37 Leadership Lessons Learned in 37 Years
Today I turn 37 years old. Throughout my career, I’ve gotten to do a lot of challenging things, such as joining a startup as their first U.S. hire, building manager training programs from scratch at multiple companies, and leading teams as large as 160 people.
I’ve made countless mistakes and also celebrated satisfying breakthroughs. Looking back, here are 37 leadership lessons that stand out—split out by subtopic.
Re: Communication
1. Bad news ages like fish—not wine. If you have to share bad news, dish it early. For example, if you have to tell your boss or the board that you lost a key client, didn’t close a big sale, or blew up a negotiation, tell them yourself before they hear it from anyone else.
2. Give feedback early and often. Leaders have a responsibility to share the hard news. That’s your job. The more you give feedback to your team (as well as receive it), the less scary it will be for everyone.
- Feedback given 1x/year during performance reviews = Scary
- Feedback given 1x/week during 1-on-1s = Not scary
3. Say what no one else will say. Too many people (and companies) tiptoe around difficult topics. Be the person who speaks the unpopular truth. Author Susan Scott calls this exposing the “ground truth” rather than agreeing to the “political truth.” Unspoken ground truth can kill a company.
4. Leadership, respect, and attention flow to the best speaker in the room. In some video games, you can choose which skills to maximize for your character: speed, agility, strength, etc. In the game of business, it pays to invest your character points in speaking ability. People want to follow someone who can clearly and confidently express ideas.
5. Sit on the same side of the table. In any disagreement, it’s easy to approach the conversation with a “me versus you” mentality, as if you’re on the opposite side of the table from the other person trying to win a battle. But if you mentally shift your perspective to think of yourself as being on the same side of the table as the other person — collectively trying to solve a common problem — the conversation goes much better.
6. When in conflict, speak softly. Former FBI hostage negotiator Chris Voss recommends using “late night FM DJ voice” when talking to someone who’s getting heated. If you calm down and soften your voice in a disagreement, the other person will often do the same. Their mirror neurons kick in and they unconsciously copy your demeanor and tone.
Re: Performance management
7. Hire slow, fire fast. Who you choose for your team is the most important decision you’ll ever make as a leader. When interviewing someone, treat a “maybe” like a “no.” Every hire should raise the mean and make your company better. And if it’s clear in a new hire’s first few weeks that they’re not a good fit, save yourself (and them) the heartache by parting quickly.
8. Ask the million-dollar question. Whenever you’re trying to decide whether to keep a struggling employee, ask yourself, “Knowing what I know now, would I enthusiastically re-hire this person?” If the answer is no, let them go.
9. Reward loyalty. If someone proves to be a good fit for your team (which hopefully happens WAY more times than not), invest in them. Give them new challenges so they can learn something new every day, then pay them for that increasing knowledge. A good employee is an appreciating asset: they become more valuable the longer they’re around because they know the ins and outs of the company.
10. Give each of your direct reports an inspiring theme for the year. Performance reviews are usually forgettable or demotivating. Make each employee’s review more impactful by sharing a one-sentence guiding theme that can serve as their inspirational North Star for the year ahead (e.g., “Set the standard for excellent customer service for our company” or “Become the go-to resource for Excel knowledge”).
11. For high performers, expand the circle. Once an employee proves they can perform their job at a high level, they earn the opportunity to take on greater responsibility. Give them opportunities to train and mentor the rest of the team. And once they prove capable in that, find ways to get them in front of the entire company: leading training, sharing in All-Hands, etc.
Re: Delegation
12. Stop doing your old job. It’s easy to fall into old habits and continue performing aspects of your last job even after you’ve been promoted to management. Your old responsibilities feel comfortable while management can feel scary, but you need to lean into the scary. You don’t have time to do both jobs. Trust your team with those old tasks.
13. Be in the weeds, but don’t own the weeds. My old boss Annie gave me this advice, and it stuck with me ever since. Stay connected to the work, but you shouldn’t be the primary person responsible for most of it. Again, trust your team.
14. Rethink your busywork. What’s “busywork” for you may be a stretch assignment for someone else. Keep your eyes open for assignments that others on your team haven’t done before. By delegating those tasks, you can eliminate work from your plate while helping employees learn new things.
15. Delegate more than just tasks. It took me a long time to realize that I could delegate not only tasks but also decisions and meetings. If someone else can make a decision that’s at least 80 percent as good as the one you’d make, in many situations, that’s good enough. Let them try it their way. They’ll learn from the experience.
Re: Personal development
16. Inhale knowledge. The day you stop learning is the day you become a stagnant leader who’s not worth following. As John Wooden said, “Drink deeply from good books.” Listen to podcasts. Read articles about leadership and personal development. Become someone worth following.
17. Treat knowledge like breathing. Every insight you learn should be passed along to others. Breathe in by absorbing books, TED talks, and life experiences. Then breathe out by sharing those tips with your team.
18. Share both successes and failures. No one likes the person who only shares their wins. Exhibit vulnerability by also telling others about your mistakes. If they make the same lessons you did, you’ve failed them.
19. Run toward the fire. If you see a project that looks scary or something you haven’t done before, raise your hand. Volunteer for the toughest assignments and you’ll be rewarded with experience, wisdom, and higher pay. Become known as the person who can solve the gnarliest problems.
20. Take time to self-reflect. Journal about your successes, failures, and lessons learned. Set aside time every week to reflect upon what you learned that week — including the stories you experienced that can be marshaled into future lessons for others (through writing, speaking, etc.).
Re: Relationships
21. Be efficient with processes and effective with people. Efficiency is a worthwhile aspiration when trying to solve process problems (writing software code, building a spreadsheet, designing an assembly line, etc.), but it’s the wrong driving force when dealing with people. In relationships, focus on quality and authenticity rather than quantity and productivity.
22. Don’t roll shit downhill. Your boss may take out their frustration on you sometimes. You can’t do much about that, but you can control whether you spill over that same frustration onto your team members. Shield your team from stress rather than serving as a conduit for it.
23. Ask about life outside work. Most 1-on-1s should include time to discuss non-work topics. If you don’t know the name of your team member’s spouse, kids, or pets, you probably need to ask more questions about life outside work. If they don’t want to share, that’s fine, but your ignorance shouldn’t come from a lack of caring or asking.
24. Work and life bleed into each other. Anyone who thinks that work and life can be kept totally separate is fooling themselves. If your team member’s relative just died or their cat is in the vet, that will impact their work — and that’s okay. Remember, you’re managing humans — not robots.
25. Assume positive intent. When someone does something that annoys you, it’s easy to jump to conclusions and judge them as lazy, mean, or ignorant. Resist that temptation. Instead ask yourself, “Why would a reasonable, rational, and decent person do what this person is doing?” (Source: Crucial Conversations)
26. Respect those not in the room. You’ll be put into many situations where it’s easy to blame or talk bad about someone else. Rather than piling on, become known as someone who speaks up for those not present.
27. Mentor AND be mentored. At every point in your career, strive to pair up with someone who’s out in front of you (a mentor who can guide you) and someone who’s a few steps behind you (someone you can mentor). Each will challenge you and stretch you in different ways.
Re: Asking questions
28. Recognize the power of the questions you ask. As David Brooks says, the quality of your questions determines the quality of your conversations. This is doubly true for leaders because it’s your job to ask thoughtful questions in meetings and 1-on-1s. Take time to choose the right questions.
29. Prepare specific questions for each meeting you lead. A question that is 20 percent better can yield an answer that is 200 percent better. Questions are a high-leverage tool, and you should wield them to generate the best insights from your team. Carve out 10–15 minutes before each meeting to strategize the right questions to ask.
30. Ask “what” and “how” questions. “Why” questions tend to put people on the defensive (e.g., “Why did you do that?”), whereas “what” and “how” questions open up the flow of conversation (e.g., “What are the pros and cons of approaching the problem that way?”).
Re: What to avoid
31. Beware of the curse of knowledge. As Chip and Dan Heath explain, the more you know about a topic, the harder it is to remember what it was like to first learn that topic. When describing complex topics to your team, overcome your expertise by using analogies and avoiding jargon.
32. Beware of unfamiliarity bias. When choosing whom to promote, it’s easy to fixate on the faults of the people you’ve worked with and opt for an outside hire for the role. (After all, you haven’t seen that outside hire screw up anything, right?) This is flawed logic. Promote internally when possible.
33. Beware of ivory tower syndrome. As you climb up the ranks in your company, you’ll get disconnected from the day-to-day work. That’s natural, but that disconnection can be disastrous if you don’t ask your team for ideas and feedback before making big decisions. Stay connected to your team and the work rather than blindly telling others what to do.
Re: Self-discipline
34. Block out time for key projects. If you’re not careful, “shallow work” like emails, Slack messages, and meetings will suck up all of your time. Make time for “deep work” by time-blocking slots of 90–120 minutes in your calendar. Use that time for strategic thinking and important tasks.
35. Close every loop. You can immediately put yourself in the top 10 percent of any group by taking good notes, following through on commitments, and closing communication loops (“You asked for this by Wednesday and here it is.”). Keep your word, even in the little things.
36. Relentlessly single-task. The number of tabs open on your web browser is a good proxy for how divided your attention is. No one can remain focused and efficient with 30+ browser tabs open. Choose one thing to do, then complete it. Then move on to the next.
37. Nothing gets done without routines. The most successful and productive people are often predictably boring. For example, every morning they wake up at the same time, go on a run at the same time, and eat the same breakfast they did the day before. Boring is consistent. Boring is effective. Boring pays off.
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