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Q&A on the Book The Art of Leadership

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Key Takeaways

  • Leadership is a career restart.
  • The most important skill early leaders need to learn is how to delegate.
  • Leadership, like any skill, requires a lot of practice. 
  • Find a set of leadership habits that you want to focus on. Do them a couple of hundred times and see what you learn.
  • Leaders fail like everyone else.  

In the book The Art of LeadershipMichael Lopp shares stories of leadership habits and practices. Examples include reading the room, getting feedback, delegation, giving compliments, understanding the culture, and being kind. In the book Lopp describes how he practiced and refined these leadership habits over the years and what he has learned from doing so. 

InfoQ interviewed Michael Lopp about reading the room, using spidey-sense to render decisions, mistakes that leaders make, delegating until it hurts, having regular staff meetings next to 1:1 meetings, conducting distributed meetings, fostering anti-flow, how leadership is a set of principles, and advice to engineers who are promoted to management,

InfoQ: Why did you write this book?

Michael Lopp: I became interested in the habits of leaders I’d worked with and respected and was documenting both habits I’d observed and also applied. As this list grew, I realized that the value wasn’t in acquiring and trying a habit, it was the lessons a leader learned from applying those habits a lot, for years, with consistency. With that thought in mind, I knew I had a book.

InfoQ: For whom is this book intended?

Lopp: This book is intended for all types of leaders. No prior leadership experience is necessary. I chunked the book into three acts: manager, director, and executive for those leaders who want a more focused journey, but I suspect most leaders will find value in all of the Small Things.

InfoQ: How can we read the room and get insight into people's moods?

Lopp: There is one move here and it takes a lot of practice. Sit down, don’t say a thing, and read the body language. Your brain is really good at discerning the disposition of a human from very little data. Who wants to be there? Who doesn’t? Who is ready for us to start? Who is distracted? Ok, now let’s apply what I know about each person to these observations. Phillip is distracted because his product planning process is on fire. Make sense.  We haven’t said a thing yet, and we’ve got the beginnings of an emotional map of the room.

Like I said, a lot of practice.

InfoQ: What's spidey-sense and how does it help to render decisions?

Lopp: Your brain is one of the best pattern-matching machines out there. This is both good news and bad news. The bad news, briefly, is that we tend to build patterns which match our lived experiences which makes many of us very biased to our experience and not experiences of others. That’s a different book.

The good news is that over time your pattern-matching can help you identify potential disasters earlier. Spidey-sense is your experience speaking loudly… unexpectedly. I use it a lot regarding employee job satisfaction. After many years, it’s really obvious to me in very subtle ways when a coworker isn’t happy with their role. It’s not always right, but its existence is more than enough reason to ask hard questions.

InfoQ: What mistakes do new leaders often make? Is there a way to prevent making them?

Lopp: All of them? Given leadership is a career restart, there are daily mistakes. The one I see the most with engineering leaders (but I suspect it applies to all leaders) is the tendency to regress when the stakes are highest. It’s when a new manager thinks he or she is helping during crunch time by helping finish the feature, fixing bugs, or otherwise regressing to their prior role because they think they are helping.

Let’s catalog the reasons they aren’t helping:

  1. They’ve put the team in a situation where they appear to be unable to complete the necessary work. Bad planning.
  2. They’re doing the work their team should do, so they’re sending unintentional signals to the team that they don’t believe the team can do the work. Bad signal.
  3. They’re not giving the team the chance to rise to the occasion. To figure out a creative means to complete the work. This might be impossible because of bad planning, but assume it’s not. What does the team think when the leader keeps saving the day by fixing bugs? It’s a safety net, sure, but it’s a net that isn’t allowing others to grow.

Leaders often rationalize this behavior as “I want to remain technical.” I want engineering leaders to be deeply technical, too. They should understand how a product, technology, or service works, but if that comfort of understanding comes from doing the engineering work, then… go be an engineer. It’s a great gig.

InfoQ: In the book, you suggest to delegate until it hurts. Can you elaborate?

Lopp: Often as a new leader, projects will show up that you know you can just crush because you’ve done them before. You know exactly how to get it done. Great, you can deliver solid business value by completing this effort, but how’d you get that experience? How many times did you fail before this type of project was easy for you?

Leaders need to give much of the work they might love to do to their teams so the team has the opportunity to learn. It feels counter-productive in a business setting because it’s likely very important this project goes well, but let’s say it only goes “ok” when you delegate to folks who have never done it before, but remember the other value created by this leadership act:

  1. You demonstrated trust and respect by delegating.
  2. They had a chance to learn.
  3. You had a chance to teach and coach them.

Even without perfect project results, I’d argue that because the leader delegated, they created more long term value for the company.

InfoQ: What are the conditions for managers to have regular staff meetings next to 1:1 meetings?

Lopp: I’d say that the moment that you have more than three direct reports you should consider a staff meeting. Why? You’ve moved from being a loose affiliation of humans to actually being a team and spending time each week together is the first small step in acting like one. 

InfoQ: What's your advice for conducting distributed meetings?

Lopp: Here’s three pieces of starting advice: 

  1. Make eye contact. Stare at them, not yourself.
  2. Collaboratively build an agenda beforehand, ideally in a Slack channel dedicated to that purpose. Follow that agenda.
  3. Look hard for the cues when someone wants to speak. This is more difficult in our video conferencing world now, but think how much more difficult it is for someone who already found it hard to get a word in edgewise in a normal meeting situation.

InfoQ: What's anti-flow, why do we need it, and how can we foster it?

Lopp: Flow is a common term for that state of mind when you’re building productively. You’ve got the entire problem in your head and you’re able to make progress on the problem effortlessly. It’s a tricky state that is as hard to achieve as it is to maintain.

Anti-flow is a similar state, except rather than directed and productive purpose, you achieve directionless creativity. It is weaponized shower thoughts. I foster it by getting on my bike for long rides where I can’t be interrupted by anything. I just let my mind wander and I often find novel next steps as well as new ideas. 

InfoQ: You mentioned in the book that "leadership is a set of principles that you mostly follow". How does this work, and how can this help us to improve our leadership skills?

Lopp: Each leader has a set of leadership principles they believe in. Here are two for me: I think that humans should be treated with respect. I believe transparency, even when it’s uncomfortable, is always the right move with the team. Your principles are different, but I think it’s important to reflect and document those principles and make them real. Seeing the principles in front of you gives you direction, a north star, when the job is the hardest. 

InfoQ: What's your advice to engineers who are promoted to management?

Lopp: Start by understanding that this new role is a career restart. That which made you a great engineer doesn’t necessarily make you a great leader. Ask for help from those leaders you admire. Admit when you are wrong. Learn from those failures. They will be frequent. Listen hard to alternative perspectives. Learn to regularly give consistent feedback. And remain calm when everyone is screaming. 

About the Book Author

Michael Lopp is a veteran Silicon Valley-based engineering leader who builds both people and products at historic companies such as Slack, Borland, Netscape, Palantir, Pinterest, and Apple. When he’s not deeply worrying about staying relevant, he writes about pens, bridges, humans, and leadership at the popular weblog, Rands in Repose. He currently works at Apple. This is the way.

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