Messy Strategy is the best kind of strategy

Strategic thinking suffers from the same flaws as all ivory tower thinking: ludic fallacy, detachment from reality. Traditional strategic thinking is the equivalent of waterfall development: let us think of the big things and draw boxes on a flipchart we’ll then give to the plebs to execute.

Traditional strategic thinking values clear thinking and black/white decisions above everything else, to the point of isolating itself from reality, because reality isn’t that clear and it's an impediment. In a way, yes, all strategic thinking is an approximation, a simplified model, that's true, but when it goes too far it's meaningless.

That’s why most strategies are the same time empty and useless. Empty because the sanitized theoretical discussions manage to engage noone, touch no sensitive points, surface no pain and inspire no hope. Useless because they are dead as soon as you leave the room because they have no buy in, no traction, no realism.

The best thing about traditional strategic thinking is the desire to explore options and ideas that are potentially far removed from the current reality, to free our minds to think in new ways. That is a worthwhile thing to do, but it’s far from the only thing one must do in a strategy workshop.

Strategic conversation that don’t have lively debates, even conflict, are not touching what matters.

Strategic conversations that don’t also talk about the how are detached from reality.

Good strategy tends to be somewhat dialectic. I know this goes counter to the current zeitgeist which values extremely simple and direct strategy statements, for the sake of focus and clarity. I like focus just as much as the next guy, and I don’t want to get paralyzed in analysis one bit, but tension and conflict is a key part of strategy. We’ll spend more time servicing clients while we’ll also spend more time on growing our employees. We’ll have cheaper and better versions of our products. This is not avoidance of hard decisions, these are key business tensions that need to be navigated at all times. Any fool can do one thing and one thing only, but good businesses need to do a bit more than one. One product, maybe, but one thing, strategically speaking, not often. Yes, there’s a lot of crap that businesses need to drop, mentally and physically, but don’t give in to oversimplification and lose all sophistication just for the sake of being able to have sound bites that begin with “one thing and only one thing matters”. Strategies don’t need to be able to be fully explained in tweets. Businesses don’t need to be understood from one TED speech. Well, in a way they do, when it comes to the elevator pitch, to the intended benefits of your product, but not to your highly qualified people who do this 8 hours a day and need to actually make it work.

Up and down, high and low, all in the same session. Think big and unbounded, then ask yourself who and how will do it. Big picture, deep dive. Big picture, deep dive. You don’t need all the answers, but have some and get all the questions. Focus on key points, on tensions, on disagreement, on conflict: that’s where the energy is, that’s probably where the innovation is too. Make hard decisions, most of the ideas do indeed need to be dropped and killed.

And, most importantly, think in terms of teams and their routine. Delivering on a strategy is in many ways the same a delivering on any other project. Who is the team accountable for the strategic chapters? Are they committed? Are they a good team, do they work well as a team? What is their routine for recurrently meeting and pushing forward pieces of the strategy, in an MVP style, doing validated learning, adapting and communicating as they go?

Yes, good strategy is clear but is also kind of messy. It’s tense, it thrives in a narrow place, at the intersection of conflicting forces, it’s on the bleeding verge of the unknown and it frequently needs “odd couples” of complementary personalities and tendencies to make it happen. And good strategy sessions are almost always emotional, tense, conflictual even, and yes, messy. Good teams can take it, great teams need it. You can’t talk about what really matters in a even tone of voice, while drawing boxes. If you find yourself doing that, you’re not talking about what really matters.