Bringing in an external strategy consultant is one of those decisions that tends to get made either too early, when the problem is still vague, or far too late, when it has hardened into something expensive. Neither is a judgement failure. It is genuinely hard to tell from the inside which of those two states you are in.
This is a way of working that out before you spend anything.
The wrong reason to hire one
The most common reason is also the weakest: the leadership team cannot agree, and an outside voice is expected to break the deadlock. That is not a strategy problem, it is a decision-rights problem, and no consultant can solve it for you. If nobody in the room has the authority to choose, an external recommendation simply becomes another opinion to disagree with, at a higher cost.
The second weak reason is validation. If the answer is already decided and what is wanted is a document that supports it, you are buying reassurance rather than thinking. It is expensive reassurance, and everyone in the organisation can usually tell.
Five situations where it genuinely earns its money
1. You can describe the symptom but not the problem
Growth has flattened, the pipeline looks fine, and nobody can say why. When a team can list what is happening but cannot agree on what is causing it, the useful work is diagnosis, not execution. That is a specific skill and it is the one most often skipped, because diagnosis feels like a delay when everyone wants action.
2. The organisation is too close to it
Every business accumulates assumptions that were once decisions. They stop being visible because everyone shares them. An outsider is useful here purely because they do not know what is obvious, which is why the naive question is often the valuable one.
3. The internal answer keeps being the same answer
If the last four strategic responses have all been a version of the previous one, the constraint is probably in how options are being generated rather than how they are being chosen. That is a creativity problem in the commercial sense of the word, and it is more common in senior teams than most would admit. It is worth reading why creativity is a commercial skill rather than a department before assuming the issue is effort.
4. You cannot explain the strategy simply
A strategy that takes forty slides to convey is usually several strategies wearing one name. If people two levels down cannot repeat the point without the deck, it will not survive contact with the organisation, whatever the document says. That failure mode is covered in why storytelling changes behaviour in business.
5. Something has genuinely changed
A new competitor, a shift in how customers buy, a technology that resets the cost base. Strategies are built on assumptions about a market. When those assumptions move, the strategy needs revisiting rather than defending, and organisations are structurally bad at reopening decisions they have already announced.
What good looks like
A useful engagement has a small number of features you can check for before committing.
- It starts with the problem, not the deliverable. If the first conversation is about scope and format rather than what is actually wrong, that is a warning.
- It involves your people. Strategy developed away from the team who must deliver it arrives as an instruction, and instructions get quietly ignored.
- It produces a decision, not a report. The output should make something possible that was not possible before.
- It is honest about what is not known. A consultant who is certain about everything has stopped thinking and started presenting.
- It leaves capability behind. The best sign is that you need them less next time, not more.
The senior-adviser model
Not every problem needs a project. A lot of the most useful consultancy is closer to having a smart, experienced, unaffiliated person to think with, someone with no internal politics and no career riding on the answer.
That is the shape of Kevin Chesters’ strategic consultancy work: thirty years in the commercial application of creativity, including as Chief Strategy Officer at W+K London, Dentsu and Ogilvy, and Head of Consumer Strategy at BT, now applied independently to client problems. His own description of it is deliberately unfussy: let me take something off your to-do list.
For a marketing or leadership team, that often matters more than a large engagement. The value is in having someone who has seen the pattern before and will say so plainly.
A test before you commit
Write down, in one sentence, what you want to be true in twelve months that is not true now. Then write down what you believe is stopping it.
If you can write both sentences and your team agrees with them, you probably need execution support rather than strategy. If you can write the first but not the second, or your team writes five different versions of the second, that is the case for outside help, and it is a strong one.
The short version
Bring in a strategy consultant when the problem is genuinely unclear, when shared assumptions have become invisible, when the same answer keeps reappearing, when the strategy cannot be explained simply, or when the market has moved. Do not bring one in to settle an argument or to validate a decision already made.
If you want to talk through which of those you are actually in, get in touch. That conversation should be useful whether or not it goes any further. More on Kevin’s background.