The Art of Leadership, by Michael Lopp

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I have been reading Michael Lopp’s blog, Rands in Repose, for fourteen years, and liked his previous books, so I bought and read this newest book immediately upon release as it’s especially relevant to my work as an executive coach. Lopp shares what he has learned as a manager at Netscape, a director at Apple and most recently as an executive at Slack, and distills those learnings into 30 leadership practices (split roughly evenly between manager, director, and executive sections) that he describes in a few pages each. As he writes in the intro,

“This is a book of repeatable practices that over time will combine to form sustainable, self-improving leadership. Pick a small thing, practice it for three months, and discover for yourself how it will make you a better leader.”

What I like about this book is that these practices are described and grounded in typical stories that I have seen repeatedly in technology companies. Lopp’s chapters start with a situation and how it goes wrong, and then offers concrete and practical advice on how he has learned to handle it, down to sharing how he manages his time and runs staff meetings. I appreciate the experience and wisdom embodied in these practices; the book translates “The Art of Leadership” into its subtitle of “Small Things, Done Well”.

Even though many of the chapters are updated blog posts, packaging this content into a book provides more coherence, as well as a narrative tracing how his focus and thinking evolved as he ascended the leadership ranks, from doing the work as an engineer, to empowering the team to do the work as a manager, to delegation and communication as a director, and to vision and culture as an executive. Each of these transitions is a phase shift in that “What got you here won’t get you there” i.e. the traits and skills that made you successful at one level will work against you succeeding at the next level.

I also like the framework he shares in the afterword for leaders to reflect on how they are allocating their time and energy. He suggests estimating what percentage of time you spend on Vision, Strategy and Tactics currently, and where you’d ideally like to be as a leader. His definitions are:

  • Vision: Seeing an impossible objective, defining the broad strokes of how we might achieve it, and selling us on the idea
  • Strategy: Breaking down the vision into understandable chunks and defining the concrete steps we’ll need to take to meet the chunked individual goals.
  • Tactics: Unfailingly follow each step as described.

Even though he doesn’t state this explicitly, my sense is that a leader spends more time on Tactics as a manager, Strategy as a director, and Vision/Culture as an executive.

I’ll share a few of my favorite chapters from each section (with links to the corresponding blog posts when available) to illustrate how this evolution and framework show up in the practices he shares.

Manager:

  • Act Last, Read the Room, and Taste the Soup where he describes how his job as a manager is to “taste the soup” – not to tell his team how to do their jobs, but to ask “small, but critical questions based on legitimate experience [that create] an environment of helpful and instructive curiosity.”
  • Spidey Sense is “your experience speaking… loudly. A moment of inspiration. Of intuition. It feels like magic because the insight arrives instantly appears out of nowhere, and that’s why you should trust it.”
  • A Performance Question where he reminds managers that their job is “How do I make this human better?” not to manage performance. This means that a manager needs to “give yourself months and months to discuss a gap in performance. Analyze it from different angles and make it about learning.”

Notice how these posts share a theme of moving beyond your own technical knowledge and performance, towards the goal of maximizing your team’s performance. Many engineers struggle with this shift in mindset, leading to what he calls The New Manager Death Spiral, and Rands points out that building true trust with your team is the way to avoid that manager meltdown.

Director:

  • Delegate Until It Hurts, which does not seem to have an associated post, but the lesson is in the title. As Rands describes, a good manager is “giving away just about everything that lands on their plate to members of their team because their job isn’t building the product, their job is building a team that is capable of building the product.” This chapter is naturally followed by the chapter How to Recruit.
  • Say the Hard Thing: “Your goal in life is to make feedback in all directions no big deal. …All the constituent parts of the act of giving and receiving feedback provide an opportunity to build trust in a relationship.” This chapter is paired with Rainbows and Unicorns on the importance of genuine compliments, which he defines as “a selfless, timely, and well-articulated recognition of achievement”.

Notice that going from manager to director means that your job is no longer about getting the work done, but about empowering the managers of teams doing work by delegating and communicating effectively with them. It’s one more level of abstraction away from the technical work where people start their careers, and feels very fuzzy when you come from an engineering background, so I appreciated the concrete practices here to improve leadership at this level.

When I got this book, I went straight to the the Executive section, as that’s where I felt I had the most to learn from Lopp’s experience. This is where he focuses in on the practices he has developed around vision and culture:

  • How to Build a Rumor is a wonderful story on how to extract signal from the noise of a rumor in your org. “There is a reason this rumor exists. There was some situation in the past that forced its existence, and the only useful thing you can do is to stop and reflect on what truth is contained within its toxicity. … The rule for your team is, “In the absence of information, they will make up the worst possible version of the truth usually reflecting their worst fears.”” This is closely followed in the book by The Signal Network on how to develop higher signal sources of information.
  • The Culture Creek was a delightful allegory of how a leader can develop the culture of an organization by choosing which stories to reinforce. “A core set of humans in the building retold the stories that mattered to them, over and over again, slowly carving a well-defined path in the consciousness of the company. With time, it becomes religion.”
  • I was surprised and delighted to see that several chapters in the executive section were about “soft” topics:
    • A Precious Hour where he invests in himself by regularly blocking off an hour to build something
    • How to Rands – a guide to his idiosyncracies as a leader, showing his self-awareness
    • Find a Mentor, where he shares how his coach has been critical to his development as a leader (a message I approve of as a coach)
    • Be Unfailingly Kind – the capstone chapter summing up his leadership philosophy in a brief motto.

I really appreciated Lopp’s perspective on The Art of Leadership, as the concrete practices he recommends are clearly designed for leaders to handle common pitfalls as they take on more responsibility. I have been recommending this book to several of my coaching clients, and I think most leaders could benefit from reading it and adopting the practices they find relevant.

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