21 management things I learned at Imgur

Sam Gerstenzang
4 min readJun 18, 2015
  1. It’s terribly difficult to manage unmotivated people. Make your job easier and don’t.
  2. Different people need different kinds of management. Be adaptable to figure out what drives each person’s best performance.
  3. Give feedback frequently and directly. As a manager, it’s easier to wait and then hedge critical feedback in soft wrappers, but that’s selfish. I’d try to give feedback as soon as I could grab a conference room with the person, and not wait until the formal 1:1 days later.
  4. A-players love hearing critical feedback about how they’re performing, and they hate when B-players don’t hear feedback of their own. Keep your A-players happy by providing actionable feedback to everyone and recognizing superior performance.
  5. Communication is the most difficult thing you’ll do. Spend a lot of time on it, both on your own communication and improving the communication of the folks on your team.
  6. Fire quickly. If you don’t fire bad performers fast, you’re at risk of losing your good performers. Don’t underestimate the effect bad performers have on good performers. Your team will likely move faster even with fewer bodies. Finally, firing for bad performance is easier than having to fire good people because you’ve run out of money, so fire the bad people before you have to fire the good people too.
  7. People need to feel like they’ve been listened to, not to make the final call. Take the time to listen (you might be wrong), make a decision and then explain the decision. Don’t offer commentary on others’ decisions until you understand why the decisions were made.
  8. Providing context for why you made a decision is a way to scale your decision-making process. The goal is for the manager to make as few decisions as possible, and to do this, your team needs to understand how to make good decisions.
  9. Define success clearly and don’t flip-flop on the definition without new information. On the other hand, when the facts change, re-evaluate your goals. Set achievable but difficult targets.
  10. Hiring friends can be very useful because communication will be easier, and your friends are probably smart and talented. But you might do so at the cost of hiring for things like experience or domain-expertise. If you can’t fire friends, don’t hire them.
  11. Mission-oriented teams are a competitive advantage because they make it easier to 1) hire and 2) motivate.
  12. Any action taken between a manager and an individual (a promotion, more frequent 1:1's, a call out in a meeting) is not just between the manager and the individual, but affects every person on the team. For example, if you promote one person, make sure the rest of the team understands why that person was promoted and what needs to be done to achieve the same.
  13. You’re more likely to lose by not recognizing your weaknesses than from the presence of weakness, so aim for self-awareness.
  14. Sometimes you’ll have to bet on big, resource intensive projects that won’t work. Be careful of the morale toll on your team. Not everyone has great tolerance for repeated failure. If you’re a founder, you probably are more used to this than your team. One technique is to mix iterative work with riskier bigger bets to rebuild this energy. But you should also try to not paint any feature as a silver bullet, and individual failure in good faith as a necessary cost of trying new things. Your company is a portfolio bet.
  15. How you spend money is one of the biggest cultural signals you can send and is very hard to change. Where you spend money (and where you don’t) communicates what you think is important.
  16. The best way to avoid politics isn’t to ignore politics, but to spend your time on it. Define clear merit-based systems, which reduces confusion about what your team members need to do be recognized.
  17. One of the most helpful things you can do is remind the team of the bigger picture. Knowing what’s important will help cut through the bullshit.
  18. The best way to manage great people is to provide clarity of purpose and regular feedback (which is different than regular direction).
  19. While career development is ultimately the responsibility of each individual (who else?), time spent as a manager to proactively understand and enable growth is time-well spent.
  20. Sometimes people talk shit. Sometimes people have bad days. Don’t take either personally.
  21. A personal mantra I’ve found useful is “we were lucky but now is the time to be good.” That is to say, let us pretend that all past success was the result of our situation and not our own hard work or good qualities. We now have a unique opportunity to reduce our dependence on luck through superior performance. There is no cost to this belief except your ego, and it can help drive radical self and team improvement.

Thanks to Wagon for providing a desk and copyediting.



Sam Gerstenzang

Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z http://samgerstenzang.com