TBM 331: Strategy & Decisiveness

Welcome to the sixth year of The Beautiful Mess!

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Strategy and Decisiveness

When people talk about "being strategic," they often discuss decisiveness.

Many of us have worked in companies where the strategy seemed to be "do as much as you can, in as short a period of time as possible." There was an unwillingness to call things out of bounds or to add guardrails. The connection to strategy flows logically: "We can't say no to anything, and we can't prioritize. Therefore, we aren't strategic."

I want to challenge that thought a bit.

Romanticized vs. Realistic Views of Strategy

There's a level of romanticism here. We've all watched action films where the vastly outnumbered hero leads their team to victory by finding the secret entrance into the fortress. We've all breathed that sigh of relief when someone created a compelling way forward by simply saying, "OK, then let's NOT try that." These moments of clarity are very salient and easy to label as "strategic." It felt like how the strategy should feel.

However, my basic observation is that while strategy involves making decisions, not all strategic decisions look decisive. A strategy might involve being indecisive about many things!

We idolize the stories of companies that laser-focus on one thing, buck the pressure, stay "maniacally focused," and win. The stories about companies that hedge their options, keep multiple irons in the fire, and succeed by being reasonably OK at many things aren't nearly as sexy. And yet most companies, including many successful ones, operate with strategies that are far less decisive than we might like. Instead of traction and positive outcomes, we'll always err on the side of optionality. Any call to "focus" must show strong momentum and proof that it is worth it, and there will always be more things we want to do than we can possibly do.

Decisiveness Without Strategy

You are a betting person and have two choices.

You can gamble big on a focused (but riskier) strategy or hedge with a smorgasbord of options. The smorgasbord won't yield huge step changes but isn't nearly as risky. Most companies die relatively slowly anyway, and there are plenty of opportunities to make money along the way. So what do you do? Do you try the swashbuckling strategy, aiming for high leverage and winner-takes-all? Or do you hedge, diversify, and opt for gradual progress?

A lot of people hedge, and that is just fine.

Importantly, you can be decisive without a "pure" inspiring strategy. Keeping multiple irons in the fire doesn't excuse spending 50% of your time multitasking, juggling projects, and getting nothing done. Many teams point to strategy as the culprit when the real problem is figuring out a reasonable way to focus and giving teams a path to call out when the lack of focus literally becomes the highest priority.

Messiness of Real-World Strategy

In many cases, even the "best" strategy offers only a slight advantage in a sea of bad options and constraints. You ask all the right questions, use the right frameworks, put together the right cascade, and realize that you're mostly ****ed, with some viable but unsexy paths forward. Yet we treat strategy as if it operates in a vacuum, ignoring the fog of competition, unpredictable markets, human psychology, and the cumulative impact of previous decisions.

It turns into a magical elixir: "If we had a strategy, everything would be fixed!" But that's not true. A strategy could as easily reveal flawed assumptions. Or you might discover that the best course of action is to incur massive tech debt and claim to do everything/anything to corner the market.

Life inside the company doesn't magically improve with a strategy.

This romanticized view of strategy often obscures the messy, real-world decisiveness needed to improve odds. It makes us overlook the practical strategic decisions teams face daily, imagining some holy grail of alignment will emerge. Strategy is always a mix of "should" and "can." Dig too deep into the "can," and you'll only do what's immediately possible, ignoring longer-term opportunities. Dig too deep into the "should," and you'll disregard current capabilities or miss the chance to evolve them.

Demystifying Strategy

To be strategic, you need to focus on the handful of areas where it makes sense to be strategic. Yes, you'll need to make big, decisive calls at times. But there will always be plenty of areas where optionality and experimentation reign. At any given time, there are only a small number of questions that really need a POV. And while you can manufacture decisiveness in the near term, no amount of decisiveness will magically survive clashing with reality in the long term. Something has to give—and sometimes that something is funding.

Be careful what you wish for!

Imagine a leadership team that follows a framework, makes "the hard decisions," and creates the focus everyone wants. It's equally likely the choices were wrong, and the pressure to converge did them in. Sometimes, it's better to admit what you don't know. The pressure to be decisive and have clear answers can be harmful if you aren't careful.

The right strategy (for right now) might not look like the bold, decisive strategy you were hoping for, but that's OK.

Conclusion

Strategy isn't a magic elixir. It's a mix of pragmatism, decisiveness, and optionality. The best strategies acknowledge a business's messy reality and embrace focus and flexibility. The real challenge is knowing when to lean into each.

I have a hunch that the "execution is everything" crowd is sick of armchair strategy and needs people to meet them in the middle somewhere.

Here's a helpful exercise.

Ask your front-line teams where they constantly spend a lot of energy navigating a hard trade-off. An example might be: "We constantly find ourselves lost when it comes to whether to invest in going up-market or making our original customers happy."

Then ask yourself: "Is this an area where we need to weigh in right now, or do I need to explain to our front-line teams that this juggling act is currently a fact of life?"

It seems simple, but everyday decisiveness with a dash of strategy can go a long way.