My Favorite Facilitation Books ✍🏻 Drawn to Leadership

Three facilitation books every tech leader should read

Say you're a CTO, a product manager, or a tech lead. Or any other type of leader - formal or informal. You realize that your company's meeting culture is holding you back. So you decided to do something about it.

René Brown once said that another word for leader is facilitator. Facilitation comes from the Latin word for easy. And as leaders, we need to make it easy to work together.

I'm not a professional facilitator. I’m working as a Head of Engineering, as a manager like most of you. But my impatience with bad meetings is driving me to learn about facilitation. It's a way for me to channel my impatience with bad meetings into something healthy.

Facilitation means structuring meetings so that there is more personal connection, more collaboration, and more decision-making.

So if you, like me, are running out of patience with bad meetings, here are my picks for the best writings on facilitation: three evergreen books that have helped me improve meeting culture by becoming a better facilitator.

Facilitator's Guide to Participatory Decision-Making by Sam Kaner 🎯

In my early days as an iOS Team Lead, I quickly realized that people despise being told what to do. Yes, leadership is about vision and direction. But people want to be involved in how you get there. And as a leader, you need the buy-in of the team that's part of implementing change.

The Facilitator's Guide to Participatory Decision-Making was a revelation. It taught me the dynamics of decision making in a group, how to get agreement without being blocked, and how to increase the stickiness of decisions. I've been using the methods in this book in my work for over 10 years. For example, we used the scale of agreement to make decisions in the iOS team when we were planning a major architectural change.

This is one of the few books I own in print despite my preference for e-books. This is because for a long time, there was no electronic version of this book. Now there is, but the book is designed as a workbook. So it's probably worth buying the paperback version anyway.

Key takeaway: The "Diamond of Participation" from Sam Kaner's book illustrates how groups move through phases of divergent thinking, a challenging "Groan Zone," and convergent thinking during collaborative decision-making. Divergent thinking expands ideas and perspectives, the Groan Zone processes complexity and conflicting viewpoints, and convergent thinking narrows the focus to build consensus. Effective facilitation ensures that all voices are heard, complexity is managed, and the group arrives at well-supported decisions.

The Art of Gathering by Priya Parker 🎨

Looking back on all the bad meetings I've been to in my career, I've thought once or twice that maybe we'd be better off not having meetings at all.

Are all meetings bad? Of course not. We need meetings to work together, we need meetings to solve problems, we need meetings to make decisions. But if we are going to have a lot of meetings, we had better be good at them.

The Art of Gathering emphasises the importance of designing gatherings with intention and clear purpose. It challenges conventional hosting norms and encourages bold choices in guest selection, ritual and facilitation to foster connection and engagement. Through practical advice and stories, Parker shows how purposeful gatherings can create meaningful experiences.

It's not a book specifically about work meetings. But it's a book anyone who organises work meetings should read.

Key takeaway: In Chapter 1 of The Art of Gathering, Priya Parker emphasizes the importance of defining a clear and specific purpose for any gathering. Instead of defaulting to traditional formats or vague objectives, hosts should ask themselves why they are truly convening people and use that purpose to shape every aspect of the event. A well-defined purpose creates meaningful, intentional gatherings that resonate with participants and achieve their goals.

The Secrets of Facilitation by Michael Wilkinson 👻

If this book were a YouTube video, the title would be "134 ways to improve your meetings (Do this now!)". But this time the content of the video would live up to the clickbaity title.

The Secrets of Facilitation provides facilitators with practical tools to achieve consistent, repeatable results with groups. Covering essential skills such as effective questioning, decision-making and managing group dynamics, the book provides step-by-step guidance for both novice and experienced facilitators.

It's part of the canon because sometimes I don't want to deduce everything from first principles. Sometimes, I prefer to be told what works.

Key takeway: In Chapter II of The Secrets of Facilitation, Michael Wilkinson emphasizes the importance of the "starting question," which sets the tone and direction of a facilitation session. He explains the structure of so-called Type B questions to stimulate creative thinking and the exploration of new ideas. Asking the right starting question in a meeting will lead to a lively discussion from the start.