Reconsidering Strategic Thinking

Sarah B. Drummond
4 min readJul 15, 2022


I am writing my ‘blog this week from heaven. And I don’t say that because I’m on Cape Cod, and the weather has been outstanding, although both those statements are true. Nor do I write “I’m in heaven” because I’m spending time with the people I’d be happy to hang out with for all eternity.

I am taking a class this week. It’s a class on leadership where all I have to do is engage and learn. I oscillate between overwhelming gratitude and feeling like I’m getting away with something.

Art Kleiner is teaching a course at the Cape Cod Institute on how change leaders can listen to their wise inner advocate. Many of my minister friends have asked if the Cape Cod Institute is the same thing as Craigville, but it’s not. My colleague who recommended we check out this course said that the reason I’d never heard of the Cape Cod Institute before this summer was because it attracts a “special kind of nerd.” I now know the truth: I am a special kind of nerd. Suffice it to say, I’ll be back.

The workshop with Kleiner is giving me permission to think and talk about strategic leadership. Why do I need that permission? Don’t I do that every day? Well, yes, but I have to pretend it’s something else. Strategic people are easily categorized as manipulators. They use people and operate from a base of selfish ulterior motives. They’re not theologically or intellectually… deep.

Kleiner, a respected leadership coach, is turning my negative associations with strategic leaders on their ear. For instance, he doesn’t mind when we go into problem-solving mode; he encourages it. He knows that getting things done isn’t just a nice-to-have kind of leadership practice. He’s teaching me that some of the behaviors religious leaders often associate with broods of vipers are actually superpowers when used carefully and intentionally.

The biggie for me today: “mentalizing.” Kleiner had to work hard to get through to me on what mentalizing is. It’s not empathy, and it’s not conscientiousness. It’s the capacity human beings have for figuring out what other people are thinking and satisfying them without them having to ask us to. For years, I’ve been told, “What other people think doesn’t matter.” But I’ve never been able not to care. Kleiner has now given me provisional permission.

Why provisional? Because mentalizing is a skill we need to learn to turn on… and turn off. Obsessing about what others think will lead us to ineffective leadership because all we’ll ever get to is problem-solving, never the strategic thinking that comes from pulling back from individual wants and looking at what’s in the best interest of the whole.

Like every leadership practice, mentalizing has a shadow side. We all have to mentalize when we’re low-down on the food chain, as we can only succeed by figuring out what those who have power want from us and giving it to them. As we advance in power and authority, we need to mentalize less, so we stop doing it. Then, we become less competent at motivating people, as we don’t understand what makes them tick. We once knew how to read others, and we’ve forgotten.

Kleiner calls this phenomenon, which one might consider perspicacity’s Peter Principle, the “mentalizer’s paradox.” I call it every power relationship I’ve ever had, where those who are above me in the hierarchy don’t know a thing about me, whether they realize it or not. Then, when I get a crack at being in power, I make clueless mistakes, thinking I “get it” when I don’t.

As I prepare for my last day of class tomorrow, here are two lessons I hope never to forget:

  1. Continuing education for leaders is the difference between rote action and thoughtful strategy, and rote action isn’t what our communities need from us today. Whatever might be our habits now are, I can guarantee, outdated. It takes a while for habits to become rote, and change is happening at breakneck speed; do the math.
  2. There’s nothing unfaithful about strategic leadership. If we are to be good stewards of the resources we control, and the power that’s been delegated to us, we ought not squander our energies on that which doesn’t work.

In the summertime, we all need rest. I’m starting to learn that rest and renewal only change me when I’m also replenished. We’ve all given so much of ourselves in these recent, isolated years. We do so as a Christian response to the love that’s been freely given to us by God. I want to be the kind of Christian that can empty myself and trust God to fill me. Sometimes that works best when new ideas displace old habits, and I find those who can help me put new wine into new wineskins.

Strategic leadership, smiled on in the business world but often viewed with suspicion from religious communities, is something we need to learn to employ even in choosing how to get the rest, renewal, and replenishment we need. These times are simply too complicated to approach how we’ll use the gifts God has given us without employing our God-given, utterly learnable, strategic minds.



Sarah B. Drummond

Sarah Birmingham Drummond is Founding Dean of Andover Newton Seminary at Yale Divinity School and teaches and writes on the topic of ministerial leadership.