You Don’t Need a Better Strategy Yet

Before you open the deck one more time, try reframing your problem.

The hardest part of strategy is the pressure to have the answer.

That pressure of the perfect answer can sometimes be paralyzing; most of the time, to get to the best answer, you need a different frame.

When you feel stalled, it’s usually not because you lack insight or data. You’re stuck because you’re solving the problem the same way, through assumptions that need more questioning. Even strong thinking can produce increasingly refined versions of the wrong thing.

Reframing changes the conditions under which an answer is allowed to exist.

Below are a few of my go-to ways of doing that.

Ask what the system is optimized for

If something isn’t working, assume it’s doing exactly what it was designed to do.

A vaguely defined brand is often optimized for internal alignment. A slow product roadmap is often optimized for risk avoidance, or there isn’t enough customer insight in the loop.

Calling these outcomes “failures” keeps your analysis shallow. Asking what they’re optimized for forces you to look at incentives, power, and tradeoffs. That’s where the real problem usually is. The best strategy will not work if you cannot align the system and incentives to support it.

This reframe shifts the work from fixing symptoms to reworking the underlying structure. A company that wants to be more innovative around sustainability, for example, can’t get there through messaging alone. Without sourcing protocols and executive buy-in, it isn’t a marketing problem at all. It’s an organizational one.

Treat constraints as information

Most teams treat constraints as things to work around: budget, legal, timing, internal politics. Strategically, those constraints are useful.

Constraints exist to protect something. Budget limits protect risk tolerance. Legal rules protect precedent. Timelines protect capacity or authority. When a constraint won’t move, it’s usually because moving it would surface a conflict the organization isn’t ready to confront.

If you don’t understand what a constraint is protecting, you’ll design something that dies quietly later. Reading constraints properly often tells you more about the system than any research deck. Treat constraints as thought partners.

Replace “What should we say?” with “What would have to be true?”

Don’t back into the message, even if solving for the tagline feels like the shiniest thing that will make the client happiest.

“What should we say?” assumes the audience is ready to hear you and that the surrounding conditions already exist. Often they don’t!

It presumes belief, relevance, and timing have already been earned.

A better question: what would have to be true for this to land?

• Who or what would people need to trust?

• What would the timing have to look like?

• What would they need to believe about their own situation for this to resonate?

Working backward from those conditions shifts the work. Instead of debating language, you’re designing the environment in which language actually matters. When those conditions are right, the words tend to arrive with much less force.

Think about strategy as wayfinding

Clarity is useful — but only when the conditions for it exist.

Schiphol Airport signage, Amsterdam. Photo by Julian Walker via Unsplash.

In complex or overwhelming situations, people don’t need everything explained. They need orientation: they need to know where they are, what matters now, and what can safely wait.

Thinking of strategy as wayfinding helps here. A wayfinding system doesn’t show everything at once. It sequences information based on where someone is and where they’re trying to go.

When the task feels daunting, ask what needs to change in the next month, the next six months, the next year. That act of sequencing forces realism into the work. It also makes the strategy easier to implement for you, your client, and anyone responsible for carrying it forward.

Evaluate what you make possible

Instead of stressing about whether you’ve landed on the right answer, ask what the idea makes possible.

If this strategy works, what changes?

• Do decisions move faster?

• Does it unlock behavior that was previously stalled?

• Does it give the organization a future it can act toward?

Strategy doesn’t have to be cynical. It can be an optimistic act! Not in the sense of being naive, but in the sense of expanding what feels doable. Momentum is information. If an idea creates movement, alignment, or energy, that’s usually a signal worth paying attention to.

Design for the tension

Most of the time, you’re managing a tension, not solving a problem.

For example, for a community program you’re probably evaluating:

• Scale versus intimacy

• Speed versus trust

• Control versus participation

Trying to eliminate one side of the equation usually strips the work of dimension. Ignoring the tension altogether produces a strategy that feels vague to action.

The job is to name the tension clearly and design within it. Strong strategies don’t resolve tensions; they hold them deliberately and make them an advantage.

A worksheet

The answer isn’t always the issue.

When strategy stalls, refinement is often the default response. It feels productive, and it keeps the work moving. But it doesn’t change the conditions the work depends on. Before refining further, check whether the frame that produced the answer still holds. If it doesn’t, no amount of polish will help.

And finally: last call for my live recording of the Hip Replacement podcast IRL tomorrow at the Air offices in New York! Register here.