Strategy & Looking Like an Idiot

Raise your hand if you don’t know what the heck you’re doing at work. 

If we’re honest, that’s probably most of us. 

Now raise your hand if you’ve ever told someone who impacts your performance rating or compensation that you don’t know what the heck you’re doing.

That’s probably none of us. 

I recently created a list of impediments to effective strategy in organizations, and I realized that most of the items on the list reflect these paradoxes: 

1. No one really knows what they’re doing, and we’re wrong all the time, but every fiber of our being tells us to never admit that fact. 

2. To do strategy well, you have to act like an idiot—i.e., charge ahead even though you have no clue what’s ahead, and constantly change where you’re proven wrong.   

To understand those paradoxes, it’s important to state what effective strategy looks like. For me, good strategy is a creative effort that entails:

• defining an attractive destination and an educated guess about the best route to get there, 

• having a clear logic for those guesses, 

• learning and refining the guesses as things change in the world, 

• prioritizing effort and resources on the highest-impact and reinforcing activities, and

• generating alignment—emotionally and intellectually—among all the humans that need to carry it out.

With that definition, it’s easy to see how our reluctance to admit that we don’t really know what we’re doing gets in the way of effective strategy.

For starters, we don’t talk in the language of guesses—only plans. Imagine being at a wedding and hearing the groom say, “Based on my current hypotheses, I’m pretty sure marriage is the best option to pursue right now, but I intend on making adjustments as I learn more.” No one would have faith in that! 

Instead, we make clear public declarations in our vows. And having made those public commitments, we zealously protect any inkling that our marriage is anything less than perfect. 

So it goes in organizations. The best strategies are educated guesses, since no one knows the future. However, to look like we’re smart and look like we know what we’re doing, we’re more likely to create and communicate firm plans. Like Nostradamus with an MBA, we describe our  precise vision to everyone in the room, telling them just  how the future will unfold. 

We’re even more susceptible to having unreasonable certainty when we need to pitch a bold and confident vision for the future in order to secure funding. To the CFO, investment committee, or the foundation grantmaker, the “sure bet” strategic plan is way more attractive than the plan that is communicated as “we’ll figure things out as we go.” That happens, in part, because we know that those decision-makers also want to avoid looking dumb to their stakeholders. 

In the book Rework, Jason Fried and David Heinemeier Hansson describe how creating a plan can limit us: “When you turn guesses into plans, you enter a danger zone. Plans let the past drive the future. They put blinders on you. ‘This is where we’re going because, well, that’s where we said we were going.’ And that’s the problem: Plans are inconsistent with improvisation.”

But the problem is even worse: To truly improvise—to learn and adjust based on changing conditions—we need to tell the very same people we pitched the plan to some version of, “You know that thing I told you before? Well, I was wrong.”  

That’s hard to do because we’re fearful of looking like an idiot to other people, and especially to those who are in a place to judge and to affect our futures.  

In The Fearless Organization, Harvard professor Amy Edmondson describes this in more articulate terms: “Whether explicitly or implicitly, when you're at work, you're being evaluated. In a formal sense, someone higher up in the hierarchy is probably tasked with assessing your performance. But informally, peers and subordinates are sizing you up all the time. Our image is perpetually at risk. At any moment, we might come across as ignorant, incompetent, or intrusive, if we do such things as ask questions, admit mistakes, offer ideas, or criticize a plan.”

In my experience, this means that people rarely volunteer that their projects aren’t effective (because that implies that they’re not effective).

It often also means that people are biased in their analysis—what’s going well is attributed to their amazing skills, and what’s going poorly is attributed to external, uncontrollable factors. It’s only a small exaggeration to estimate that most of the leaders I’ve worked with can spot 100 impediments to success in the environment and in other people before they come to even one impediment that emanates from themselves.

Either way, these behaviors make it harder for organizations to be great at strategy because they inhibit learning—i.e., slow the process of making educated guesses even smarter. 

This problem is worse in organizations and teams with low psychological safety, but we bring our self-protective instincts with us to the workplace. Edmondson writes that “most of us want to look smart, capable, or helpful in the eyes of others. No matter what our line of work, status, or gender, all of us learn how to manage interpersonal risk relatively early in life.”

You might be thinking, “But what if we create robust routines that require us to stare at the cold, hard facts and reckon with this? Surely, that would help us have a dynamic strategy.”

Well, as much as we don’t want to look like idiots, we also don’t want to make others look like idiots. The result is that groups can develop what Chris Argyris, the late professor of organizational behavior at Harvard, called defensive routines—things like being silent in the face of bad ideas, sending mixed messages to shroud our actual thoughts, focusing on the easy-to-solve symptom rather than the root cause, and ignoring the elephant(s) in the room.

Here too, the instincts are in us long before we come to the workplace. In Strategy, Change, and Defensive Routines, Argyris writes: “The reason these defensive routines are not seen as counterproductive is that they are connected with caring, thoughtfulness, and effectiveness. We believe this because the routines are culturally taught to all of us early in life. We have been taught long before we joined organizations that these defensive routines are signs of mature behavior.”

Finally, the need to protect our status manifests in another way—we need to protect our territory and resources. 

In an organization that’s highly strategic, there would be a continual prioritization of activities and movement of people and financial resources to those activities that are most impactful. But this is not what happens in most organizations. 

Rather, it’s not what happens at the enterprise level. The executive director of a nonprofit described to me recently that his local office leaders regularly shift their staff around to the most promising projects, but no one ever applies this logic to the organization as a whole. The leader of Region A never says, “If the work in Region B is most important right now, we should move some of my team members to those projects.”

I suspect that happens because these leaders know that once they give up resources, they’re left with less power and less status, which of course is an outcome most abhor. 

One of my coaching clients did just that—she “temporarily donated” a couple of people on her team to a high-priority project led by someone else. A colleague of hers said that even though it was the right move for the organization, “It made her look weak. I think she learned not to do that again.”

Most organizations I’ve worked with just don’t have good mechanisms for reallocating talent between projects. But perhaps more importantly, they lack the ability to make these shifts in a way that preserves people’s status. 

What this means is that leaders don’t proactively solve for the organization’s needs as a whole and nominate their projects for elimination. And for that reason, strategy shifts are usually imposed with clear winners and losers.

Leaders often complain about other people’s unwillingness to change, but it seems pretty natural to resist change that’s done to us, which both disadvantages and reinforces that others have power over us.

In the Harvard Business Review article “Rethinking the Decision Factory,” Roger Martin argues that the lack of an effective reallocation mechanism leads businesses to a cycle of over-hiring and layoffs. And it’s a particularly acute problem for nonprofits because new initiatives must usually come from existing resources.

Is there a solution?

Heck if I know. I’m an idiot. :)

But these dynamics underscore that strategy is both an intellectual and emotional pursuit. These natural human emotions are impediments to effective strategy because they’re impediments to honest and logical reasoning. 

In planning processes, I’ve seen leaders acknowledge these dynamics, but still  choose to focus on the “right answer” in the moment, leaving the “culture stuff” for later. That’s a reasonable choice, but it may ultimately be shortsighted. 

It starts with a realization that an organization can have a great strategy, but it will never be great at strategy unless people feel comfortable with looking like idiots. 

Because creating that kind of culture requires us to behave counter to our learned instincts, it takes time to build. So, while it may be a distraction today, investing in building effective team dynamics and psychological safety is an investment in future strategy.