You have already paid for strategy work.
A workshop. A consultant. A business model canvas, a SWOT analysis, a competitor review, a pricing strategy, a marketing strategy. Maybe all of them. And six months later, the organisation was running roughly the same as before. Except now there was a document somewhere confirming it shouldn’t be.
It wasn’t worth it.
That feeling is not wrong. The conclusion usually is.
Before we get to what went wrong, there is one more thing worth naming.
You may have told yourself — or been told — that now is not the time for strategy work. That you need to be operationally focused. That there is too much happening right now.
This is worth looking at carefully.
The reason most founders do not have time for strategy is that their people do not have a strategy to use. So the founder has to be present. Has to answer the questions. Has to make the calls. Has to explain the priorities — again. Every day. The founder has no time for strategy because they are too busy doing the job strategy was supposed to do for them.
It is a loop. And working harder does not break it.
So what went wrong with the strategy work you already paid for?
Most likely, two things. The first is a definition problem.
For many people, strategy means plan. A list of actions. A set of projects. A roadmap of what we are going to do this year. That is not entirely wrong — strategy does tell you what you will do and what you will not do. But it is not a task list. It is not a project. A strategy built to look like a plan will be executed like a plan: tasks get ticked, the document gets archived, and six months later nobody is sure what the strategy actually was.
At the end of this essay I will share two framings for strategy that I have found useful — not definitions carved in stone, but ways of thinking about what strategy actually is that tend to change the conversation. They are worth reading before you commission the next piece of strategy work.
The second problem is translation.
A strategy workshop and a strategy you can use on an average Wednesday are two different things. They can come out of the same engagement. They often do not. Around 70% of strategies fail — not because they were bad strategies, but because they were never translated into everyday decisions. That gap between the document and the decision is where most strategy work disappears.
And this is not surprising when you consider that 85% of leadership teams spend less than one hour per month working on strategy after the initial exercise is done. One offsite, one polished deck, and then nothing until next year.
No ship navigator sets a course once and then hopes the ship arrives. They keep checking position. They adjust for current and wind. They watch the instruments. They correct course when conditions change. When they realise the original position reading was wrong, they remap the entire journey. That is not a failure of the initial navigation — it is what navigation is. Strategy works the same way. Setting a course once a year and hoping for the best is not strategy. It is an aspiration with a document attached.
Nobody is necessarily to blame for the gap between the workshop and the Wednesday. The consultant may have delivered exactly what was agreed. What was agreed may simply not have been the right thing. The question worth asking — before the next engagement, or the one after that — is not “did we do strategy work?” but “did we ask how this translates to how we actually work?”
That is a different question. It usually produces a different conversation.
There is also a structural point worth naming, because it sits on both sides of the table.
A defined engagement — two days, a clear deliverable, a fixed end date — is easier to buy than an ongoing advisory relationship. It is easier to budget, easier to approve, easier to explain to a board. That clarity is real and legitimate. But a defined engagement has a natural end point, and a natural end point limits accountability. The consultant delivers what was agreed. The engagement closes. What happens to the strategy after that is the organisation’s responsibility.
For some organisations, that is the right structure. They have the internal capacity to keep the strategy current, to course-correct when conditions change, to hold themselves accountable to the direction they set. For most organisations, that capacity has not been built yet. The responsibility lands on the founder’s desk alongside everything else — and strategy, with no deadline and no external accountability, is the first thing that gets deferred.
The question is not whether the consultant did good work. It is whether the structure of the engagement was designed to build your capacity to navigate — or to deliver a navigation system you are now expected to operate alone.
Strategy is not something you do and then leave. The scepticism is correct. It is just aimed at the wrong target.
The problem is not strategy. Very often it is how strategy was understood — by the buyer, by the consultant, or by both. What was sold, or what was bought, was not the kind of strategy work that helps an organisation run better on a Wednesday. And it is easy to see how that produces confusion, disappointment, and a reasonable decision never to do it again.
Two framings that I have found useful.
The first is for founder-led companies specifically. In a founder-led company, strategy is the founder’s thinking institutionalised — the founder’s motivations, goals, understanding of the market, and decision-making logic documented and made available to the organisation so that people can make decisions with the same context the founder would use, without the founder in the room. Not a plan. Not a task list. The founder’s thinking, converted from something one person holds into something the organisation holds. When it is only in the founder’s head, the organisation can only move as fast as the founder can be present. When it is in the system, the organisation can move on its own.
The second framing applies regardless of company type. Strategy is a hypothesis. It is your best educated guess about the route between where you are now and where you are going — and why that route makes sense given what you know today. That reframe matters because it gives structural permission to be wrong. You do not have to get it right the first time. You are probably not going to get it right the first time. When you discover that the route needs to change, or that your read on your starting position was off, or that a choice you committed to no longer holds — a hypothesis can be updated without guilt. A truth cannot. Most organisations treat their strategy as a truth. Then they feel shame when it needs to change. So they do not change it. And the gap between the document and reality quietly widens.
Treat strategy as your best current thinking, held firmly enough to act on and lightly enough to revise.
That is what navigation actually looks like.