The Strategic Question



You know how there’s some work that you do that you absolutely love? It’s the work that absorbs you and excites you. It’s not just that the work is making a difference and having an impact; it’s that the work means something to you. Frankly, this is the work that, when you signed up for this job, you hoped you’d be doing. And then there’s all that other work you’ve got to get through. At Box of Crayons, we make the distinction between Good Work (the everyday, get-it-done, this-is-my-job-description type of work) and Great Work (the work with both more meaning and more impact), all with the goal of helping organizations and their people do less

"We’re slowly waking up to the fact that being busy is no measure of success."

Good Work and more Great Work. You can probably imagine how things might shift if you and your team were all doing, say, 10 percent more Great Work. But quite frankly, who has the time? You’re already behind on emails, meetings, deliverables, exercise, reading and family time. You’re at full capacity. How could you possibly say Yes to anything more?


At the same time, perversely, in these hurly-burly days of endless connectivity, lean organizations and globalization, it’s de rigueur to humblebrag about being overcommitted and overwhelmed. “How are you doing?” they ask. “Busy,” you reply. “But a good busy.”

We’re slowly waking up to the fact that being busy is no measure of success. George Bernard Shaw was on to something years ago when one of his maxims for revolutionaries stated, “The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.” 4-Hour Workweek author Tim Ferriss drove the point home recently when he said, “Being busy is a form of laziness—lazy thinking and indiscriminate action.”


People have lots of snappy advice for you. “Work smarter, not harder.” “Be more strategic.” These maxims tend to be TBU: True But Useless sound bites that sound good but are impossible to act upon. In fact, “strategic” has become an overused quali er, something we add to anything that we want to sound more important, more useful, more thoughtful, more . . . good. This isn’t just a meeting. It’s a strategic meeting. A strategic report. A strategic lunch date. A strategic purchase of that fantastic pair of Jeffery West shoes I can’t really afford but have been admiring for a while.

It can all leave employees supremely indifferent to the idea of strategy. When you combine the overuse of the term with the fact that anything to do with strategy is often seen as being “their work”—when “they” are anyone two or three levels higher than the employees— well, you’re likely to encounter a nasty but predictable case of the SPOTS: Strategic Plans on Top Shelf.

But strategy isn’t a thick PowerPoint document gathering dust somewhere. It’s far more fundamental and common than that. Of the many de nitions of “strategy” that I’ve seen, I think I like Michael Porter’s best, when he said, “The essence of strategy is choosing what not to do.”


This question is more complex than it sounds, which accounts for its potential. To begin with, you’re asking people to be clear and committed to their Yes. Too often, we kinda sorta half-heartedly agree to something, or more likely, there’s a complete misunderstanding in the room as to what’s been agreed to. (Have you ever heard or uttered the phrase, “I never said I was going to do that!”? Me too.) So to ask, “Let’s be clear: What exactly are you saying Yes to?” brings the commitment out of the shadows. If you then ask, “What could being fully committed to this idea look like?” it brings things into even sharper, bolder focus.

But a Yes is nothing without the No that gives it boundaries and form. And in fact, you’re uncovering two types of No answers here—the No of omission and the No of commission. The rst type of No applies to the options that are automatically eliminated by your saying Yes. If you say Yes to this meeting, you’re saying No to something else that’s happening at the same time as the meeting. Understanding this kind of No helps you understand the implications of the decision.

The second type of No you’re uncovering—which will likely take the conversation another level deeper—is what you now need to say to make the Yes happen. It’s all too easy to shove another Yes into the bag of our overcommitted lives, hoping that in a Harry Potter magical sort of way it will somehow all be accommodated. This second type of No puts the spotlight on how to create the space and focus, energy and resources that you’ll need to truly do that Yes.

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