Questions to Ask a Brand Strategist
Questions for a first conversation with a brand strategist you are considering hiring, whether an independent consultant or an agency team. They cover scope, research, deliverables, pricing, and who does the actual thinking.
The questions
Open any question for the note
What kind of brand problem do you get called in for most often?
Why ask it
Strategists specialize more than their websites suggest: repositioning after a merger, naming, category creation, or cleaning up a portfolio. If your problem is not on their list, the rest of the conversation matters less.
Looking at us now, what stands out first?
Why ask it
Asks for a reaction before they have been paid, which most will give in general terms. You are testing whether they noticed something real or opened with a critique of your logo.
How do you tell a brand problem from a sales problem?
Why ask it
A serious answer will point at evidence: whether people who know you still choose someone else, or whether nobody knows you exist. Anyone who treats every problem as a brand problem will sell you work you do not need.
What does the engagement look like week by week?
Why ask it
You want a shape you can plan around: interviews, then synthesis, then options, then a decision session. Vagueness here usually means the process is improvised around whatever the client will sit through.
Who from our side do you need, and for roughly how many hours?
Why ask it
Brand work fails when the founder or the head of sales cannot make the sessions. Getting the demand on your team stated up front lets you say no before you have signed.
What research would you do, and how many of our customers would you actually speak to?
Why ask it
Ask for numbers and method. Six real customer conversations beat a hundred page desk review, and a strategist who plans neither is going to hand you back your own opinions.
How do you work out who we are not for?
Why ask it
Deciding what to give up is the hard half of positioning. Someone who only talks about audiences to win, and never about ones to release, is describing marketing rather than strategy.
How do you handle it when the founder and the market disagree about what the company is?
Why ask it
This is the recurring situation in brand work. Listen for how they have handled it before, since the answer tells you whether they will hold a position or simply reflect the loudest person in the room.
What exactly do we get at the end?
Why ask it
A document, a set of decisions, messaging your team can use, or artwork are very different outcomes. Ask to see a real deliverable from a past project, with the client details removed.
What is the smallest version of this that would still be worth doing?
Why ask it
A good strategist can describe a two week version and tell you honestly what it would leave out. Anyone who says the full program is the only option is protecting their fee, not your outcome.
How would we know in six months whether this worked?
Why ask it
Push past awareness. Useful answers involve things you can observe: which deals stop stalling, what people say back to you unprompted, what your sales team stops having to explain.
Which measures do you consider brand measures, and which do you ignore?
Why ask it
The second half is more informative. A strategist willing to dismiss a popular metric, and say why, is thinking rather than reciting.
Can you tell me about a project where your recommendation was not adopted?
Why ask it
Everyone has one. What you learn is whether they blame the client, and whether they understood the internal politics that killed it, which is the same skill they will need with you.
Do you do the naming, identity, and copy yourself, or hand off?
Why ask it
Both models work, but the handoff is where brand projects most often die. If they hand off, ask who to and how the brief travels.
How would you brief a design or copy team on your strategy?
Why ask it
Ask to see a brief they have written. It is the most reliable evidence in the whole conversation, because a strategy that cannot be briefed cannot be built.
What would you need us to stop doing while this is underway?
Why ask it
A candid answer, pause the website rebuild, stop the new campaign, shows they understand that strategy has to precede execution. Silence here means you will pay for work twice.
Have you worked with a company at our stage and size?
Why ask it
The difference between a twelve person company and a twelve hundred person one is not scale but who has to be persuaded internally. Ask for a comparable example, not an impressive one.
Who else would be on this, and who does the thinking?
Why ask it
In agencies, the person in the pitch is often not the person on the work. Ask who writes the strategy, who attends the sessions, and get the names in the proposal.
How do you price this, and what makes a project go over?
Why ask it
Fixed fee, phased, or by the hour all behave differently when scope shifts. The overrun question is the important one, and the usual answers are added stakeholders and reopened decisions.
What usually goes wrong on projects like ours?
Why ask it
A closing question that separates the experienced from the polished. Real answers, the decision maker stopped attending, the team never adopted the language, come with what they now do to prevent it.
Engaging a brand strategist
Practical guidance for the conversation itself
Know what you are buying
- Decide before the call whether you want a decision made, a set of words your team can use, or new visual identity. These are three purchases and confusing them is the most common cause of disappointment.
- Write down the symptom in plain language: deals stall at a certain point, two products compete for the same customer, nobody can describe what you do. Bring the symptom, not a diagnosis.
- Separate the strategy engagement from the identity work in your budget, even if one supplier does both. It keeps you able to stop after the first part.
- Know who the decision maker is and whether they will attend. If they will not, postpone the project rather than hoping.
Signs worth paying attention to
They ask you harder questions than you ask them
The best first meetings tip about halfway through, and you find yourself being interviewed about customers, pricing, and where revenue actually comes from. A strategist who only presents is not diagnosing.
They lead with visuals
A moodboard or logo concepts in a first meeting is a sales device. It is impressive and it tells you nothing about whether they can find a position, since the design decisions come after the strategy work, not before it.
They are specific about tradeoffs
Positioning means giving something up: a segment, a price point, a product line. Someone who promises to broaden your appeal to everyone is describing an outcome that does not exist.
They talk about your staff
Brand work that never reaches the people answering the phones changes nothing. Look for a strategist who asks about internal communication and training as part of the scope.
Before you sign
- 1Ask for a real deliverable from a past engagement, anonymized, and read it end to end. Case studies are written by marketers; deliverables are written by the people doing the work.
- 2Take two references, and ask each what has actually changed since the project and whether the language stuck internally.
- 3Get named people, dates, and the number of sessions into the proposal, along with what counts as a change of scope.
- 4Agree the handoff explicitly: who briefs the designers and writers, and who is answerable if the execution does not match the strategy.