Hess: You’ve written several books on school leadership. How is this one different?
City: This book was the hardest to write—I’ve never revised so much in my life! All my books aim to take complex ideas and retain that complexity while making them accessible enough to help educators make improvements. Most focus on concrete practices and processes—doing instructional rounds, using data, holding meetings, developing a strategy—but this one attempts to do something much more amorphous: explain how to be a leader. How do we make explicit what it is that effective leaders do, often intuitively, and what trips them up? For example, when I was a principal in North Carolina, I prioritized facilitating professional learning and avoided anything that felt too conflict-laden, which I justified to myself as my being focused on kids. I was naïve about some of the forces around me that mattered for kids and teachers to be successful. This book would have helped me understand all that.
Hess: So, just what does it mean to “lead strategically”?
City: At its heart, leading strategically is about anchoring in purpose; making choices about what to do, not do, and how; and then learning as you go. You can have great urgency, but that doesn’t mean you should play Whac-a-Mole with everything coming at you or that your calendar should be packed with meetings. Leading strategically is also about getting comfortable with uncertainty, embracing the fact that multiple things can be true at once, and recognizing that we’ll make more progress if we help those around us become more strategic, too.
Hess: What’s your response to readers who are skeptical of one more book about leadership?
City: Skepticism is one way of being strategic! It means you’re asking, “Why this thing? How is it going to help with something that matters?” Here’s the case I’d make: If you find yourself not making as much progress as you want, this book can help you figure out why that might be and what to do about it. If you’re in a role where it feels like much is beyond your sphere of control, this book can help you find and exercise your agency. If you feel like you are quite strategic yourself, but the people around you aren’t yet, this book can help you figure out how to build others’ capacity. What gives me the most confidence that this book is useful is that educators in a range of roles have told us so.
Hess: You write that there are five elements to strategic leadership. Can you talk a bit about what they are?
City: The five elements are: discern; cultivate relationships; understand context and history; harness power; and think big, act small, learn fast. Each element on its own can make you more strategic, but together they help you sift through the noise, identify what matters most in the moment, and assess the implications of that for yourself and your organization. The great thing is that you can develop these elements in yourself and others. For example, harnessing power has long been my biggest area for growth as a leader, but I’ve gotten better over the years.
Hess: Early on, you discuss some common dilemmas that school leaders encounter in their daily work. What are a few of these, and how does your approach help with them?
City: There are so many common dilemmas! The long lists where everything, and thus nothing, is a priority. Confusing the means and the end, like focusing on using data while forgetting why it’s being used. Designing high-potential work without including the people who are impacted by it, those who are needed to implement it, or those who could jeopardize it.
Our approach is designed to help with these sorts of dilemmas by considering the human elements of change while thinking systemically about how the parts relate. How do you filter the noise while staying committed to a North Star? How do you take intentional action, learn, and adjust? What are the right questions to ask? How do you get curious, listen well, and get out of your own way?
