How to choose a strategy advisor

For founders weighing outside strategy help: how to tell what you actually need, what good looks like, and how to judge any advisor, including us.

By · · 8 min read

There is a moment most owners reach more than once. A decision is bigger than the ones you usually make alone, the stakes are real, and you catch yourself thinking you might need outside help. Almost in the same breath, you distrust the thought. You have seen the deck that said nothing, the framework that fit every client because it fit none of them, the invoice that bore no relation to anything that changed. So you sit with two competing instincts: this is too important to get wrong alone, and I do not want to be sold to. Both are correct. Act on the first without falling for the second.

This piece is the hub for that decision. It is also, unavoidably, written by an advisory firm, which raises a fair question we answer plainly below: are we not biased? Yes. So here is how to judge any advisor, and the test that separates advice from selling.

The honest first question: do you need an advisor at all

Before you choose between firms, decide whether you need one. There are roughly three things people reach for an advisor to supply.

The first is judgement: a second mind on a decision you will still own, to test your thinking, name what you are avoiding, and improve the call. The second is hands: capacity to do work you have scoped but cannot staff. The third is a decision you have already made and want someone external to bless. That third is worth catching early: hiring an advisor to ratify a decision is an expensive form of reassurance, and a good advisor will decline the role.

Sometimes the honest answer is that you need none of them. The decision is yours, you have the information, and what you feel is the ordinary discomfort of a hard call rather than a real gap in judgement or capacity. A good advisor will say it to your face: this is yours to decide, save your money. If the answer is genuinely judgement or hands, read on. If it is the third, the work to do is internal.

The kinds of help, and what each is for

"Consultant" covers a wide field, and the categories matter because they answer different needs. None is better in the abstract; each is better for something.

An independent adviser is one experienced individual, usually senior, who works directly with you. You get continuity and a single accountable mind, with little overhead. The trade-off is bandwidth: one person can think alongside you and shape the work, but cannot also produce a large body of analysis quickly. Best when the need is judgement.

A boutique firm is a small team built around a defined specialism. You get senior attention with enough hands to do real work, and depth in their area. The trade-off is range: a boutique is sharp inside its domain and thinner outside it, so the fit depends on whether your problem sits in theirs.

A large firm brings scale, breadth, and a recognised name. For a genuinely large, multi-workstream problem, that capacity is the point. The trade-off for a smaller business is that you may buy a brand and a methodology and find the day-to-day work done by people more junior than those who pitched. Matching a large-firm engagement to a small-company problem is the most common and expensive mismatch in this field.

A fractional executive is a senior operator who takes a part-time seat inside your business: a fractional marketing or finance lead, for instance. You get embedded senior capacity at a fraction of a full-time cost. The trade-off is that the role is a seat to fill, not a question to answer, so the value depends on whether the seat is the thing you actually need.

An interim is a full-time senior hire for a defined period, typically to hold or turn around a role through a transition. You get focus and presence; the trade-off is cost and the fixed term. Fractional, interim, and consultant are different ways of borrowing senior capability: choose by the need, not the label.

What good looks like

Across these categories, the marks of a good advisor are consistent, and you can spot most before signing anything.

A good advisor asks about your decision before pitching a solution. The first conversation is mostly them understanding what you are trying to decide and why it matters, not describing their process. David Maister, Charles Green, and Robert Galford, in The Trusted Advisor, put intimacy and low self-orientation at the centre of trust: the advisor's attention is on your problem, not on winning the work. Edgar Schein makes a related point in Humble Consulting and Process Consultation: real help starts by understanding the client's situation, not by rushing to apply expertise. The "expert" who arrives with the answer before they understand the question is usually selling a product.

A good advisor will decline work that is not theirs. They will tell you when your problem sits outside their competence, and resist scoping the engagement to include things you do not need. Willingness to walk away from revenue is the clearest signal that their judgement is for sale and their integrity is not.

A good advisor leaves you more capable than they found you. The aim is that your team can do more after the engagement than before, not that you are bound to call them again for the next variation of the same problem. Peter Block, in Flawless Consulting, frames this as contracting for the client's ownership rather than for dependence.

The warning signs

The mirror images are just as legible, and worth naming because they are easy to rationalise.

Be wary of the advisor who sells a methodology rather than judgement. When the pitch centres on their proprietary framework or five-stage system, you are being sold a thing they apply to every client rather than a mind that engages with your situation. Frameworks are useful as scaffolding; they are a warning sign as the product.

Be wary of the advisor who cannot say no. If in every conversation your situation turns out to be exactly what they do and your problem exactly what they solve, their diagnosis is determined by their inventory.

Be wary of billing for activity rather than outcomes: hours logged, meetings held, slides produced, with no line drawn to a decision made or a capability built. Activity is easy to invoice, hard to value.

And be wary, especially, of the advisor who claims hands-on operator experience in your specific field that they do not have, in order to win the work. An advisor who has run a strategy process for many businesses brings something real and worth paying for: pattern recognition, method, an outside view. That is a different thing from having run a business exactly like yours, and a straight advisor will not blur the two. If someone implies they have walked precisely in your shoes when they have instead helped many who have, treat the overclaim as data about everything else they tell you.

Aren't you biased, writing this?

Yes. We are an advisory firm, and we would benefit if you decided to hire one. It would be dishonest to pretend otherwise, and pretending would itself fail the test we just laid out. So rather than ask you to trust us, we give you the standards and ask you to hold us to them.

Judge us, and anyone else, on the marks above. Did we ask about your decision before describing our process? Did we tell you, at any point, that you did not need us, or that another kind of help would serve you better? Can we say no? Is the engagement scoped to an outcome, or to a quantity of our time? Will you be more capable when we leave? Those questions work on us exactly as they work on a competitor, which is the point of writing them down.

The single best test sits underneath all of them: a good advisor will tell you when not to hire them. An advisor who can always find a reason you need them is selling, not advising. We would rather lose work by being honest that it is not ours than win it and serve you badly. That is the only basis on which advisory work is worth buying.

Scoping so you can tell whether it worked

Most of the bad experiences people carry into this decision were not betrayals; they were scoping failures. To avoid repeating one, insist on three things before any work begins.

First, a question. What decision is this engagement here to serve? If it cannot be stated in a sentence, it is not ready to be bought. Second, a success criterion: how will you know, at the end, whether it was worth it? "We will be able to decide X with confidence" is a criterion; "we will understand our market better" is not. Third, a defined end: a good engagement has a shape and a finish, not an open meter. Block's discipline of contracting is exactly this: agree what each side owns and what done looks like, before the work.

Scope this well and you remove most of the risk that worries you, because you can tell whether it worked. Scope it badly and even a good advisor will struggle to give you something to judge.

The questions to ask any advisor, including us

If you take one thing into the first conversation, take these. What decision is this work here to help me make? Will you tell me if I do not need you, or if someone else would serve me better? What will be different when this engagement ends, and how will we both know? Is the work scoped to an outcome with a defined finish? And will my team be more capable afterwards, or more dependent?

How an advisor answers these, before you have paid anything, tells you most of what you need to know. The right one welcomes the questions, because the right one wants you to be a clear-eyed buyer. Ask them of us too.