(2025-08-09) Cutler Tbm271 Diagnosing Your Companys Strategy Problem

John Cutler: TBM 271: Diagnosing Your Company's Strategy Problem. From your vantage point, it feels like no one in your company is being strategic. The answer to everything is, "But why can't we do both?" No one seems willing to make a decision.

From your vantage point, the strategy seems to be, "Try to do as much as possible, and see what sticks."

In this post, I want to give you a way to diagnose what is going on. Too many people default to a simplistic explanation like, "We just need a strategy." Well, yes, that helps, but it is critical to diagnose why the strategy you're satisfied with isn't emerging.

Let's divide up the problem into three pillars:

Information and Insights

For some companies, the key issue is a lack of situational awareness, a lack of humility to accept the current situation, or the inability to tolerate uncertainty when it exists (and fabricating certainty).

The Game and Options

Next, you have knowledge about the game you are playing and the strategic options at your disposal, as well as a shared understanding of that game and those options.

Part of knowing the game and its options is understanding that you'll sometimes not know the game, sometimes you can shape new games, and occasionally new dynamics enable new, untested options. In other words, unlike sports, there isn't always a fixed game with a relatively constrained set of options. (ill-structured, infinite game)

In business, you have your choice of games, you can shape/change the rules, and you can invent new options for playing the game. (game-rule)

game/option awareness also involves realizing that a company ecosystem is a collection of game-playing actors and domains. (games theory)

Now What?

The Now What? may be naturally constrained by the context, game, and options. But it may also be constrained by competing agendas, goals, levels of risk tolerance, and other factors.

Many companies 1) have good insights, 2) agree on those insights, 3) the game is fairly obvious, 4) their options are fairly obvious, but 5) there is no clear "winner." They are in a logjam and stalemate, and often NOT because they are incompetent or suck at decision-making, but rather because there are no "good" options (each option will cause pain). It is easy to romanticize big, bold, strategic bets when you don't have to sit there and explain to investors why they should be excited about the risks involved.

Connecting these three dimensions is probably a meta-dimension that roughly boils down to integrating these areas regularly. Many companies end up losing because they stubbornly hold on to a view of their context, their game, and their "old" way of aligning from 5-10 years ago. And plenty of companies get carried away with reactive course corrections because of the latest tech fad, macro environment shift, etc.

So What? Our Strategy Is Non-Existent!

How do you put any of this to use?

More Information and Insights

Suppose you are flying without a radar, or no one can agree on what the radar is telling you.

Your (first) job then is to get more information into the room, and get more eyes on that information (which is a strategy unto itself).

Game Clarity (and Honesty)

The next thing you need to do as an individual contributor, manager, or director is to be honest with yourself about the "game" your company is playing. We imagine the game is to "win," or to "serve customers," or "survive and thrive." But realistically, in many cases, the game is to provide fairly predictable returns to investors, even if that means a slow descent into mediocrity.

In other situations, the game is a battle of games between the people in the company who will benefit from a big upside (and have a strong hedge against the downside) vs. employees who got their stock later, and who have no hedge. There are all sorts of games. (games theory)

Pay attention to narrative clashes and differences in perspective when it comes to the game and the options.

Now What? Realism

Finally, it is critical to realize how hard it can be to commit to a Now What? when there is incomplete information. This is where romanticized strategy and real-world strategy clash.

Imagine having to be the person sitting in front of the board saying, "Well, you know, we ARE growing at a healthy 30% year over year, but you know what, we're going to let that slide to around 20% next year to make some big bold bets that we're SURE you'll love!"

The key point is that you need to explore why your company's strategy is weak and how it's causing indecision and a lack of focus. It isn't always because people are "bad" at strategy (though that does happen), and it isn't always things that can simply be willed away with a good Miro board exercise.