What Actually Happens in a Brand Strategy Session?
Most founders I work with have heard that they need brand strategy. Very few of them know what that actually involves.
Some picture a workshop with Post-it notes on a whiteboard. Others assume it’s an extended version of a brief — a longer, more structured conversation about logos and colours. A few have been on the receiving end of a consultant asking questions they already knew the answers to and charging them accordingly.
None of those are quite right. So here’s an honest account of what a brand strategy session actually involves — why it works the way it does, what you’ll be asked, and why the questions that seem most indirect are usually the ones that matter most.
It starts before you arrive
A good strategy session doesn’t begin the moment you sit down. It begins the moment you agree to have one.
I send a short briefing document in advance — a handful of questions designed not to get polished answers, but to get you thinking. Things like: what does your business do better than anyone else, and how do you know? Who is the client you’d clone if you could? What would you change about how your business is currently perceived?
These aren’t questions most people have formal answers to. That’s the point. The responses you arrive with — even the half-formed ones, even the ones you’re not sure about — are useful. They tell me where the clarity already exists and where it doesn’t.
What gets asked — and why
The session itself typically runs two to three hours. It’s a conversation, not a presentation. There’s no deck to sit through.
I ask a lot of questions. Some of them feel strategic: what’s your competitive advantage, who’s your target market, what’s the problem you solve? These are the ones founders expect, and they usually have prepared answers.
But the questions that tend to unlock the most useful thinking are the ones that catch people off guard.
Things like: if your business shut down tomorrow, what would your best clients actually miss? Not the service — what would they miss? Or: what’s the thing you’re best at that you almost never lead with, because you assume everyone can do it? Or: when a sale goes wrong — when the right kind of client chooses someone else — what’s usually the reason?
These questions are indirect because direct questions about brand positioning tend to produce direct, generic answers. The oblique route — through values, through failures, through things taken for granted — often surfaces the material that actually makes a brand distinctive.
The gap that almost always shows up
There’s a pattern I’ve noticed across hundreds of these sessions. There’s almost always a gap between how a business sees itself and how the outside world experiences it.
Not always a dramatic gap. Sometimes it’s subtle — a company that’s genuinely collaborative but whose brand comes across as arms-length. A founder who leads with warmth in every client conversation but whose website reads like it was written by a committee. A service firm with a genuinely differentiated approach that never quite makes it into the language they use to describe what they do.
The strategy session is largely about closing that gap. Identifying what’s true about the business — not aspirationally, but actually — and making sure the brand expresses it.
What you’ll get out of it
By the end of a well-run strategy session, a few things should have shifted.
First, the brief gets sharper. You’ll have a clearer sense of who the brand is for, what it needs to communicate, and what it should feel like — not just look like. That clarity feeds directly into every creative decision that follows. It’s what prevents logo revisions spiralling into six rounds because nobody agreed on what the brand was trying to say.
Second, you’ll have surfaced some things you weren’t expecting. That’s not a sign the session is going wrong. It’s a sign it’s working. The questions that make you pause — the ones that produce a ‘well, I’ve never quite thought about it like that’ — are usually the ones that lead somewhere genuinely useful.
Third, there’ll be a document. Not a fifty-page brand book — a clear, working summary of the strategic foundation: the positioning, the target audience, the brand personality, the key messages that need to run through everything that follows. The strategy output is a brief, essentially. A brief for everything else.
Why it matters that you do this first
Brand strategy sessions feel slow to people who are in a hurry to get to the design. I understand the instinct. There’s a launch coming. There’s a pitch next month. The website needs to be updated before the big conference.
But the sessions that get skipped are precisely the ones that explain why brands end up being redone eighteen months later. Not because the design was bad — but because it was built on assumptions nobody had tested.
The work that comes out of a good strategy session doesn’t just look right. It holds up. When a client goes back to it six months later, it still makes sense. When they’re briefing their team on tone of voice or explaining to a new marketing hire what the brand stands for, the answers are already there.
That’s what the session is for. Not to slow the project down — to give everything that follows a foundation it can build on.
I run brand strategy sessions with founders and business owners across Surrey, South London, and the wider UK. If your brand is feeling unclear, or you’re about to start a new project and want to do the thinking before the designing, a 30-minute Discovery Call is a good place to start.