all other aspects of the business to the senior executives and their teams.

"The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint enough to keep from meddling with them while they do it.” — Theodore Roosevelt.

There are two types of decisions companies make every day: strategic decisions and operational decisions.

Strategic Decisions

Strategic decisions are long-term choices that have a significant impact on the direction and success of an organization. These decisions typically involve high levels of risk, complexity, and resource allocation, and they often determine the organization's overall trajectory.

The Hallmarks of Strategic Decisions

• Long-term Impact: These decisions have lasting consequences and shape the future of the organization.

• High Risk/Reward: A high potential for either substantial gain or loss.

• Resource Intensive: They typically involve significant financial investment, manpower, or time.

• Complexity: Often multifaceted, requiring extensive research, due diligence, and consultation.

• Irreversibility: Difficult, costly, or impossible to reverse once executed.

Examples of Strategic Decisions

• M&As: E.g., Microsoft's acquisition of LinkedIn.

• Changing Business Models: E.g., Adobe's transition from one-time purchases to a subscription model.

• Entering New Markets: E.g., Tesla's entry into the Chinese market.

• Major Product Launches or Pivots: E.g., Apple's introduction of the iPhone.

• Organizational Restructuring: E.g., IBM's shift from hardware to cloud computing services.

• Global Expansion: E.g., Netflix launching its services in over 190 countries.

• Capital Investment: E.g., Tesla's decision to build a Gigafactory for battery production.

• Strategic Partnerships: E.g., Google partnering with NASA for quantum computing research.

• Technology Adoption: E.g., FedEx implementing autonomous delivery vehicles and drones.

Accountability

The final decision usually rests with top executives—the CEO, the Board of Directors, or the C-suite. In public companies, shareholders may get involved in exceptionally high-stakes decisions. Accountability is often at the highest levels of the organization.

But no matter what, only one person should be declared the decider and the accountable party for that decision. Have two or more deciders, and you’re done for.

Operational Decision

Operational decisions, on the other hand, are choices related to the day-to-day functioning of an organization. They tend to be shorter-term, less risky, and more reversible than strategic decisions. These decisions ensure that the organization can implement its strategy effectively.

The Hallmarks of Operational Decisions

• Short-term Impact: These decisions have immediate consequences and are often routine.

• Lower Risk/Reward: Typically lower stakes, with manageable positive or negative outcomes.

• Less Resource-Intensive: Usually involve fewer resources compared to strategic decisions.

• Simpler Context: Less complexity, often guided by established procedures or guidelines.

• Reversibility: Easier to reverse or modify if things go awry.

Examples of Operational Decisions

• Feature Prioritization: E.g., A mobile app team deciding to add a dark mode feature in the next release.

• UI/UX Choices: E.g., Airbnb deciding to simplify its booking interface to reduce user friction.

• Choice of Programming Language: E.g., A new startup deciding to build its backend services in Python.

• Inventory Management: E.g., Walmart's use of data analytics to optimize stock levels in real-time.

• Budget Allocations for Small Projects: E.g., A digital marketing agency allocating a $5,000 budget for a client's Facebook ad campaign.

• Customer Service Protocols: E.g., Zappos offering 24/7 customer support via multiple channels.

• Quality Control Measures: E.g., Toyota implementing a specific quality check at various stages of car assembly.

• Resource Allocation for Existing Projects: E.g., A software development firm assigning additional programmers to meet a project deadline.

• Employee Training Programs: E.g., A healthcare provider mandating annual re-certification in CPR for its staff.

Accountability

These decisions are often made by mid-level managers, department heads, or even frontline employees. While these individuals are directly accountable for the decision, they operate within the guidelines and objectives set by senior management.

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Don’t Become This CEO

Great CEOs define what “strategic” and “operational” decisions mean for their company—definitions, examples, protocols, how to pick a decider/accountable person, how to gather feedback, how to define worst-case scenarios, etc.

They’re clear on what types of decisions they, and only they, can make.

They’re clear on what they expect from the team and what the team should expect from them.

Unfortunately, great CEOs are few and far between. Most lack the self-awareness that’s needed to usher them into their greatness era.

Let’s take a look at what reality looks like for employees in most companies around the world.

The following four stories aren’t fictitious. They happened, and, unfortunately, continue to happen at most companies out there. Let’s see if you recognize yourself in one (or more) of these CEOs.

If you do, remember, you’re better than that. You can break out of this pattern. We’ll talk about how later.

Story #1 — The “in the weeds” CEO

Meet Jill, the Head of Product for a tech company called SoftStream . Jill is sitting in her weekly team meeting, awaiting the discussion about the rollout of the company’s much-anticipated cloud storage service. For months, her team has been fine-tuning the user experience, balancing performance, and ensuring security features are robust.

The team is wrapping up the presentation, summarizing the key milestones and timelines. Marc, SoftStream’s CEO, who asked to be invited to the meeting, says with a smile. “Great job, everyone. Now, I have to ask: How are we doing on the color scheme for the user interface?”

Emily, the UI/UX designer, looks a bit puzzled but responds, “We’ve settled on a sleek and modern design that aligns with our branding, predominantly blues and whites with accents of gray. The team feels it’s both aesthetically pleasing and functional.”

Marc tilts his head, “Hmm, I was thinking, what about adding some green accents? Green typically symbolizes growth and stability. I think it would be a nice touch.”

At this point, Jill feels uneasy. The color scheme has been a topic of numerous discussions among her team members. They’ve gone through extensive user testing and finally reached a consensus that’s backed by data. Yet, here is Marc, injecting a personal preference into a detail that the team had worked so hard on.

Chris, the lead developer, adds cautiously, “We did consider various colors, and A/B tested them. The current choice seems to resonate the best with our target audience. Adding green at this point might require additional testing and potentially delay the launch.”

Marc raises an eyebrow, “Well, it’s just a suggestion. But I do think it’s worth exploring. We can discuss this offline.”

Jill feels her team’s autonomy slipping through her fingers. The color scheme is a trivial issue compared to the technical challenges they’ve tackled, yet Marc’s involvement in this minor decision suggests a lack of trust in her team’s expertise.

In her mind, Jill echoes a sentiment that has been growing stronger with each meeting: “Why do we spend so much time discussing and researching if Marc is just going to overwrite our decisions based on a whim? What’s the point of having a specialized team if he won’t let us own our work?”

Resigned, Jill looks at Marc, “We’ll look into it and see how the green accents fit into our design.”

As she nods, she can’t help but think that this isn’t just about colors; it’s about the diminishing sense of ownership and empowerment her team feels — a pattern that seems to be becoming a part of SoftStream’s company culture.

A Closer Look

Does this story resonate? How many times have we all been in meetings where we played Marc, Jill, Chris, or Emily? This dynamic, unfortunately, is more common than we’d like to see.

Marc, the CEO, is getting involved in operational decisions that should have been left to his team. After all, that’s why he hired them in the first place, right?

Usually, CEOs like Marc behave like this because a) they care so deeply about this particular area and are unwilling to let go, or b) they didn’t hire the right people to begin with and now feel they need to overcompensate for their team’s mediocrity, or both!

Either way, CEOs like Marc chip away at their team’s confidence and trust, one meeting at a time. And over time, they’re left holding the bag when the good people leave.

A Word for CEOs Like Marc

Passion about specific areas of the company—be it product, design, or sales—is completely normal, especially if you’re a founder. That’s what made you great at the beginning of your journey. Back then, you were the one who made all the decisions. Exhilarating, I’m sure.

But as you grow your company and start hiring great people, you will have to let go of controlling outcomes in the areas you care about. If you can’t, the great people you hire will quit, or, worse, check out.

If you haven’t hired the right people and feel the need to help them make sound decisions, then you need to start there. Nothing good will come from letting mediocre teams stay in your company.

Also, the time you’re spending in the weeds, delaying operational decisions and eroding trust with your team, is time away from more urgent matters and strategic decisions that need your attention. So in effect, you’re neglecting your responsibilities to the business by getting into everyone else’s business.

A Word for Teams That Work for Marc

It’s important to sit down with Marc and set clear expectations and boundaries. Be an author and take charge. There’s no guarantee it’ll work, but you gotta do it. It’s what you can control.

Learn the art of hard conversations. Assume he’s not aware of how he’s making you feel (he’s probably not.)

If this behavior becomes the norm and if you can’t make peace with it, you might want to consider moving to a different team or leaving the company altogether. If you don’t, you risk devolving into one of these characters over time.

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Story #2 — The Underminer in Chief

Meet Joe, the Head of HR at a burgeoning tech startup called ByteWise. Joe is settling into his seat for the monthly leadership team meeting. The agenda is packed, but what concerns him most is the discussion around employee benefits. His team has been conducting surveys, gathering data, and holding focus groups to figure out what kind of benefits package would most attract and retain their talent.

After cycling through slides about quarterly earnings and marketing strategies, Linda, ByteWise’s CEO, finally shifts focus to employee benefits. “I heard your team has been working hard on this. What did you find?”

Joe is ready. He has his presentation open, full of data that strongly supports their proposed package, which includes flextime, mental health services, and a generous parental leave policy. “We’ve done extensive research and found that — ”

Before he can even finish his sentence, Robert, the COO, interrupts, “I heard some other startups are offering pet insurance. Shouldn’t we consider that?”

Joe feels a knot tightening in his stomach. “Well, we did look into that, but our research showed it was a lower priority for our team compared to mental health services.”

Linda looks intrigued by Robert’s suggestion. “Pet insurance sounds innovative and quirky. It aligns well with our brand image. Let’s include it.”

Joe feels his heart sink. His team had spent weeks evaluating and prioritizing the benefit options based on what would add the most value for employees, only to have it sidelined by an executive whim.

“Linda, our package was designed based on what we believe would have the greatest impact on employee well-being and retention. It’s tailored to our particular workforce, not just industry trends.”

Linda waves him off. “Let’s just add the pet insurance. It’ll make for a good press release, and our competitors will see we’re thinking outside the box. Oh, and make sure to adjust the budget accordingly, we can skim off the educational benefits or something.”

Feeling frustrated and disempowered, Joe thinks to herself, “Why did we bother putting in so much effort if our findings are just going to be overruled by upper management based on fads or branding? It demoralizes the team and undermines the work we do.”

Reluctantly, Joe nods, “Alright, we’ll make the adjustments.”

As he closes his laptop, Joe can’t shake the feeling that this decision isn’t just a slight to his team — it’s a signal to the entire organization that thoughtful, data-driven work can be upended by executive whims, especially when those whims pertain to issues that aren’t mission-critical. And that kind of culture, he fears, won’t bode well for ByteWise in the long run.

A Closer Look

Linda completely derailed an operational decision made by her Head of HR, and she probably didn’t even realize it. And that’s the problem.

CEOs like Linda aren't self-aware enough to realize that they cast a big shadow, and their words and actions carry a lot more weight than any other person in the company, including the C-suite.

Like Marc, Linda is chipping away at her team’s autonomy and confidence and slowing down the business by delaying operational decisions that didn’t require her input.

A Word for CEOs Like Linda

Realize that you cast a shadow and that your words matter. If you’ve delegated a decision to someone on your team, let them drive it without interference unless an egregious oversight or a threat to the business was identified as a potential consequence of that decision.

Your team will not do things exactly the way you would do them, but that’s the magic of having a high-performing team. They will do them better.

A Word for Teams That Work for Linda

Same thing I mentioned to those working for Marc. Sit down with Linda and set expectations and boundaries. Learn the art of hard conversations and do it.

Story #3 — The Unaccountable CEO

Meet Allison, the Chief Strategy Officer of a renewable energy company named GreenWave. Allison is sitting in a board meeting, and the room is abuzz with discussion about a high-stakes dilemma: whether to invest in offshore wind farms or double down on solar power installations — the company’s core business. Each option carries a different set of risks, rewards, and commitments of resources.

Allison and her team have been rigorously researching both options for months, running models and weighing variables like environmental impact, long-term scalability, and government subsidies. They’re prepared to make a final recommendation.

Before she can present her findings, David, GreenWave’s CEO, speaks up. “Before we hear from Allison’s team, I just want to say that my gut feeling is really pushing me toward offshore wind. The technology has been maturing, and it could make us industry leaders.”

Allison senses the tone of the room shifting, but she proceeds with her presentation. “Based on our comprehensive analysis, we recommend prioritizing the expansion of solar power installations for the next five years. It’s our core business, the ROI is higher, and there’s significant government support.”

David interjects again, “I’m still not convinced. What about the wind speed data for the last quarter? It’s been promising.”

Frustration builds up inside Allison. “We considered that data, but even with increased wind speeds, our models indicate that solar remains the better long-term investment.”

David looks dissatisfied. “I just can’t shake my feeling about this. Look at CleanVolt, a company half our size, raking in the dough by doubling down on wind power! Let’s revisit one more time before finalizing anything. I also think the board should vote on this.”

Allison feels confounded. Normally, a strategic decision of this magnitude would be the CEO’s responsibility, especially with so much at stake. However, David had initially delegated the task to her and her team. Yet now, he seems unwilling to let go of control, undermining months of her team’s work and creating confusion about who really owns the decision.

As she nods her agreement to revisit the analysis, Allison can’t help but wonder: “If David was going to keep such a tight grip on the decision, why delegate it in the first place? Now we have a situation where the board is divided, my team’s work is under a cloud of doubt, and our strategic direction is unclear.”

The room moves on to other topics, but Allison is still disturbed. By not allowing the team to own the decision, even after delegating it to them, David has introduced uncertainty and hesitation into a process that should be clear and decisive. It’s a failure of leadership that has implications not just for this particular decision, but for the decision-making culture of the company as a whole.

A Closer Look

Now we’re really getting into dangerous territory. David has tasked his CSO with a strategic decision yet he won’t let her make it, because, in the end, he feels it’s his decision to make but he doesn’t want to make it.

Wild, right?

I’ve seen this movie so many times it’s not even funny. This is a classic unaccountable CEO behavior right there. If this is a consistent pattern in a company you work for, RUN. It’ll only get worse. Much worse.

A Word for CEOs Like David

You shouldn’t have delegated this decision to your CSO. She should help you with input to inform your decision, which she did, but it’s your decision after all. You have to make it yourself.

You may not realize it now, but you do have a crisis on your hands. You do not trust your first team—the C-suite. I highly recommend addressing this issue asap, otherwise, you’re operating on a shaky foundation that will come crumbling down in a matter of time.

Seek feedback, coaching, and 360 reviews. Talk to your C-levels to become more self-aware of your actions and their consequences.

A Word for Teams That Work for David

Have that hard conversation and try to nip that behavior in the bud swiftly. If you’re the CSO or any other C-level who’s not fully empowered to make a decision under this CEO, you know you’re set up to fail.

Speak up, that’s your job.

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Story #4 — The Reckless Dreamer

Meet Jonathan, the Chief Operating Officer of a fast-growing e-commerce company named WebCart. Jon is in a high-stakes executive meeting focusing on a bold new initiative: expanding the company’s presence into several new international markets simultaneously.

Jon’s team, responsible for executing the operations behind such a strategic move, has been working overtime to assess logistics, legalities, and local market needs.

Steve, WebCart’s charismatic CEO, starts the meeting with an impassioned speech. “Remember, folks, projects fail when they’re thought too small. I believe this expansion can redefine who we are and elevate us to a global brand. It’s not just about increasing our market share; it’s about making a statement.”

Jon feels uneasy. His team’s preliminary research suggests that a more staggered, cautious approach would be more sensible, allowing them to learn from each market before moving on to the next. However, each time these findings have been presented to Steve, he has dismissed them as lacking ambition.

Matthew, the CFO, cautiously intervenes, “While the vision is exciting, we should consider our financial bandwidth. Spreading ourselves too thin could expose us to unacceptable levels of risk.”

Steve leans in and smiles, “I hear your concerns, Matt, but sometimes you have to risk big to win big. Let’s not let caution turn into paralysis.”

Angela, the Chief Marketing Officer, adds, “We also have to think about our brand reputation. Entering too many markets and failing would have a detrimental effect that’s hard to reverse.”

Steve cuts her off, “That’s why we won’t fail. I believe in this team, and you should believe in this vision. It’s going to be a lot of work, but the payoff is unparalleled.”

Jon can see what’s happening; Steve is not just advocating for his vision, he’s indirectly bullying his executive team into compliance. They’re being presented with a false dichotomy: either go along with Steve’s grand plan or be labeled as lacking vision and courage. The subtlety of his approach leaves little room for open dissent.

Internally, Jon is torn. “I’ve always been a team player, but this initiative is looking like a runaway train,” he thinks. “Steve is using his position to push for a strategy that I believe is operationally unsound. We’re getting strong-armed into saying yes, and it’s making me question the integrity of our decision-making process.”

Finally, Jon takes a deep breath and speaks up, “I respect your optimism, Steve, but as the team responsible for implementation, we have concerns about operational feasibility.”

Steve turns his gaze towards him, “Jon, I appreciate your diligence. But let’s not be the ones to hold ourselves back. We’ll find a way to make it work, we always do.”

It’s clear to Jon that pushing back further could put him at odds with Steve in a way that might be damaging. Reluctantly, he nods, “Alright, we’ll do our best to make it happen.”

As the meeting adjourns, Jon feels a growing sense of unease. By leveraging his charisma and position to overpower his experts, Steve has not only put the initiative at risk but also created an environment where genuine concerns are smothered by the overbearing force of his “visionary” leadership. This kind of culture, he fears, could be toxic for the company in the long run.

A Closer Look

Well, this is a train wreck. It’s obvious the company cannot handle the level of operations Steve is pushing for. Yet, he’s bullying his team into seeing, believing, and thinking the way he is. Bad news.

A Word for CEOs Like Steve

There’s a ton of cautionary tales around you. Listen and learn. You do not want to become a parable.

There’s a fine line between ambition and recklessness, courage and foolishness, inventiveness and delusion.

Livin’ on a prayer isn’t a winning strategy. Seek proof points and always ask yourself this question: “What’s the worst thing that could happen?” If the answer scares you, then take a beat and seek more feedback.

A Word for Teams That Work for Steve

It’s very hard to reason with leaders blinded by ambition, hubris, and ego. Outside of having the hard conversations and always speaking your mind, there’s little you can do to influence this type of CEO.

There’s always the option to walk, but make sure it’s the last resort. You don’t want to quit too soon if you can help it.

You Can Do Better

How do you avoid becoming a Marc, Linda, David, or Steve? Become self-reflective and self-aware.

To do that, there are three things that I’ve seen great CEOs do consistently:

#1 Read More

“Not all readers are leaders, but all leaders are readers.” — Harry S. Truman

Reading is a prerequisite for effective leadership, giving leaders a broader base of knowledge and the tools for better decision-making. It’s also the first step toward self-reflection and self-awareness.

There are plenty of books, eBooks, audiobooks, podcasts, MasterClasses, etc, that offer incredible content for new and seasoned entrepreneurs. Seek them out and start learning something new today. It will help you gain wisdom and become a better thinker, which ultimately lead to you becoming a great leader.

Critical thinking is a muscle we must always exercise. The knowledge we acquire is the protein required to grow these muscles and keep them healthy.

“The more that you read, the more things you will know. The more that you learn, the more places you'll go.” — Dr. Seuss

#2 Write Often

Writing demands a level of clarity and coherence that can improve your ability to articulate complex ideas and strategies. Through writing, you will get the clarity required for effective communication—something that was sorely lacking in the CEO profiles we looked at.

"Writing is thinking. To write well is to think clearly. That's why it's so hard." — David McCullough

#3 Get Frequent Feedback

Get a coach. Solicit feedback from your C-level and the senior executives on your team. Read more about how to receive feedback. Sometimes feedback can be difficult to hear, but it is essential for identifying issues that need to be addressed.

“Criticism may not be agreeable, but it is necessary. It fulfills the same function as pain in the human body. It calls attention to an unhealthy state of things.” — Winston S. Churchill

Final Thoughts

Being a CEO is hard. Being a great CEO is improbable, but not impossible. Put in the work to unlock your greatness.

If you don’t have the time, that means you don’t have the right leverage, which means you haven’t done the first thing all great CEOs do. Do that first, and you’ll get the time to focus on becoming the unstoppable leader you are.

I hope this was worth your time. Drop me a note or leave a comment below. I’d love to hear from you.

In Good to Great, Jim Collins contends that great leaders always start with people first before focusing on strategy or execution. That’s the “People First” approach required to take companies from good to great.

He said, “First who, then what — get the right people on the bus — the wrong ones off — and the right ones in the right seats.”

This seems so obvious — a no-brainer. But in reality, most companies are rife with people who aren’t a fit for the job, aren’t set up for success, or both. That’s because, somewhere along the line, leaders failed to do their jobs.

Most leaders mistake the “People First” approach with employee retention strategies like free lunches, yoga classes, and a 4-day work week. Although retaining employees is an important topic, the “People First” approach tackles that last.

“People First” is about hiring right, firing fast, and retaining well — in that order.

Leaders’ biggest mistake is not taking the “People First” approach seriously. It’s hands down the single most consequential mistake they’ll make.

Nothing stunts a company’s growth like having people in the boat pulling on a different oar in another direction. Sometimes, sinking the boat altogether.

”If you give a good idea to a mediocre team, they will screw it up. If you give a mediocre idea to a brilliant team, they will either fix it or throw it away and come up with something better.” — Ed Catmull (President, Pixar)

We often see wrong strategies, poor execution, and financial mismanagement as reasons companies collapse. But the truth is, these are just the consequences of failing to hire right, fire fast, and retain well. Strategies and execution don’t just happen. People make them happen.

Good leaders hire the right people and get them to stay in the boat. Great leaders do that and get the wrong people off the boat fast.

Get the Right People in the Boat

So many articles and books have tackled this subject already. What I’d like to do here is highlight the characteristics of the “right people.” There are common traits all great hires have. Let’s examine them.

“It’s easy to hire. It’s hard to unhire.” — Randy Komisar

Who are the “right people”?

To be clear, there are no absolute right or wrong people here. It’s situational. The right person for your company might be the wrong person for another company and vice versa.

Having said that, there are key traits to look for in new hires to maximize chances for success. Those traits are:

#1 Hunger: The right people have a pep in their step and are biased for action. They don’t need to be closely managed. They understand what’s expected of them and often exceed those expectations without external motivation.

They’re self-driven and contribute to the company's success far beyond the confines of their job description. When you’re interviewing candidates, try asking the following questions to identify if they’re hungry:

• What drives you to get up every morning and come to work?

• Describe a project or task where you went beyond what was expected of you. What motivated you to do so?

• Describe a situation where you identified a problem or a new idea at work and took the initiative to address it before being asked. How did you go about it?

• How do you push yourself out of your comfort zone to achieve professional growth?

• What achievement are you most proud of in your career, and why?

#2 Resilience: The right people are adaptable and deal with setbacks gracefully. This resilience allows them to thrive in challenging environments. If you run a startup, it is by definition a challenging environment. The following questions can help identify if a candidate is resilient:

• Can you describe a situation where you disagreed with a manager or team member and how you handled it?

• Can you share a piece of constructive feedback you received in a past role and how you responded to it?

• Tell me about a time you faced a significant obstacle or setback at work and how you overcame it.

• How do you keep yourself motivated during prolonged periods of challenge or stress?

#3 Critical Thinking: The right people have clarity of thinking. They have a point of view. To assess if a candidate is a critical thinker, try asking these questions:

• Describe a time when you had to make a decision with limited information. What was your approach, and what was the outcome?

• How do you prioritize your work when faced with multiple urgent issues?

• [Present a hypothetical but relevant work challenge and ask how they would approach it].

• [For the specific role] How would you handle [specific situation or task]?

#4 Growth Mindset: The right people believe they’re on a journey of learning. They read to improve their condition and always seek new skills. Here are a few questions to help identify if a candidate has a Growth Mindset:

• What skills or areas are you currently trying to develop or improve?

• How do you handle change or adapt to new situations in the workplace?

• Describe a time when a project or role changed unexpectedly. How did you respond?

• How do you ensure you’re continuously learning and adapting in your role, especially when faced with new challenges?

• Can you share a skill or knowledge area you had to rapidly acquire in response to a work challenge?

#6 Character: The right people are disciplined, honest, keep their word, follow through, and dependable. These questions can help discern if a candidate has good character:

• Can you recall a time when you had to make a decision that was right but unpopular? How did you handle the aftermath?

• Describe a scenario where you faced an ethical dilemma. How did you resolve it?

• How would your past colleagues describe your work style and contributions to the team?

• How do you handle situations where you have to provide feedback or criticism to a sensitive team member?

• Can you recall a time when you had to support a colleague going through a difficult personal situation? How did you approach it?

• What’s the biggest misconception others might have about you?

• If I were to ask your previous manager about your areas for improvement, what would they say?

#7 Passion: Finally, the right people are drawn to the company because they’re excited about its business and prospects. Asking the following questions can identify if a candidate is passionate about the company, the role, and the industry:

• Why are you interested in this role and our company?

• How would you explain our company’s mission to someone unfamiliar with our industry?

• What excites you most about the prospect of working in this industry and specifically with our company?

• How do you believe our company stands out from our competitors?

Above all, remember Frank Slootman's maxim: if there’s doubt, there’s no doubt. If you have doubts, don’t hire that candidate even if they check all the boxes.

Get the Wrong People Off the Boat

This is the trickier part of the “People First” approach and the one most leaders fail at. This is why you invariably run into victims and bullies at companies. Those people do not belong in the boat, yet there they are, sinking and taking all of us down with them.

Keeping the wrong person in the boat is far more detrimental than having an empty seat. Every time I’ve let someone go who has “institutional knowledge” and whose departure should have “ruined us,” we’d fare just fine. It’s better to have an empty seat than an occupied one that’s slowing you down, or worse.

Who are the “wrong people”?

Another reminder that there are no absolute right or wrong people here. It’s situational. The right person for your company might be the wrong person for another company and vice versa.

Also, and this happens often, some of the right people in your company will turn into the wrong people if you foster an environment that dims their light and snuffs out their creative spark. But that’s a topic for a separate post.

There are key common traits among people that do not belong in a company. These folks are dismantling your culture, so act decisively and act fast. You want to look for consistency in behavior here.

#1 Complacency: The wrong people have checked out. They’re constantly reminded to do their job. They’re lazy and often feel like the company owes them something. They bide their time until they land their next gig. These are the victims at work, and this is how you spot them:

• It’s always someone else’s fault but never theirs. No accountability.

• Putting in the bare minimum because they’re sick and tired of being surrounded by idiots (this one’s a classic!)

• They’re “working remotely” in Gstaad when their department is falling apart (true story.)

• They don’t follow through without constant reminders.

• They usually have a list of what’s not working and what other people need to do differently.

• They believe they’re doing great and do not need to change or improve their behavior.

#2 Lots of Talk; Zero Impact: The wrong people talk a big game and make a ton of promises that never see the light of day. They usually require a ton of nudging and reminding. They don’t follow through and aren’t true to their word. Here’s how to spot them:

• They promise to do [something important] by [a specific date], but never deliver it on time and usually after a lot of nagging.

• They crave the limelight without real substance to back it up.

• They rest on their laurels.

#3 Fixed Mindset: The wrong people resist change and are stuck in their old ways. They push back on learning new skills. They also feel defined by what they know today and not by how they could grow tomorrow. They’re actively or passively working to sabotage recent changes you’ve introduced.

It’s easy to spot them because they tend to balk at any new change that requires them to learn something new or work on something different.

#4 The Brilliant Jerks: This type is especially insidious. They might be good for the company in the short-term, but they’re still poisoning your culture, and you should remove them asap if you want a healthy, thriving business for years to come. These folks are easy to spot:

• They’re bullies. Plain and simple. They’re outwardly aggressive and tend to put other people down.

• They sometimes don’t have their house in order, yet they tell everyone else how to run theirs.

• They lack empathy.

#5 The Politicos: They’re the plotters at your company, spending their energy devising ways to undermine colleagues or one-up them. Their ambition is driven by unbridled ego. These behaviors can be subtle, so it might be harder to spot them, but here’s what I’d look for:

• They poison the well through gossip.

• They don’t give feedback or challenge directly. They’d rather bitch and moan about how someone isn’t doing a good job than try to have a direct conversation with that person.

Suppose you spot a person in the company consistently exhibiting the behaviors above. In that case, it’s imperative upon you — a leader in the company — to do something about it. If you’re this person's manager, remove them from the company asap.

If you managed to spot and remove these people before they cause any further damage to your culture and morale, congratulations! You’ve officially achieved what most leaders fail to do. Now you’re well on your way to creating an amazing company culture, leading to a great company, and ultimately a successful business.

Probation Period: Your get-out-of-jail-free card

Even the best leaders make hiring mistakes every once in a while. No one bats a thousand when it comes to hiring people. No one.

“In the end, you bet on people, not on strategies.” — Jack Welch

Luckily, most new hires are on probation for the first three months. If they’re not performing to expectations, the employer can terminate them without cause and with no obligation for severance or further compensation.

Assuming a high batting average in hiring great people, you shouldn’t need to use this card that often, but you must use it when warranted. This is especially important if you’re operating in Europe, where it’s much harder to remove someone after their probation period has ended.

As managers of people, we hope that the underperforming person we hired a couple of months back will perform to expectations…in time.

I hate to burst your bubble here, but that ain’t gonna happen. If a person you hired, especially a senior person, isn’t making an impact or contributing to the business in a meaningful way within the first 90 days, chances are they won’t make an impact in the next 6, 12, or however many months they’re in your company.

“When people show you who they are, believe them the first time.” — Maya Angelou

Be decisive and take action swiftly. You cannot afford not to. This is your chance to correct a situation before it becomes much harder to handle. I made that mistake before, and I swear I’ll never do it again.

Put the Right People in the Right Seats

Now that you have the right people in the boat and the wrong people off the boat, you need to ensure that the right people are set up for success.

But what does that mean?

For starters, the right people need you to continue doing your job in eliminating the wrong people from the boat. That’s the best service you could offer them.

Setting people up for success

The right people require clarity, feedback, development, and tools to do the job. Give them these four things, and you got an army of empowered teams taking your company to the next level.

#1 Clear Communication: Clearly communicate expectations, goals, roles, and responsibilities. This eliminates ambiguity and helps people understand what is expected of them.

Clarity is critical in ensuring employees are where they need to be in the org.

#2 Shorter, Candid Feedback Loops: The biggest gift you can give your team is direct, timely, frequent, and honest feedback. You must first care personally to challenge directly, as Kim Scott says. Read her book, Radical Candor, and practice giving and receiving candid feedback with your team. It’s magic.

“Clear is kind, unclear is unkind.” — Brené Brown

#3 Training and Development: Your people have a Growth Mindset and are always learning. Offer opportunities for skill development and training. This will improve their current performance and prepare them for future roles. Investing in your people is investing in your company.

#4 Provide Necessary Resources: If your people are missing essential tools and capabilities, they’re not set up for success. I’m not saying buy everyone the latest Macbook, but there’s a level of tech and tooling necessary for someone to do their job. The list varies widely based on role, but make sure they have those tools.

It’s important to note that none of these initiatives will work, and could potentially backfire, if you have the wrong people in the boat. That’s how critical it is to remove them from the environment first.

Parting Thoughts

Thank you for reading this far. Before I let you go, and for whatever it's worth, I’d like to offer some advice to the CEOs, Management teams, leaders, and employees who might be reading this post.

Advice for CEOs

As the ship's captain, you need to lead the charge on ensuring your company hires right, retains well, and fires fast. Do not delegate this work. Getting this right (or wrong) will define your culture, which will determine your destination. Nothing is more important.

Advice for Management

You are the leverage a CEO needs so she can focus on the above. If the CEO is doing your job (e.g., product, finance, business, marketing, etc,) that’s a big problem. Remember, most executives fail at this because they think they’re doing an excellent job at it. Take Change Management seriously because nothing else matters if you get this one thing wrong.

Advice for Leaders

You can do your part by ensuring your team is solid. Hire for potential and behavior, not experience and skillset. You can teach skills, but you can’t teach behavior.

Be decisive and act swiftly. You know who the wrong people on your team are. Remove them asap. That part of the job sucks, but it’s the most consequential. You got this!

Advice for Employees

If you find yourself falling into the “wrong people” behavior patterns, that’s OK. We’ve all been there. That means this isn’t the right environment for you. You deserve to thrive at work. Your job now is to find that environment that’s good for you and join it. Believe me, it’s out there.

Talk to your manager and try to find a mutual agreement for separation. You will gain great respect for yourself for having this conversation and for authoring your destiny. It’ll be good for your reputation and self-esteem as well.

The alternative of staying put, biding your time until you land a new job, might feel OK for a while, but you’re slowly dying inside. Staying at a job you clearly dislike will diminish your creativity and dim your light. You have agency. Use it to change your circumstance because you deserve to be happy.

I’d love to hear from you! You can leave a comment below or shoot me a message with your thoughts and feedback. Thank you!

Frank’s maxim is a framework for decision-making. In the context of leadership, business, and personal relationships, doubt is usually a sign that something is off. In some situations, the very fact that you have doubt is a surefire sign that you should not proceed any further. In other cases, it’s saying that more work is needed to reach clarity on the decision required.

Either way, it’s not to be ignored.

“Trust your instincts. Intuition doesn’t lie.” — Oprah Winfrey

This applies to all facets of life, not just business. Here are the ones that come to mind:

1. Hiring Decisions: If you’re considering hiring someone and something doesn’t feel right during the interview process, even if the resume is perfect, it’s often better to trust that intuition and not hire that person. Hiring decisions are the most important and consequential decisions any leader will make in a company. Hire the wrong people, and you end up with the wrong culture.

2. Joining a New Company: If you’re interviewing for a new role and everything seems to be moving along great, but you have this nagging feeling that something is off, you need to walk away from it. If you doubt the job or the company before you’ve even started, that won’t bode well for your longevity or happiness at that company. Move on and something better will come along.

3. Strategic Partnerships: If you’re thinking about partnering with another company or perhaps you’re contemplating bringing new investors on board, but there are red flags about the integrity or trustworthiness of that party, you should pause and reconsider the partnership. Doubt, in this case, is pushing you to run further diligence to get clarity on who you’re getting in bed with, so to speak.

4. Product Launches: Before launching a new product, if there are doubts about its readiness or its fit in the market, it might be worth delaying the launch to address those concerns. Don’t just power through it. Believe me, you will fail if you do.

5. Investment Opportunities: If an investment opportunity seems too good to be true, it’s usually a sign to do more due diligence or avoid the investment altogether. Sometimes your doubt is driven by your lack of knowledge. That’s actually a great thing. Warren Buffett said, “Risk comes from not knowing what you’re doing.” Educate yourself first, and after that, if you still have doubts, walk away.

6. Business Expansions: Considering expanding into a new market or starting a new revenue stream but having doubts about the potential return or the competitive landscape? This is a sign that you need to take a step back and reassess. Many epic blunders were driven by CEOs ignoring the deafening sound of intuition saying, “STOP!”

7. Relationships: If you’re in a relationship and consistently feeling unsure about the other person’s commitment or sincerity, or perhaps you’re thinking of deepening a friendship but have reservations about the person’s trustworthiness or intentions, it is a sign that a hard conversation is in order. Face-to-face communication will give you all the verbal and nonverbal cues you need to decide how to move forward.

“I rely far more on gut instinct than researching huge amounts of statistics.” — Richard Branson

Frank’s book, Amp it Up, is full of maxims like this one. I highly recommend it to all operational leaders and management teams.

Why we do what we do

“If you’re working on something exciting that you really care about, you don’t have to be pushed. The vision pulls you.” — Steve Jobs

There are two types of companies in this world: business-driven and purpose-driven.

Business-driven companies define themselves by the business they’re in. They innovate incrementally within that vertical, and for the most part, they’re not known to inspire their customers.

On the other hand, purpose-driven companies align themselves with a higher purpose — a vision that transcends financial success. They disrupt other business verticals through innovation. They’re risk-takers with a strong emotional connection to their customers.

The reason I bring this up is that I truly believe that how we choose to define ourselves has a direct impact on how we innovate, grow, and remain relevant. Most importantly, it sets the tone for how we’ll delight and inspire our customers — the fans.

We have a choice to make. We can let the prevailing perception of our company define who we are, or we can define ourselves by something far more inspiring and transcendent.

Take Pepsi, for example.

Pepsi has been a leading soft drink company for many years. They’re in the business of making and selling soft drinks and snacks. That’s the only thing they do. That’s how they define themselves.

Pepsi has innovated in that particular vertical for years — from caffeine-free and diet drinks to non-carbonated beverages. Through acquisitions and mergers, they’ve gone to great lengths to create ecosystems that support and grow their core business.

This type of sustaining innovation is great for incremental growth. Pepsi has done very well for so long, but the company’s growth has slowed down considerably in recent years, with a YoY growth rate of less than 4%. Pepsi is a business-driven company that’s maxing out its potential.

Then there’s Red Bull.

Red Bull might be widely known as an energy drink company, but it’s far more than that. Red Bull has successfully created several companies outside the energy drink space, each with its own business model and P&L.

Red Bull has its very own Formula 1 team that’s been recently sponsored by Infiniti for millions of dollars. It also founded Air Race and Media House, both of which are successful companies in their own right. Red Bull holds its own sports events, focusing on extreme sports like surfing and snowboarding. The company is worth $7.5 billion and was named one of Forbes Magazine’s Most Valuable Brands.

Red Bull was founded in 1987. Pepsi was founded in 1898.

Is Red Bull an energy drink company? Yes. Is Red Bull an action sports company? Yes. Is Red Bull a media company? Yes! So what business is Red Bull in? Red Bull is in the business of helping all of us live our lives to the absolute extreme.

Everything Red Bull does is designed to drive and support its purpose of helping all of us live our lives to the absolute extreme. Red Bull is a purpose-driven company with endless opportunities for growth.

What does that mean for us?

We, too, have a choice to make. We can choose to remain a business-driven company focused just on ticketing. Or we can choose to be a purpose-driven company and focus on a transcendent vision.

I don’t know about you, but I truly believe we can be an inspiring purpose-driven company. We need a calling that gives each and every one of us a reason to wake up in the morning and come to work.

If you ask me if Ticketmaster is a ticketing company, I’d say of course it is. Is Ticketmaster a media company? Yes. Is Ticketmaster a data company? Yes. Is Ticketmaster a tech company? Yes!

So what business is Ticketmaster in? Ticketmaster is in the business of unlocking moments of joy for fans through unforgettable experiences.

From the palpable anticipation that overtakes fans when their favorite artist announces a new tour to the confluence of emotions they feel at the venue when the lights dim and the crowd roars to the afterglow of the experience, these are all moments of joy. These collective moments are what we call the fan journey (click below to enlarge), and they’re all made possible by us.

We don’t build products for fans. We create experiences that delight and inspire them. And to do that successfully, we’ll need our tech, media, data, and ticketing capabilities to work together to drive our purpose forward globally. As we focus on driving toward our purpose, the trappings of success will follow.

My hope is that with this clear and aspirational purpose, you feel inspired to come to work every day like I do, knowing why you’re here and what you’re working towards on a daily basis.

How we do it

“All men can see these tactics whereby I conquer, but what none can see is the strategy out of which victory is evolved.” — Sun Tzu

Our purpose might seem daunting, but it doesn’t have to be. Rome was not built in a day. But with our destination clearly defined, we need to articulate which route will get us there fastest but be adaptable on our the way there.

The first step toward achieving our purpose is knowing our customers better than anyone else. To do so, we need to talk to them. Talk to the fans. Outside our offices. Out on the streets. At the venues. Understand their needs. Their challenges. We need to develop a fan-first mindset rooted in empathy and learning and commit to it.

Everything we do, every decision we make, and every feature we implement has to answer one fundamental question: how does this delight and inspire fans? We’ll need to educate our clients, sponsors, and partners on the power of purpose and help them see that when fans are happy, they win.

Our Strategy

1. Fan-first mindset: Learn as much as possible about the fans we want to delight and inspire. Understand the target personas, engage them, and measure their NPS. Test new concepts regularly with them through fan-powered events. Empathize with them.

2. Focus on experience quality: When fans use our products and run into cryptic error messages, dead-ends, or an odd flow that makes no sense, they end up having an unforgettable experience but one of frustration and disappointment. Remember Maya Angelou’s quote, “People will forget what you said and how you said it, but they’ll never forget how you made them feel.” Frustrating experiences trigger emotional reactions that leave an indelible mark in our memory. Quality matters.

3. Drive internal and external innovation: There are so many exciting opportunities that we can’t possibly deliver on alone. We must actively tap into the incredible creativity and entrepreneurial initiative many external talents have. At every devjam we’ve held, we’ve seen one or two concepts that have the potential to unlock moments of joy for fans along the entire spectrum of their journey. We must leverage this channel better to drive our purpose forward.

With clarity on strategy, we can define what we’re going to do in the short-term and long-term to deliver on our promise. Some of those tactics might not pan out, which is OK. We will evolve and adapt our tactics as we measure and learn along the way. That’s going to be part of our evolution as a learning organization.

Our Rubric

• Get out of the building

• Focus on learning fast through iteration. Perfect is the enemy.

• Value experience quality over feature richness.

• Let the data inform the way over lead the way.

• Design for global and optimize for local.

What we do

“Every little detail plays a part. Having just a vision’s no solution. Everything depends on execution. Putting it together. That’s what counts.” — Stephen Sondheim

This is where the rubber meets the road. With an aspirational purpose and a clear strategy, this should be easier than it has been in the past.

Over the next couple of weeks, we will finalize our short-term tactics and things that need to be done this year, understanding that they will be changing based on what we learn about our fans, what works, and what doesn’t along the way.

I do realize that all of this means change, which is never easy. As exciting as it is, it will also be challenging, and at times, really hard. But if we take care of each other, help one another succeed, and operate as one team–one global team–we will conquer all.

I couldn’t be more stoked to venture onto this new journey with all of you for the fan in all of us. ❤️🚀🎉

Ismail

Epilogue: Four years after that memo went out, the company launched several innovations, including Verified Fan, Smart Queue, The Harry Potter ticketing experience in the US, and many more. Purpose and customer focus pay off in the end.

When we walk into work every day, we bring our entire selves with us, warts and all. If you ignore the behavioral fluctuations we all invariably experience, you’ll realize that each of us has a signature persona in which we show up to work every day. A persona defines us in the eyes of teams, peers, and managers. We may not realize we have one, but we do.

I won’t rehash what’s already written about archetypes at work. Instead, I’d like to explore the most common characters or personas people in a professional setting embody: the victim, the bully, and the author.

Alright, let’s get right to it.

#1 The Victim

There are real victims in the world. Victims of crime, assault, and disasters. This post isn’t about them.

We’ve all been there. Feeling slighted, disrespected, and unappreciated by someone at work. Maybe you are interrupted in a meeting or passed over for a promotion you feel you earned. Maybe you just realized the company isn’t good enough for you, but you stick around until you find another “job.” Perhaps you resent your peers and think they’re incompetent.

Rings a bell?

These are examples of a victim mindset. No one starts a job wanting to be a victim, but unfortunately, many become one. The rise of victimhood culture in recent years makes this persona the most common one you’ll encounter at work. If accountability is poor or nonexistent in your culture, you will likely run into plenty of victims because unaccountable people love drama, and drama loves company.

As I said, we’ve all been there. It’s normal to feel angry or annoyed when slighted or disrespected. It’s called being human. It’s what you do after you’ve experienced anger and annoyance that determines whether or not you’re a victim.

Anger is a normal and healthy emotion that alerts us that something needs to be addressed–conversations need to happen, expectations need to be set, or actions need to be taken. Anger is good if you keep it in check and let go of it quickly.

Resentment, on the other hand, is when anger festers. It’s a sign that a needed conversation never happened, expectations remain misaligned, or a necessary action was never taken. Unresolved friction is a breeding ground for resentment, and resentment is a breeding ground for victimhood.

Accountable people address their negative emotions swiftly (and swiftly being the operative word here.) Unaccountable people let their emotions fester.

Are you a victim?

A good way to answer this question is to evaluate your resentment toward the company, a team, or a colleague. If you feel a trace of resentment, that means you’re a victim or on your way to becoming one.

If you identify with that statement, you must identify what unresolved conflicts keep you in this state of being. Find out what it is and address it. Where is this resentment coming from? Ask for feedback from the people you trust. They will help you see a clearer picture.

Once you’ve identified what it is you need to address, devise a plan to address it. Have that hard conversation with a colleague and clearly articulate your expectations. Set the boundaries you’ve been skirting around once and for all. Whatever it is. Get to it.

Actions express priorities. If you don’t act to remove yourself from the victimhood cycle, you’re actively choosing to stay in it. You have to be accountable for letting go of the built-up resentment within you. No one likes a victim. Not even victims like victims. You want to shake this persona off asap.

Here are two excellent reads for anyone struggling with victimhood and wanting a good place to start: The Obstacle is The Way and Maybe it’s You.

How to work with victims?

Dealing with victims is a delicate matter. It’s important to empathize with their pain. Victims are hurt, and acknowledging that is critical and is the right thing to do.

As a next step, I’d ask them to focus on what they can control: their thoughts, attitude, imagination, words, and actions. I’d ask them to think through the following questions: What can you do that’s within your control to address this issue? How are you going to think about it differently? What words you’re going to use to set expectations? What actions are needed to put you back in control? etc

Coaching is an effective way to help people step out of the negative cycle of victimhood and back to authoring their own destiny. Sometimes, the resentment has metastasized beyond help, in which case a different environment altogether might be the right answer.

Whatever you do, do not become an enabler. Don’t forget: misery loves company. Support, coach, but don’t get drawn into the drama.

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#2 The Bully

We’re not talking about schoolyard or physical bullying here. Physical violence should never be tolerated and must be reported asap.

Both bullies and victims have one thing in common: resentment. Victims resent when they perceive an injustice has occurred. Bullies resent when they believe that colleagues standing in their way aren’t as bright or as talented as they are. The brilliant jerk is a perfect example of a bully.

Ambition and passion are wonderful things to have, and are traits of many successful people in every field. Ambitious people tend to get things done, move mountains, and inspire others, but sometimes they get blinded by impatience, unreasonable expectations, and unbridled ego, all of which lead to bitter resentment.

When assertive, ambitious people are plagued with resentment, you get a bully. Unlike victims who are consumed with self-pity, bullies lash out with indignation.

Are you a bully?

Some bullies are self-aware of how they come across at work, but most aren’t. If you’re not sure if you’re perceived as a bully at work, ask yourself the following questions:

• Are you easily frustrated by the shortcomings of others?

• Do you interrupt people often (a sign of impatience)?

• Do you like to give blunt feedback to colleagues in public?

• Do you often think you’re surrounded by idiots at work?

• Do you sometimes dismiss the feedback you receive from colleagues?

• Do you get frustrated when people don’t see what you see?

If you answer yes to any of the above, then you are a bully. It’s important to note that although rank and seniority may exacerbate the bullying, they’re not a requirement for being a bully. There are plenty of bright, ambitious junior people that are bullies (e.g. brilliant jerks) who use their talent as leverage to justify their bad behavior.

Don’t fret. There’s a way out of this. First, you need to read Ego is The Enemy by Ryan Holiday. It’s a must-read for all ambitious, driven people, especially those with a chip on their shoulder. Then, find someone at work to be your accountability partner. You won’t go from a bully to a self-aware humble team player overnight, so having someone hold a mirror up to you as you go through this journey is essential.

Lastly, you should proactively seek candid feedback from your teams, peers, and managers. This will be painful to hear, but the only way out is through. You need to hear it, process it, and act upon it.

You can do this!

How to work with bullies?

As a first step, you need to give them the benefit of the doubt. Many people that come across as bullies actually have good intentions but their style and approach, which they may not be aware of, are sending out the wrong message.

Try having a hard conversation with that person. Make it a CLEAR (concise, logical, explicit, actionable, and real-time) conversation. It’s important to learn the art of having hard conversations to be able to set boundaries and align on expectations, so make sure you invest some time on that. Kim Scott’s Radical Candor is a great place to start.

If feedback and hard, CLEAR conversations don’t work, escalate. Make sure you let them know you’ll escalate if you don’t see a change in behavior. Being clear and firm with respect and empathy is the best policy.

“Clear is kind, unclear is unkind.” — Brené Brown

For managers and executives, it’s important to have a “no brilliant jerk” rule as part of how you live your culture to protect your company from the deleterious effects of this persona. Unfortunately, that’s easier said than done.

Many companies tolerate brilliant jerks because they tend to drive results in the short term. Not many companies are concerned about the long — term effects of toxic personas.

Most bullies get away with bad behavior, but it does catch up with them eventually. The energy you put out comes back to you ten folds. Remember that.

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#3 The Author

Price’s Law states that 50% of the result created in any organization is driven by the square root of the total group in that organization. That’s closely related to The Pareto Principle, which states that 80% of an outcome is driven by 20% of the effort (see below.)

Authors are the ones driving results. They’re the 200 people in a 1000-people company. While authors are busy driving the business forward, victims and bullies are busy shooting the breeze in the bottomless pit of drama.

Competence is linear, but incompetence is exponential.

“If you want something done, ask a busy person to do it. The more things you do, the more you can do.” — Lucille Ball

This is the persona you want to show up to work in. Authors tend to stay out of the drama triangle and focus on manifesting results for the company. They tend to focus on outcomes, coaching, mentoring, and teamwork. By their nature, authors don’t engage in gossip (not too much, anyway) and are too busy to feel sorry for themselves or lash out at their peers.

Are you an Author?

When you’re in a state of flow, you’re an author. Otherwise, you‘re spending your time being a victim or a bully. Authors tend to have a humble confidence about them that is infectious. I have had the pleasure of working with lots of authors who have shown me what it means to be one: humble, having a growth mindset, assuming they’re wrong, open to feedback, and always ready to roll up their sleeves and work.

Authors aren’t necessarily the smartest people in the room, but they’re the ones who are always asking, “How do we move forward from here?” and actually lead that effort and make it happen.

How to work with Authors?

Learn from them. Ask them to mentor you. Authors love to coach and pay it forward. Spend more time with them and around them and less time with the drama crew.

Similar to bullies, authors have high expectations of their colleagues and of themselves. Unlike bullies, however, authors will put in the work to coach and mentor others to elevate them to their level. So seek out the authors in your company. People with a proven track record of getting things done while exhibiting humility.

Be leery of the “talkers” who speak much of their past glories and all the stuff they’re going to do but never get any of it done. Those are victims in authors’ clothing.

If you’re a manager of authors, make sure you recognize them and continue challenging them. They thrive on being challenged to learn and grow. Promote and exemplify them internally. Let everyone know that that’s the behavior you expect of yourself and everyone else in your company.

We’ve all been victims, bullies, and authors at one point or another in our careers. Sometimes we go in and out of these personas multiple times a day! The question is not what persona you were yesterday or a month ago, it’s what persona you consistently show up in for your team, peers, and managers.

See, we all have a choice in how we show up to work. Do we choose to show up diminished without agency the way many victims do? Do we choose to diminish others the way bullies do? Or do we choose to elevate others the way authors do? Do we choose action or complacency? Helplessness or control? Growth or stagnation? Accountability or deflection? Courage or cowardice?

Every day, there’s a choice to be made. What will yours be?

I’d love to hear your thoughts on this.