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.