Be Encouraged

Development as a Leader

Not long ago, a colleague and I got into one of those conversations that starts casually and turns into something you’re still thinking and talking about days later.

The question was simple: if you could recommend only five books every leader should read, what would they be?

We went back and forth for a while. There was a flurry of activity on the dry-erase board in my office. Some titles were easy. Others sparked debate. We landed on four that we both felt strongly about.

Start With Why by Simon Sinek. If you don’t understand your own why, you can’t lead others toward theirs.

The Next Conversation by Jefferson Fisher. We’ve already talked about this one. Clear, direct, practical. Every leader needs it.

Dare to Lead by Brené Brown. Courage, vulnerability, and the kind of leadership that actually builds trust. It’s not soft. It’s hard.

The Five Dysfunctions of a Team by Patrick Lencioni. If you lead a team, this book will show you exactly where the cracks are and what to do about them… and yes, I’ve been accused of being a Lencioni fanboy.

Four books. Strong list. We were confident.

The fifth title…more on that in a moment.

Leaders Are Learners

Here’s something that genuinely surprises me: not every leader sees development as part of the job, or even considers it.

I don’t mean that as a criticism. I mean it as an observation. I’m genuinely shocked when I hear this perspective. Some leaders reach a certain level, figure the skills that got them there are good enough, they look around, and decide they’ve arrived. They know what they know. They’ve earned their seat. And the idea of continuing to learn, to grow, to have their thinking challenged, it feels optional. Maybe even unnecessary.

That mindset is one of the most dangerous places a leader can land.

John Wooden, one of the greatest coaches in the history of sport, said it simply: “It’s what you learn after you know it all that counts.”

Wooden wasn’t just talking about basketball. He was talking about the leader who stops asking questions…the leader who relies on what worked before and assumes it will keep working… The Fosbury who continues to rely on the Scissor Kick to get over the bar. The one who has quietly, without realizing it, stopped growing. I’ve shared in other posts the phrase I learned, “Win or lose, review the tape.” There is always room to develop, grow, and learn, regardless of where you are in your life and/or career.

Development isn’t a phase of leadership. It’s a requirement of it. Not because someone told you to. Because the role demands it and the people you serve deserve it.

The Slow Leak

Early in this series, we talked about “good enough” being a slow leak.

It’s worth coming back to that idea here because development is where the leak either gets fixed or gets ignored.

When a leader stops growing, the gap between what the role requires and what they’re capable of doesn’t announce itself. It doesn’t show up as a crisis on a Tuesday morning. It grows quietly. Slowly. Until one day, the job has moved forward, and the leader is still standing in the same place they were two years ago, wondering why things feel harder than they used to.

What got you here will not keep you moving forward. The skills, instincts, and approaches that carried you to where you are today are a foundation, not a finish line. The bar keeps rising. The approach has to keep changing.

That’s not a warning. It’s an invitation.

Development Looks Like Something

Here’s where I want to get practical, because “leaders are learners” is easy to agree with and easy to ignore.

The default move on development is passive. We wait for the training to be scheduled. We read when we have time, which means we rarely read. We login and “watch” the webinar, but we’re not really there. We turn the camera off and continue multitasking, which never really works anyway, and an hour later, we’re surprised the training is over, and we’ve learned almost nothing. We say we want to grow, and then fill every margin of our day with busyness that feels productive but doesn’t move us forward. We rely on experience as a substitute for learning, as if doing the same thing longer automatically makes us better at it.

It doesn’t.

The stronger move is to make development intentional. Not a someday. A practice.

We don’t have a content problem. Books, podcasts, TED Talks, HBR articles, YouTube channels, newsletters. The volume of leadership development content available to us today is staggering. You could spend the rest of your career consuming it and never run out. We have an intentionality and discipline problem. The content is there. The question is whether we show up for it consistently.

Start with the basics. Read consistently, not occasionally. And reading’s close cousins (podcasts, articles, talks) counts too. Even small doses of intentional learning compound over time into something significant.

Then get outside your own perspective. Find people who think differently than you and stay in conversation with them. Seek feedback that is honest, not just comfortable. The people around you know things about your leadership that you don’t, and your blind spots don’t disappear on their own. Creating space for both is a development move.

And then do something with what you’re learning. Apply it. A book you read and filed away did less for you than a single idea you actually tried. Reading 10 books in a year is just expanding knowledge, unless you are growing and improving from what you learned.

Stephen Covey said it plainly: “The key is not to prioritize what’s on your schedule, but to schedule your priorities.” Development doesn’t happen in the margins. It happens when you decide it matters enough to protect time for it.

Your Turn

Before your next week begins, here’s what I’d ask you to consider:

What is the last thing you learned that actually changed how you lead? Not a concept you found interesting. Something that changed your behavior, your approach, your thinking.

If you have to think about it for a while, that might be the most useful data point you get from this entire series.

Development isn’t about having all the answers. It’s about staying curious enough to keep finding better ones.

About That Fifth Book

You may have noticed we only listed four titles earlier. Not five.

That was intentional…sort of.

Because we’re still working on it. Still debating. Still learning. Still reading new books. Which, come to think of it, is kind of the point.

We had a list of strong candidates we kept circling back to. Titles like Good to Great by Jim Collins. Atomic Habits by James Clear. The 4 Disciplines of Execution by McChesney and Covey. Measure What Matters by John Doerr. The Goal by Eli Goldratt. The 21 Irrefutable Laws of Leadership by John Maxwell.

All good. All worth reading.

So we left it open…for now.

And now I’m asking you: what would you put on the list? What book has had the most impact on how you lead? What title would you hand to every leader you know?

Drop it in the comments. I’m genuinely curious, and we might just find our fifth book.

Be Encouraged.

This is Part 4 of a series on Becoming Good at Growth. If you missed earlier posts, you can find them here: Part 1, Part 2, Part 3. Next up: the wrap-up, where we pull it all together.