Preface

A while ago I read four books on leadership and management and wrote summaries of them. The summaries are slightly biased in that they are mostly what I found to be useful and how I interpreted the books. I don’t necessarily endorse the points made by these books. If you are interested in management I would suggest you read these, with Managing to Change the World as my strongest recommendation.

These books mostly talk about how to manage a team of people that are being paid to do some work. If you are managing a team of volunteers, the dynamics change significantly and you, as a team leader, have much less authority over how people behave. It is important to set clear expectations with people in such a context (how many hours a week they’re willing to work is the most important variable).

Managing to Change the World

• Non-profits should be more, not less, ruthless than for-profits. For-profits focus on good organization and management because they want to make more money and being organized and well-managed is useful for achieving that. Non-profits are saving lives, and so they should be much more ruthless when it comes to achieving their goals, because so much more is at stake.
• The point of managing is to impact the world. A well-managed team is more effective as it has someone on the team who keeps the big picture in mind, oils the machine, and makes sure everyone is working towards the goal.
• The main duty of managers is to make sure that tasks get done. However, it is not in the manager's capacity to do all the tasks, so other people must do them instead.
• When delegating a task, make sure that expectations are clear. The person who was assigned the task should be able to repeat back to you what you want them to do, including the task itself, what success looks like, why it's important, and when the deadline is.
• After a task is delegated, make sure that it's progressing as intended. This might take the form of a one-on-one check-in call or an email. Do not blindly assume that tasks get done when people commit to them. People often run into obstacles and checking in can help overcome those.
• After a task is completed (or failed), keep people accountable. Make sure employees know you notice when a task has gone well or badly.
• Provide quick and private negative feedback. If someone is doing something wrong, tell them as soon as you can. Say it in private if possible, as public embarrassment causes resentment.
• What matters is what actually happens. If you're managing a team, the measure of success is not how many one-on-ones you had, or how highly people rated your management abilities. What matters is how much your team improved the world.
• Roles should clearly be pointed at the goal. Assign roles to people such that the sum of the roles assigned covers everything that needs to be done in the organization, with no gaps. One way to think about this is that every role should be optimizing for a legible set (or maybe one) of the key results of the organization.
• The organization should have clear goals and a clear mission statement. Being unified under a coherent goal is a strong collaborative tool.
• Every person should have clear goals to maximize. Goals need to be:
  • Strategic - they need to actually contribute toward making the world better.
  • Measurable - it needs to be clear at the end whether the goal has been met, either through empirical measurement or through subjective ratings.
  • Ambitious - there is a great potential in people to achieve results that are orders of magnitude better than the default. Aim to bring out this potential.
  • Realistic - Goals should make people reach for the sky, but not be so high that they are discouragingly unrealistic
  • Time-bound - Deadlines need to be clear.
• Make sure to check in on goals in regular time intervals. Annual, quarterly, or monthly reviews all work, depending on the pace of the organization (startups often do monthly).
• Goals need to be taken seriously. Executive directors need to be fighting to fulfill them, managers should hold regular check-ins for subgoals, and staff should know what they are. If they are not taken seriously, change them.
• Your current work culture shapes your future work culture. "How things are done around here" is important to get right to attract the right hires and for the organization to change the world.
• The manager should have weekly check-in meetings, and monthly step-back meetings with employees to ensure that everything is going well. The check-ins can be quick and focus on specific projects and making them go well, and the monthly step-backs serve to give a big-picture view on how the projects are contributing towards the goal.
• Competence is a general skill. The non-profit world is much less focused on individual skills than the for-profit world, and so general competence is the primary trait that is needed for star performers. The rest can be improved through investing in training.
• The best way to tell whether someone will be a good employee is to check their track record. Tests and thought experiments do not get at the crucial skill of actually making good things happen in the world.
• Invest in the growth of your top players the most. People who start off strong will grow even stronger as personal impact is a conjunction of multipliers.
• Sometimes competent people have unique weaknesses. Some people are competent at most things but bad at some. Be aware of how changeable some things are and don't invest much in the things that are hard to change. Either place people in suitable positions (that won't be affected by their weaknesses) or don't hire them.
• Conduct annual performance evaluations with all of your employees. In the meeting, tell focus on the results they achieved and what the core bottlenecks are in their growth.
• Do not promote people into positions that they're not suitable for. Many promotions involve people getting managerial responsibilities, but some people are not suitable for such responsibilities. Rather, raise people's salaries, give them harder projects of a similar type, or give them a better title.
• High salaries are cost effective if they make your employees better. The big picture is that you want to make the world as good as possible, and if having higher salaries means having superstars on your team or making your team much happier, then high salaries can be a very cost-effective broad-stroke improvement to your organization.
• You should judge a person's performance based on the performance of the ideal person that would hold their position, not against how much that particular person is capable of, when making hiring or firing decisions.
• Be assertive. Do not be a tyrant. Do not be a wimp.
  • A tyrant yells, silences others, is passive-aggressive, or makes unreasonable demands.
  • A wimp avoids tough conversations, isn't firm about expectations, isn't able to make tough calls, and prioritizes people's feelings above everything else.
  • An assertive manager is direct, calm, open to their mind being changed, fair when judging conflicts between employees, and comfortable being in charge.
• Other: When you want a task done very quickly, make it doable with one hand. If you want a quick reply to an email, make it so that the recipient will be able to reply to it while in the elevator.

The Great CEO Within

• There should be clear decision hierarchies in small teams. For any two people in leadership, it should be clear whose vote is more important. Even when the people are similarly competent, one should have a stronger voting power just for the sake of speed.
• Use the book Getting Things Done for personal productivity. Some highlights:
  • Manage your tasks (all of them!)
  • If a task takes less than two minutes, do it immediately.
  • Do not rely on your brain for information storage. Outsource this to technology. Don't split your attention.
• Document every task you do more than once, as soon as you do it the second time. This makes delegation very easy, and you will delegate more and more as your organization grows.
• Do not grow your team bigger than 6 before you have a very clear organizational goal and method. Exclusively employ people who will be very aligned and self-directed for the first few hires.
• When your team becomes bigger than 4 people, employ very clear task management systems and hierarchies. After this point, you can no longer have everyone be synced up and doing what needs to be done. It is time to document, delegate, and specialize.
• Make sure your team knows their mission. This is important for motivation during times of adversity.
• If someone calls a meeting, require that they write up their thoughts on the issue beforehand. Require that everyone write up their thoughts before a meeting. For an intermediate version of this, spend the first half of any meeting silently writing thoughts in separate google docs.
• Use OKRs (objectives and key results) and check if you're meeting them regularly. Switch them up often to avoid Goodharting.
• Onboard people very thoroughly.
• Other:
  • Take personal productivity seriously. Experiment with nutrition, health, throw money at it. There is not enough time, so make the most of it.
  • Be on time for meetings. If you think you'll run late, immediately notify others with an accurate time estimate. If people can anticipate waiting for you, then they can do much more productive work during the time they're waiting. Don't be too early as this can catch people off-guard.
  • Fun is important. If your team is hanging out and having fun together outside of work, this is a good sign. People are more productive when they're happy.
• Good quotes:
  • “You create buy-in when you make people feel that they are part of the decision and that their input contributes to the final outcome.”
  • “Agreeing on what your values are is the kind of statement that needs maximum buy-in, so it should involve your whole company. Send out a survey, and gather contributions from everyone. Ask your team to suggest both a value and the name of an employee who exemplifies it.”
  • “when receiving appreciation, there is only one correct response: “Thank you.” Do not feign humility by downplaying the act with statements like “It was nothing, anyone could have done it.” No. The person is trying to make you feel appreciated. Anything other than “thank you” will rob them of their goal.”

The One Minute Manager

• Clear responsibilities are very important for employees. Have them write them down on a piece of paper, and read through them together until you converge on a list that you agree on. Employees should have clear goals (three to six of them).
• Provide positive reinforcement immediately. A Dale Carnegie trick is to voice positive thoughts you have for other people instead of keeping them to yourself. It feels nice to get positive feedback. There is a great potential in every person that can be realized, and you can help them realize it by encouraging them to be their best selves.
• Provide negative feedback immediately. Avoid dwelling on bad feelings. If people are held accountable to their mistakes they will feel more like they matter in the organization. Frame the negative feedback within the broader context of that person being a valuable employee to remind them that you appreciate them.
• Quotes:
  • “If you can´t tell me what you'd like to be happening, you don't have a problem yet. You're just complaining. A problem only exists if there is a difference between what is actually happening and what you desire to be happening.”

The Culture Code

• Vulnerability is important. People should be honest about what they feel and think about what's going on.
• Safety is important. People should feel like they belong in the group and that others will have their back, support them, and trust them.
• People should know the purpose of the organization and how it's making the world better. Having a clear mission statement that people can recite can be a strong anchor in times of adversity.
• Physical proximity is important for teams to sync together. This becomes less sustainable for team sizes bigger than 4 people (because of distractions), but for small teams, aim to have them in the same room as much as possible.
• Prepare for worst-case scenarios and do murphyjitsu. Be prepared for all to fail and to face failure without flinching away.
• Good quotes:
  • When giving negative feedback or communicating expectations: "I’m giving you these comments because I have very high expectations and I know that you can reach them"
  • “Belonging cues are behaviors that create safe connection in groups. They include, among others, proximity, eye contact, energy, mimicry, turn taking, attention, body language, vocal pitch, consistency of emphasis, and whether everyone talks to everyone else in the group.”