Nick Caldwell


FAQ: What books would you recommend for new managers, directors, and leaders?

My four favorite leadership books in no particular order

I get asked this question so often that I finally decided to write the answer down. Before we go any further: proceed with caution. Good leadership is contextual and you will learn it best from experience not books. The first thing I tell new engineering managers is that blindly following any SCRUM book you’ve read is the surest way to screw up your team. You’ve got to learn to take ideas from many places, contextualize, and apply them to your current situation.

These books are written by battle-tested leaders who have strong opinions on management methodologies. Each book played a key role in part of my own career but I don’t agree with everything in them. Instead, I’ve taken bits and pieces from each to fashion my own leadership style. I recommend you do the same!

Great book for people managers

Managing Humans

Michael Lopp

This is the first management book that really resonated with me and it was recommended by one of my direct reports a few months after he joined my team.

Why? Well, I was still a new manager back then and no one had yet told me that when it comes to leadership, people matter more than code. I suspect this book was a subtle hint that I needed to change my leadership game-plan.

Managing Humans is filled with stories from a manager’s perspective. While it’s a bit rose-colored, I believe it’s a fantastic introduction to all the coordination, stakeholder management, and empathy required to develop a people-oriented management style and healthy team.

“Ironically, the second most common complaint I’ve heard from frustrated employees is, “My manager has no idea what I do.” It’s good to know the problem goes both ways, no?”
 — Michael Lopp, Managing Humans
“My definition of a great manager is someone with whom you can make a connection no matter where you sit in the organization chart.” 
― Michael Lopp, Managing Humans
Hone your competitive edge


“Neutron” Jack Welch

Jack Welch is the patron saint of competitive leadership and Winning is all about developing your edge as a leader, spotting opportunities, and building teams that aggressively tackle goals.

Whereas Managing Humans is all about developing connections to people, Winning is just pure Old-Testament, kill or be killed, trench-warfare, law of the jungle stuff. Jack is famous for popularizing the concept of stack ranking and laying off more than 100 thousand people from General Electric in the 80’s. He’s also one of the most successful and influential CEOs of all time. Repeating my earlier warning: proceed with caution, this book is thought-provoking and has a great spirit, but it also has a few ideas that will wreck your team if used incorrectly.

By the middle of my career, when I’d become a manager-of-managers, I had developed a style that was perhaps too pivoted towards empathetic leadership. I love teams and people! But at the director level you have to “get off the floor” with your team and think about more about results. Winning was a wake-up call for me about the importance of disciplined execution, decision making, and developing top talent.

“Effective people know when to stop assessing and make a tough call, even without total information. Little is worse than a manager who can’t cut bait.” 
Jack Welch, Winning
“Leaders relentlessly upgrade their team, using every encounter as an opportunity to evaluate, coach, and build self-confidence.” 
Jack Welch, Winning
Organizational design

Thinking in Systems

Donella Meadows

This is a weird one, perhaps more of a philosophy book masquerading as a discussion of complex systems. I’m surprised more people haven’t read it though because it can be applied so broadly (perhaps that’s its fundamental flaw).

At any rate, Thinking in Systems is an amazing primer for organizational design, even though it doesn’t set out to be. I first read it when my organization size reached about 40 people and I could no longer “check-in” with every person on the team regularly. I wondered how to get my growing network of product teams to work well together. Subcultures were beginning to form, it got harder to communicate the mission, and other “big team problems” started to emerge. My team was also becoming more influential and needed to interact with more and more partner groups around Microsoft. I was struggling with understanding how my little team could influence an organization of several thousand people. As promised, this book changed my way of thinking and I could be heard quoting from it for several weeks after reading.

“Let’s face it, the universe is messy. It is nonlinear, turbulent, and chaotic. It is dynamic. It spends its time in transient behavior on its way to somewhere else, not in mathematically neat equilibria. It self-organizes and evolves. It creates diversity, not uniformity. That’s what makes the world interesting, that’s what makes it beautiful, and that’s what makes it work.” 
― Donella H. Meadows, Thinking in Systems: A Primer
“Purposes are deduced from behavior, not from rhetoric or stated goals.” 
Donella H. Meadows, Thinking in Systems: A Primer
Best book on the market today

Radical Candor

Kim Scott

This book is so ridiculously chock full of good management advice, war stories, and re-usable frameworks that any attempt to summarize it will be a total fail. It is simply one of the best management books ever written.

Those who know me well know that I’m driven, direct, and not afraid to speak my mind. I’m also passionate about people. In an era governed by political correctness, participation trophies, and consensus-driven decision making, this book stands out for its ability to balance empathy and candor. It will teach you how to build trust, attack goals instead of people, avoid acceptance of mediocrity, and more.

Perhaps the only flaw is that is written in a way that reminds me of Rich Dad Poor Dad or Strength Finders, books with an ulterior motive of selling more books, training courses, etc. It can be a turn off at times, but this is without a doubt the best management book you can read today.

“When bosses are too invested in everyone getting along they also fail to encourage the people on their team to criticize one another other for fear of sowing discord. They create the kind of work environment where being “nice” is prioritized at the expense of critiquing and therefore improving actual performance.” 
Kim Scott, Radical Candor

rock on

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