Stop Overthinking Your Strategy

How small companies can reframe their strategic planning process

Last year, I helped a former consulting colleague prep for an operating partner interview at a PE fund here in Chicago. Good news: He got the job and is loving the work. We caught up recently and got to talking about how strategy changes when you’re working with smaller companies. After our conversation, he sent me this article - Victor Cheng's The Deep Flaw in MBB Strategic Planning - about how small companies get stuck trying to “do strategy” like big companies. It’s a fantastic read, and tees up a couple important questions:

Why do so many small companies overthink their strategy?

And what should they be doing instead?

Big Companies Love a Plan

The article’s central point is that big-company strategy has a special kind of obsession with sticking to the plan.

“There’s an enormous bias to create a strategic plan and stick to it—no matter what.”

This makes sense for the Fortune 500. Big company leaders are paid to create stability. When you have thousands of employees and billions in revenue, a big part of your job is to defend the castle. Even small changes, like tweaking a positioning statement or commercializing a new feature, can take months (or years!) simply because of the scale involved. Convincing hundreds of people, securing all those resources, and rolling out the updates across global teams is slow, methodical work. It takes a long time to get it going, and even longer to make it stick.

Small companies don’t have castles. They’re building as they go, brick by brick, in an environment that’s far less stable and way harder to forecast against. This is part of the fun of working in a small company. Getting something right means seeing the impact almost immediately. But that higher level of uncertainty means that small-company leaders need to embrace a shorter-term, more pragmatic approach to the most misunderstood word in business: Strategy.

Here’s why. At smaller companies, the “human unit of change” is tiny. Plans don’t require hundreds of micro-approvals before they can be set into motion. Just a handful of conversations (or a single meeting with the right people in the room) can give you all the buy-in you need to start closing the next gap between who you are now and the company you want to become. Beginning the process of closing these gaps - testing a new product, exploring a new market, updating your website, changing your pricing, or arming the sales team with a new play - should take weeks, not months.

That speed is the small company’s edge, but only if you are willing to adopt the kind of strategy that allows you to create and take advantage of it: A school of thought called emergent strategy.

The Power of Emergent Strategy

Emergent strategy, a concept introduced by management scholars Henry Mintzberg and James Waters in the 1980s, treats strategy as a process of discovery, encouraging leaders to adjust their course based on what they learn rather than rigidly sticking to a pre-defined long-term plan. I like Victor’s definition from his article:

"You take your best guess at what you think is the right strategic approach, try it (preferably cheaply and quickly), and see what happens."

For small companies, emergent strategy isn’t just a workaround for limited resources. It’s a cheat code. Where large companies take months to debate, approve, and act, smaller teams can move quickly—testing ideas, gathering feedback, and refining their approach in real time. Done well, it becomes a powerful three-part feedback loop: What are we doing? How’s it going? And what should we do next?

What makes emergent strategy extra powerful is that, unlike the classic big-company strategic planning cycle, the rewards don’t take years to materialize. In a small company, the feedback can be almost immediate immediate, and the payoff is tangible—whether it’s a successful experiment, a lesson learned, or a new market opportunity uncovered. And beyond the results, emergent strategy builds something just as important: emotional momentum. In a more unpredictable operating environment, a string of small wins can sustain a team’s energy and belief in a way that even the most elegant plan never could.

This is why creating a culture of short-cycle experimentation is so important for smaller businesses. It’s not about locking yourself into a rigid multi-year roadmap that protects your resources. It’s about quickly committing to your next best move that helps gain ground against the big guys. It’s about locking in on what you’re going to try over the next few weeks, deciding in advance how you’ll reflect on what you’ve learned, and repeating that cycle multiple times before your larger, more entrenched competitors can even get their shoes on.

Making those intentional, short-term decisions also gives you the clarity you need to see and respond to what’s coming at you next. You’re not abandoning the planning process. You’re reframing it. Making it more useful. And by focusing on executing and learning from shorter-term, pretty-good ideas, you reveal the path you should obviously take as it unfolds before you.

Strategy Isn’t a Map. It’s a Muscle.

If you run or work for a small company, you don’t have the luxury of overthinking. You don’t have time to wait for perfect data or sit through endless planning meetings. You don’t need to get smarter. You need to get moving.

Putting emergent strategy to work means getting off the sidelines and into the game. It means getting good at testing ideas out there in the real world instead of admiring the problem and waiting for the perfect plan to materialize. It’s about building the muscle of iteration, and using the compounding effect of the small improvements it creates to make big gains.

So stop overthinking it. Get on the whiteboard. Pick up the phone. Send the email. Mock up the prototype. Test the idea. Give it a shot.

Because if you’re a small company, the worst thing you can do is wait.