Teach Strategic Thinking With 3 Simple Questions

Teach Strategic Thinking With 3 Simple Questions

When the Big Strategic Idea someone pitches you is blatantly boneheaded and un-strategic, you might remind yourself that strategic thinkers are made, not born. If this person is your friend or subordinate, then maybe it’s your job to help them learn the skill called “strategic thinking.” These three simple questions will get you off to a good start.

First: “What’s the point here?”

Like the guy who interrupts a meandering meeting with, “What are we trying to accomplish today?” you can awaken your mentee by probing for the point of a proposal. What result, end-point, outcome, or effect are they angling for?

Imagine that a manager has come to her boss with a plan to merge two departments.

“Boss,” she says, “I think we could capture some real synergies if we merged Madge’s department with Larry’s. I’ve got a plan for doing that, and I’d like to walk you through it and see what you think.”

But her plan isn’t the first thing to care about. The first issue to tackle is: how will the world be different if the plan is successful? Or, simply, “What’s the point here?” For instance, can she identify the “synergies” she’s promising?

We see friends’ calendars fill with speaking engagements. Occasionally we’ll ask, “Why are you talking to that particular group?” Often we’re told that it’s “good exposure,” or it’s an opportunity to “deliver a message.” If we’re feeling a little bold, we’ll press the point: Sure. But after the exposure, and after delivering the message, what do you hope your audience will say or do differently than before they heard your message? In other words, what’s the point here?

This question benefits effort at all levels of the organization. In fact, we’ve found that the bigger and more expensive the undertaking, the more likely this niggling little question has been ignored, or not answered thoughtfully.

Second: “What’s the point of the point?”

Now that we’re talking outcomes, not effort, the student of strategic thinking needs to examine how a proposed result fits into a bigger picture. “Sometimes it’s better to climb up than to drill down,” a wise admiral once told us.

So if you’re the boss, it’s not unfair for you to ask, “Okay, so how will this help me accomplish my goals?” It may be the first time they’ve pondered their contribution to your goals. And even better might be to ask, “How will that help me accomplish my boss’ goals?” That question moves their thinking up two levels, instead of just one.

Let’s say that the proposal to merge two departments could yield an interesting result: 25% reduction in cycle time of a key transaction. Great. But is the overall organization prepared to exploit faster transactions? Maybe the paperwork pileup would just drop down to another bottleneck, helping nobody’s higher goal. Or maybe it’s exactly what’s needed to goose along an important, higher-order achievement.

In any case, the so-what of the so-what is always a useful conversation, and helps people see their work through more strategic eyes.

Third: “What could go wrong?”

This is the part where you help your mentee develop strategic peripheral vision: teach them to anticipate negative side effects. Almost any strategic outcome risks negative side effects.

Sure, lots of side effects aren’t knowable in advance. But most forehead-slapping failures stem from easily predictable side effects that weren’t predicted. And that’s because nobody asked, “What could go wrong?”

In our little merger example, it would be easy to accidentally chase off talented employees. Or, maybe that “more efficient” system is also a more fragile one, easily broken by the absence of an employee or two. Or . . . lots of other things.

“What could go wrong” is the simple question that might have complex answers. But time and again we’ve seen that question raise our clients’ strategic thinking as they broadened their vision.

There are more than a few rocks to kick over in this conversation. The achievement itself can have side effects, but so too can the effort to produce the achievement. Also, side effects can occur immediately, and they can occur over time. Side effects can be second order, but also third order, and up. And they can occur in many, many domains: safety, politics (internal and external), costs, morale, and on and on.

There’s plenty to talk about. But the broader goal here is not to kill strategic ideas; it’s to make sure the ideas are fully fleshed out. It’s about ensuring that victories aren't Pyrrhic.


“Strategic thinking” – in fact, wisdom – occurs only in light of broad context. Understanding the point of our intentions, and then the point of that, and then being alert to repercussions: not a bad beginning down that path.

Published: June 1, 2015


    • Very nicely said. I enjoyed reading your article. Very interesting ideas you have here


    • Jason Lewis

      Bill and Wendi, I love the emphasis on the teachability of Strategic Thinking. So many managers get told they aren’t thinking strategically enough but no one teaches them how.

      And, the questions are super-powerful, I’ll be using “What’s the point of the point?” in my next coaching conversation.

      What can you share about asking these questions in a group setting?

      Thanks for giving me something steal-able!


    • Jason, thanks for the kind words! In some ways, the questions may work even better in a group setting. By brainstorming answers to the questions, the group teaches each other to think strategically. You (meeting leader or facilitator), then, can lean almost entire questions that direct without telling. Contrariwise, in one-on-one sessions, you may need to do a bit of telling — depending on the person.


  1. Bill and Wendi – lots to like about this post. I like “teaching with questions” – the socratic method. And the first question focuses on the “why” which is a great place to start. The last question can prevent a host of problems if it’s well thought out.


  2. Natalie Roemer

    Nicely said!


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