5 Books That Will Teach You Everything You Need to Know About Creative Leadership

Nobody gets into advertising to become a manager. But if you’re good at it, that’s where you end up.

Inevitably, your job moves from making things to nurturing your teams’ ideas, managing their careers, and taking the hits so they can do the work. It’s the hardest pivot in our business outside of landing your first job.

And the industry is terrible at preparing creatives for it. 

I struggled with this transition more than I’d like to admit. Watching other managers helped. The great ones showed me what to aim for and the bad ones showed me what to avoid. But osmosis has its limits. 

So I started reading. Dozens of leadership books later, these are the five I keep turning to.

1. Herding Tigers, by Todd Henry

This book is built for the moment when a creative pivots from being a maker to leading a team of other makers. Henry gets into this identity shift without making it feel like homework. It gave me a way to put words around my own leadership style, and you can’t lead with intention until you know what you stand for.

If you only read one book on this list, read this one. I buy a copy for any new CD on my team. 

2. Leaders Eat Last, by Simon Sinek

Once you understand your leadership style, this book will help you decode how to be a leader people want to follow.

Sinek gets into why people do their best work for leaders who protect them, and why they shut down around leaders who don’t. It made me view leadership as debt I owe my team. If you see me get in the food line last, now you know why.

3. Unreasonable Hospitality, by Will Guidara

This is not technically a leadership book, but it’s the best book I’ve read on service. Being in service of your team, clients, and collaborators is not a nice-to-have; it’s often the thing people remember. 

This book changed how I think about professional relationships and reminded me that personal touches matter. Your reputation is built on the stories people tell when you’re not in the room.

4. The Culture Code, by Daniel Coyle

Then there’s the room you’re asking everyone to work in. What kind of culture are you building? 

The Culture Code is about the small behaviors that make people feel like they can speak up, take risks, and be part of something. It taught me that culture is not a vibe, a deck, or calling yourselves a “family,” but the tiny stuff you do every day.

5. The Cubs Way, Tom Verducci

Finally, this book teaches you how to build a team that actually wins. 

Swap “ballplayers” for “creatives,” and a lot of it still holds: Know people’s strengths and weaknesses; put the right people on the right assignments; and remember that great work usually takes longer than anyone wants it to. This is the book I return to when a team looks good on paper, but still isn’t quite clicking.

No book will magically make you a great leader. But if you’re a creative person who just got handed the keys and no manual, these five will at least give you a start.