A Leadership Primer

This is my running list of guiding principles for being a good leader.

This concept of managing extremes is covered well in The Dichotomy of Leadership.

  • Leadership is about managing extremes: empowering vs. micromanaging, mentoring vs. firing, discipline vs. freedom, leadership vs. following, and planning vs. creativity.

  • Be available at all times. Be someone that they text or call when something is on their mind.

  • It’s positive to treat your team like your children in at least one crucial sense: their success is your success. If you are challenged or insecure about their thriving (even above yourself) then you are not centered enough as an individual to be a manager.

  • Of all the things you reward and punish, reward when team members help each other at some expense to themselves, and punish when team members take a benefit at some expense to a team member.

  • If something happens and food is scarce, eat last. If something happens and you have to stay late, be the last one to leave. If only your team or you can get a bonus, give it to them. Take bullets for them and they’ll take bullets for you.

  • Make sure the team knows that honest disagreement and challenges are encouraged, but that undermining, backstabbing, and general toxicity directed at fellow team members is a one warning offense. If it’s seen again they should be immediately removed from the team and/or the company.

  • Be consistent and dependable. If you tell them you’ll do something, make sure you do it.

  • Take responsibility for your team’s mistakes. If a nuke is coming down to hit one of your people, step in front of it. Let management know that you have the situation under control and don’t let the hit go through to your employee.

  • Nurture a healthy relationship with failure for the team—especially if you commonly attempt to do tasks that are difficult to attain. Remind them that failure is often the currency of success.

  • Be someone who people would follow even if they didn’t have to. If people listen to you only because they work for you, you’re an authority not a leader.

  • Judge yourself by the success of your employee in later roles. Are they happier, more confident, in better positions, making more money? If so, you’ve likely done well.

  • In most situations—especially brainstorming—you should interact with your employees like peers. You may be making the final decision, but you should listen to input as if any of you could be making the final call.

  • Employees should worry about disappointing you, not being fired. A team motivated by fear is an unhealthy team.

  • A-players who are feeling afraid, insecure, and psychologically unsafe in the work environment will instantly become C-players. This applies to teams as well. People and teams can only function at their A potential if they feel safe and supported.

  • Feeling safe is different than feeling comfortable. Teams and individuals should always be somewhat unhappy with their current state relative to where they want to be.

  • Never discipline while angry. Think before you act.

  • If you ever have to let anyone go, make it clear to them that life is about fits. There are great people who simply don’t fit in a particular role at a particular time. Remind them that failing at a position and failing at life are not the same.

  • Great leaders make their team members feel psychologically safe.

  • Great teams are teams that are empathically tied to each other, and are comfortable sharing their insecurities and weaknesses, where failures and successes are shared.


  1. This should be obvious, but some of these are slanted towards my own perception of good leadership. Bias, experience, and personal preference are in play.

  2. This list is based on fairly advanced careers involving mature adults. Many of these points don’t apply to managing 15-year-old fast-food workers, for example.

  3. For the failure point, it’s all about context. If you are an ops manager and you have SLAs, failure there isn’t a currency of success; it’s just bad. This is more for new ideas, innovation, taking a chance on a business idea, etc.

  4. @jockowillink on great leadership: 1) humility and coachability, 2) managing the dichotomy of leadership, and 3) taking responsibility.

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