The Sad Emoji: Making Strategy Planning Season Not Stink

Last week an email arrived from a former colleague. "For the whole week, I'll be in strategy sessions." A sad emoji closed the sentence.

We have been there. We have also caused it.

Years ago, we ran a strategy season for a business we led. We built the template of 20 slides, the same 20 for every business unit, sent out three weeks early so no one would be caught unprepared. People filled boxes. We produced over 100 pages. When it was over, we asked one of our managers what our strategy was. He said, "Grow profitably in attractive markets." He was quoting our own summary slide back to us, word for word.

That was the problem.

Every year, between September and November, strategy season arrives. Consultants dust off their frameworks. Calendars fill. Decks multiply. Smart people spend weeks filling in slides someone else designed and call it strategy. It is not strategic thinking. It is planning at best and theater at worst.

The industry has made this look easy. Buy the framework. Follow the steps. Former executives fill LinkedIn with the magic formula, some of them listing "Strategist" under their name as if it were a credential you earn once and carry forever. But the consultants are not the ones to blame here. We buy the framework because filling in boxes is more comfortable than admitting we don't know how we're going to win.

So let us say something less comfortable.

Strategy development is messy. It is continuous, not seasonal. It does not guarantee success. And it requires humility. The humility to admit that some things are unknowable and no amount of analysis will make them knowable. Done well, it gives you slightly better odds. Over time, slightly better odds compound into a decisive advantage.

That is the honest promise. Not certainty. Better odds consistently applied.

Here is what most processes get wrong: they overweight planning and underweight thinking. Strategic planning is the document. Strategic thinking is the discipline of choosing what you will do, what you will not do, and why. Most companies spend months on the document and almost no time on the thinking that should precede it.

Think first. Plan second. It sounds obvious. It is surprisingly rare.

And here is something the frameworks won't tell you: it does not matter where you start. Strategy is like planning a trip. You can focus on the destination or the vehicle and can begin with either one. Some leaders start with where they want to arrive and work backward to what they'll need. Others start with the vehicle they actually have — the cash, the people, the plant, the customers who already trust them — and figure out how far it can carry them. Both work.

What does not work is spending the whole season drawing a beautiful map without deciding where you're going or understanding what capabilities you have. Or worse, copying someone else's map and pretending it's yours.

What matters is the balance of goals, capabilities, and initiatives, and adjusting them continuously as you learn. Markets shift. Customers change. Competitors surprise you. The strategy that made sense in January may need rethinking by June. That is not failure. That is the road changing under the vehicle, which is what roads do.

Which brings us to the part offsites avoid. Constraints. Good strategy knows its constraints and respects them. Your vehicle has a fuel range. Your team has a capacity. Your balance sheet has a floor. Many strategies we have seen are not strategies but wish lists with timelines.

Ben Horowitz, former entrepreneur and founder of the world’s most prominent venture capital firms, put the cost of ignoring constraints plainly in his book The Hard Thing About Hard Things: "The hard thing is laying people off when you miss the big goal… The hard thing isn't dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare."

Naming constraints out loud is what separates a strategy session from theater.

Back to our colleague and her week. We know what those sessions look like. Predetermined formats. Someone asking the group to populate the boxes. A facilitator moving through the agenda on time. Lots of activity. Very little thinking.

That is not strategy. That is compliance dressed up as strategy.

So here is our challenge to you before your next session. Walk in with one question written at the top of your page: "How, specifically, are we going to win and against whom?" If the room cannot answer it in three sentences by the end of the week, the deck does not matter. Argue about that question. Argue about the right things.

Done right, you should walk out with energy and conviction.

Not a sad emoji.