How to Be an Asshole, Respectfully I used to think being a good leader meant being liked. For years, that strategy worked. I built strong relationships. My teams performed well. People trusted me. I thought I'd figured out management. Then COVID hit. Overnight, our business effectively went to zero. We weren't dealing with bad execution or a failed strategy. The world had simply changed. We laid off roughly half the company. I had to let go of half my own team on a single day over Zoom. I can’t even remember exactly how many conversations I had. They were non-stop. Back-to-back for 12 hours straight starting at 6 AM Pacific. I think I laid off 15 people in a row. Many cried. Afterward, I helped rebuild the organization, and eventually we recovered. But it crushed me. Not because I disagreed with the decisions. They were necessary. The company survived because we had the courage to make them. It crushed me because I wasn't prepared for what leadership feels like when there are no good options. After the layoffs, everyone was unhappy. Nobody got raises. High performers left because they couldn't get promoted or paid more. Every conversation became harder than the last. My marketing budget was gone. We had to negotiate clawbacks from vendors on stuff we had paid for that was canceled. Brutal doesn’t even begin to describe it. For the first time ever, I felt like a failure. But I wasn't failing because I lacked empathy. I was failing because empathy had become an insufficient operating system. Looking back, I don't think I would have made different decisions. I'm not even sure I would have led differently. What I question is everything I'd been taught about leadership before that moment. Every book, training course, and workshop on leadership was about helping people thrive. That's excellent advice until reality stops cooperating. Nobody tells you what leadership looks like when there isn't enough money for raises. When layoffs are inevitable. When every available option is bad. When your job is no longer to make people happy, but to decide who bears the pain. That's when I started wondering whether I'd been optimizing for the wrong thing all along. Almost none of the books I had read asked a harder question: How do you lead when nobody thrives? What do you do when every option is bad? When every decision hurts someone? When your job isn't to maximize happiness, but to decide who bears the pain, when, and why? That's a very different kind of leadership. It's also the kind almost nobody writes about. This isn't a guide to being an asshole. It's a guide to leading when there are no good options. Sometimes those are the same thing. 1. Someone has to lose This is the first thing nobody tells you about leadership. Every meaningful decision creates a loser. Someone doesn't get promoted. Someone loses budget. Leadership books are obsessed with win-win solutions, but eventually every leader finds themselves in a situation where the game becomes zero-sum. There simply isn't enough money, enough time, or enough opportunity for everyone to win. Your job is no longer to make everyone happy. It's to decide who loses, why they lose, and whether the organization is better off because of it. The worst leaders aren't the ones who make painful decisions. They're the ones who postpone them because they're unwilling to decide who loses. 2. Kindness is not the absence of pain A surprising amount of management advice boils down to making people feel good. That's fine when business is booming. But there are times when hard decisions need to get made, and they will hurt someone. The goal isn't to eliminate pain. It's to make sure the pain serves a purpose. Lay someone off because the company won't survive otherwise. Kill a project because the resources belong elsewhere. Say no because saying yes would be dishonest. Pain with a purpose is leadership. Pain without a purpose is cruelty. 3. Know what game you're playing The leadership that gets a startup from 20 people to 100 is not the same leadership that gets it through a recession, a failed product launch, or a massive restructuring. Startups don't just grow. They evolve. The constraints change, the tradeoffs change, and your job changes with them. The mistake is assuming that because yesterday's playbook made you successful, it's still the right one today. Often the hardest part of leadership isn't changing the company. It's changing yourself before the company forces you to. 4. Avoiding conflict compounds Every conversation you postpone gets more expensive. Every problem you avoid becomes someone else's emergency. The employee you should have managed out six months ago slowly poisons the culture. The product you should have killed consumes another quarter of engineering time. The strategy you know isn't working gets harder to abandon because you've already invested so much in it. Delay doesn't reduce pain. It redistributes it, usually onto people who didn't create the problem. 5. You are not responsible for everyone's happiness This was the hardest lesson for me. I thought leadership meant absorbing everyone else's disappointment. If people were upset, I felt like I'd failed them. If morale was low, I took it personally. It doesn't work. You can't carry everyone's emotions and still carry the responsibility of leading. Sometimes people are unhappy because reality is unhappy. Your job isn't to make them feel better. It's to help the organization survive long enough that there will eventually be something to feel better about. 6. Optimize for the business, not popularity People can survive bad news. They can survive layoffs, missed promotions, canceled projects, and budget cuts. What they struggle to survive is randomness. Explain your reasoning. Apply the same standards to everyone. Be predictable. Fairness builds trust. Popularity is rented, and the lease expires the moment resources become scarce. 7. Get comfortable being the villain If you lead long enough, someone you respect will think you failed them. They'll tell the story from their perspective, and you'll sound like the bad guy. That's part of the job. If your need to be understood outweighs your willingness to make difficult decisions, you'll slowly start managing your reputation instead of the business. 8. Protect the mission, not your image We admire Shackleton because he brought every member of his crew home alive. We rarely ask whether that makes him a useful model for building companies. Businesses exist to accomplish a mission, not simply preserve themselves. Sometimes protecting the mission requires sacrificing the team. Sometimes protecting the team destroys the mission. Leadership is deciding which one you're actually responsible for, even when the answer makes you unpopular. 9. Machiavelli wasn't writing for middle managers He was writing about what it means to hold power. His insight wasn't that leaders should be feared. It was that leaders can't organize their decisions around being loved. The moment your identity depends on everyone's approval, you've outsourced your judgment to the people you're supposed to lead. 10. Learn to be an asshole, respectfully Not the kind who humiliates people. Not the kind who mistakes cruelty for strength. Become the kind who's willing to make the difficult decision before circumstances make it for you. Tell the truth before it becomes unavoidable. Protect the mission even when it costs you personally. If you play this game long enough, someday, someone will eventually call you an asshole. If you're lucky, they'll only be half right. The older I get, the less interested I am in being liked. I'm much more interested in becoming the kind of leader who can do what's required when there are no good options. If that means someone calls me an asshole, I can live with that.