Notes on The Art of Leadership: Small Things, Done Well by Michael Lopp

The Art of Leadership Cover

I owe a lot to Michael Lopp. Years ago, his book, Being Geek, and his blog, Rands in Repose, were my first introductions to thinking about software engineering and engineering management as a capital letter “C” Career. And they were my first introduction to the concept of regular 1:1s and other fundamental management concepts. What I learned from him allowed me to avoid creating a total disaster of everything when I was made a manager with no training. Where I am in my career right now, I can trace back to what I first started learning from Lopp, and I am still learning from him today.

(Thank you!)

That is all to say that I recommend The Art of Leadership: Small Things, Done Well (and his other writing) to anyone in software engineering management, or considering software engineering management. Most of the book is adapted directly from Rands in Repose, so you could get some value from browsing the archive. That said, he’s selected the best material, refined it, and added entirely new chapters, so I recommend reading the book.

Lopp’s signature technique is to tell a story to illustrate his point. This technique is compelling, engaging, and works well.

Most useful chapters

I found the following chapters most useful:

  • 2. Meeting Blur
  • 7. A Performance Question
  • 8. How to recruit
  • 9. Rainbows and Unicorns
  • 10. Say the Hard Thing
  • 11. The Signal Network
  • 12. Be Unfailingly Kind

Resonating concepts

The following concepts resonated the most with me:

  1. Information dissemination is a core responsibility of a manager.
  2. A manager should set the highest standard for follow-through.
  3. Recruiting is a core responsibility of a manager.
  4. Compliments work.
  5. Say the hard thing. Your goal should be to make feedback routine.
  6. As a leader, it’s ok to selectively lean on your experience instead of working to gain consensus.

These concepts are critical. So much so that I hope to write about many of these separately, bringing in other sources. For now, I’ll briefly discuss what Lopp says about each, and use each as a vehicle for me to expand a bit.

1. Information dissemination is a core responsibility of a manager

My educated guess is that 50% of my job as a manager is information acquisition, assessment, and redistribution. It is my primary job, and the efficiency with which I do this directly contributes to the velocity of the team.

You can spend a lot of time and money investing in processes, tools, and artifacts that you believe are necessary to critical and timely information flow, but where I consistently invest is in the team. I demonstrate to the humans the value of effectively detecting, assessing, routing, and retransmitting information across the organization.

A manager has access to a lot of information that the team doesn’t have about what’s going on elsewhere in the company, for example in a high-profile meeting. As a leader, you have a responsibility to communicate this to the team to help them work more effectively.

I’ve been thinking a lot about this one lately. Communication is the challenge of a growing team. The number of possible 1-1 communication channels increases proportionally to the square of people. As your organization grows, you start to need new layers in the form of middle managers to tie things together, which introduce even more communication channels—and opportunities for communication to not happen.

Ideally, you can organize teams so that the right people naturally talk to each other, establish mature project management, organize structurally recurring meetings (daily standups, etc.), and foster a culture of communicating well in writing through tickets. But… as experience shows, there are always gaps. It’s a manager’s job to actively seek out and fill those gaps.

2. A manager should set the highest standard for follow-through

“You sign up for things and get them done. Every single time.”

I liked this so much that I already quoted it. A big part of being a manager is nudging people to the behavior you want through setting an example of that behavior. Follow-through, in particular, is so fundamental because it is the foundation of trust. You do what you say. What you say means something. People can rely on you.

3. Recruiting is a core responsibility of a manager

On the list of work you can do to build and maintain a healthy and productive engineering team, the work involved in discovering, recruiting, selling, and hiring the humans for your team is quite likely the most important you can do.

Lopp advocates spending at least one hour per day on recruiting-related activities, up to 50% of your time. That’s a lot! But, this is something I believe in and have advocated for myself. Will Larson has written about spending time each week on cold sourcing.

The critical point here is that growing the team, in the right way, is the manager’s responsibility (and I would argue accountability). The composition of the team is one of the most significant factors that will determine the team’s future performance. Too many managers rely on HR to do everything in recruiting, but that’s an abdication of responsibility.

You can rely on you HR/recruiting team as a powerful partner to do the actual work of traditional screening, recruiting, etc. but you need to be involved. Since you are closer to the work, you are better positioned to have the meaningful conversations with candidates that can truly identify who the best match is, and more importantly, communicate to the candidate in their language why they should want to work at your company, and with you, personally.

Lopp identifies three stages of a recruiting pipeline for engineering managers, which differs from the traditional recruiting pipeline:

  1. Discover. Networking and cold sourcing.
  2. Understand. During the candidate interview process, your goal here is to make sure that the candidate understands your mission, culture, and values.
  3. Delight. From offer to onboarding. Just because a candidate accepted an offer doesn’t mean that they will show up on the first day. After a candidate accepts an offer is a dangerous time, where the reality of impending change hits them, and doubt and uncertainty are at their most intense. Stay engaged with the new hire through meaningful, personal communication. Describe to them what they will be working on. Don’t rely on HR to be the sole communicators with the candidate.

4. Compliments work

People like compliments; they make them feel good. It is a form of timely feedback that helps people learn. Lopp gives a useful, practical definition of a compliment as a “a selfless, well-articulated, and timely recognition of achievement.”

All of those components are important, but the most important to me is “well-articulated.” Don’t just say “good job.” That’s easy to toss off, and the recipient knows it. It’s cheap. Specifically state the act, the value, and the impact. It shows your paying attention, and it communicates what you value, and what the team values.

This resonates with me because frankly, like most managers, I don’t do this enough.

5. Say the hard thing. Your goal should be to make feedback routine.

Feedback is an incredibly valuable social transaction. It shows that people have taken their time to observe an aspect of you. They have other things to do, but today they are investing in you. You think you’ve got it all figured out, but you don’t. In turn, you take the time to clearly hear the feedback, ask clarifying questions, and hopefully adjust the way you work. All the constituent parts of the act of giving and receiving feedback provide an opportunity to build trust in a relationship.

There are two parts to this. First, say the hard thing. Since reading this book, I’ve kept this phrase in my head.

The ability to say the hard thing is a critical leadership skill. It is essential to helping your team grow. Positive feedback (compliments!) can go a long way, but sometimes you have to tell someone something they don’t want to hear. It’s easy not to say the hard thing because we don’t want to hurt someone’s feelings. We know that we wouldn’t want to hear it, so we don’t want to say it. However, as I have learned from personal experience, the only thing worse than saying the hard thing is not saying it.

Another way I like to think about this is that you should tell people what they need to hear, not what they want to hear. More bluntly: avoiding a hard conversation is selfish, because you are putting your own emotional comfort above your responsibility to help the person grow, your responsibility to other team members who deserve the best teammates, and your responsibility to your employer to guide the team to achieve great performance.

The second part is making feedback—saying the hard thing—routine, so it is a bit less hard to say. It’s an essential behavior to model and foster. It takes practice, and it isn’t easy. A team that can talk to each other candidly about what is going well, and what is not, is a team that trusts each other, and a team that will do greater and greater things.

6. As a leader, it’s ok to selectively lean on your experience instead of working to gain consensus

This is a bit of a corollary to avoiding the  “not invented here” syndrome.

As you advance in your career, one advantage you gain from experience, and from being an executive, is that you can selectively draw on that experience to shortcut what would potentially be a long discovery and decision-making process. The example he uses is that he adapted a career latter from a previous gig instead of working collaboratively with the team to create a new one. It wasn’t necessarily as good of a fit as a custom one would have been, but it was much faster to produce. The team was able to focus on higher-value work.


The Art of Leadership is valuable for both new and experienced engineering managers for different reasons. For the new manager, these concepts and the stories that frame them can help form some of the mental matrix you use to orient yourself as you face new situations. For the experienced manager, Lopp has a way with words and a way with framing that can help clarify your thinking, even if you already know the specific concept under discussion.