The Missing Ingredient of Being Strategic
Last week, I shared what AI tools noticed about my leadership philosophy. I asked them to do the same for my perspective on strategy.
What Claude Told Me
“Your strategy philosophy emphasizes that strategy is fundamentally about people, not analytics. You believe effective strategy requires leaders to be comfortable ‘looking like an idiot’—making educated guesses, admitting uncertainty, and learning continuously. Strategy must be scrappy and action-oriented, avoiding the trap of endless planning over doing. You stress that alignment comes from shared understanding of the ‘why,’ not just coordination of tactics. Strategic leadership means always-on sensing (talking to customers directly), making thinking visible to others, and creating inclusive routines where strategy happens daily—not annually. Most importantly, psychological safety enables the honest learning that makes organizations truly strategic, not just having a good plan on paper.”
Strategy Language Gets in the Way
Claude captured the philosophy, but one thing I continue to learn (or fail to anticipate, depending on how you think about it) is just how confusing the language of strategy is.
As someone who has worked in and studied strategy most of my career, the underlying concepts and terminology are intuitive. However, strategy is not contextually intuitive for everyone.
In fact, the language of strategy often obscures the fairly straightforward concepts it’s meant to describe.
We use terms like “competitive analysis” and “value proposition” rather than just asking questions like, Who buys from us, and what problems are they trying to solve when they do so?
We use terms like “strategic fit” and “coherence” rather than plainly asking, Are our activities consistent with each other? Does anything work at cross purposes?
We use terms like “strategic horizon” and argue over what’s a “short-term” strategy versus a “long-term” strategy, rather than asking, What’s going to deliver results next year, and what’s going to deliver results after that?
And the amount of energy organizations spend debating the difference between mission, vision, strategy, tactic, and objective could probably power a small village.
As with many parts of life, simplifying language and being direct is useful. This is especially important in a world in which organizations need everyone to act like a strategist.
The Missing Ingredient of Being Strategic
Working with executives over these five years has revealed something practical that enables all of this: buffers.
Some of the buffers are tactical planning interventions, like:
Assuming there will be an unexpected project that takes a meaningful portion of the team’s time and effort, even if you don’t know about it at the start of the month or quarter.
Categorizing projects into what’s truly required versus what’s aspirational (i.e., could be altered if needed).
Holding teamwide meeting times so there’s space to respond to unexpected events.
All of those interventions are about enabling a team to be agile and responsive, rather than stuck.
Another example of a buffer is scheduling more time than you need for team meetings. If the team meetings are too tightly scheduled, there’s almost always a rush to get through the agenda, creating an overly tactical team. There’s no space for impromptu strategic thinking. Things like:
That data is different from what we’ve seen previously. Is it time to change our approach?
I heard something similar. Are these one-off instances or a trend we need to address?
This same dynamic arises with our individual calendars. Without buffers—space between meetings and unallocated time on the calendar—people feel sped up and overwhelmed, preventing them from seeing important connections.
It’s not that people simply need to put “strategy time” on their calendars. It’s that they need a schedule that provides the felt sense that they can be creative and expansive. There's a reason why we have good ideas in the shower—it's one of the few forced moments of pause in modern life, where our minds can wander and make unexpected connections.
What’s Interesting to Me Now
As I reflect on most of the strategy efforts I’ve participated in, the unstated goal was to pick the right strategy. The assumption was often that (a) there was a right answer and (b) the organization was limited in how many things it could pursue.
However, as new technology tools drive down the cost of R&D by enabling both rapid prototyping and faster analytical cycles to know whether experiments are working, organizing a strategy process to land on a single, correct idea likely doesn’t fit the moment. Instead, the optimal strategy process probably looks much closer to “launch as many ideas as possible and see what works.”
Of course, this situation is not completely novel—the world has always been changing, and we’ll only know in hindsight whether this moment truly contained a faster rate of change than normal. As such, I suspect most of the technical implications for doing strategy in a dynamic environment are intensified versions of the familiar principles of agile strategy—i.e., shorter timelines, greater flexibility, and an emphasis on rapid learning and iteration.
What seems different about the moment, however, is how it challenges the role of the boss and strategist. If you’ve spent your whole life being praised and rewarded for getting to the right answer faster than others, what does it mean if you start the strategy process by admitting that you probably don’t have any better knowledge than others? What does it mean as the boss to give up your role as the oracle and to cede your power to determine the best path to data?
I suspect the leaders and organizations that thrive going forward will be those who can hold the tension between being humble enough to admit ignorance, confident enough to make bold moves when necessary, and secure enough to operate a system that feels constantly unmoored. That requires both intellectual shifts and emotional ones.