The questions I ask before I take any product brand

Not every project is a fit. Before I say yes, I ask questions that protect both sides from polite failure-the kind where everyone is nice, the work looks busy, and nothing actually changes. Charm is not a brief. Budget is not a strategy. And “we just need a quick redesign” is occasionally true, but more often a symptom wearing lipstick.

This is a transparent look at how I choose collaborations for strategy-led product and web work. Founders can use the same list in reverse: if you cannot answer these well, you may not be ready for an external partner-or you may need a clarity sprint before a build sprint. Related reading: before you spend £10,000 on marketing, five questions.

Why fit questions matter more than chemistry

Chemistry gets projects started. Fit keeps them useful. Mis-fit work wastes the client’s runway and the strategist’s attention-then both parties write vague testimonials about “great process” while the metrics stay flat.

First Round Review and Y Combinator’s Library both circle a practical theme: early companies need partners who increase learning speed, not vanity output. My questions are designed to detect whether we can increase learning speed together.

The five client-fit questions

1. What decision are you trying to make easier for customers?
2. What have you already tried-and what did you learn?
3. Who decides, and how quickly can we ship changes?
4. Are you open to cutting features, copy, or channels?
5. What does success look like in 30 and 90 days?

Question 1: what decision are you trying to make easier?

Marketing briefs often start with tactics. I start with the customer decision. Are we trying to make it easier to understand the offer, trust the company, start a trial, book a demo, or expand a seat count? Different decisions need different designs.

If the answer is “all of them,” we do not have a project-we have a wish list. Product strategy before screens exists for this moment. So does repositioning in 60 minutes when the decision itself is muddy.

Strong answer example: “Series A B2B buyers hesitate because they cannot tell if we replace their agency or sit beside it. We need the site and onboarding to make that choice obvious.” Weak answer example: “We need to look more premium.” Premium is a costume; decisions are the play.

Question 2: what have you already tried and learned?

I am not looking for a perfect experimentation culture. I am looking for intellectual honesty. Teams that have tried nothing sometimes need foundational clarity. Teams that have tried everything and learned nothing often need diagnosis more than new tactics.

• Useful: “We ran paid search for six weeks; CTR was fine, activation was poor-so we suspect onboarding.”
• Useful: “We redesigned once; demos rose, close rate did not-sales still fights pricing confusion.”
• Risky: “We need fresh creative” with no theory of why the old creative failed.
• Risky: “Agencies didn’t get us” with no detail on what was asked or measured.

This question also surfaces whether “more marketing” is the wrong ask. If prior spend increased traffic without improving activation, repeating spend is not bravery. It is amnesia with a budget line.

Question 3: who decides, and how quickly can we ship?

Strategy work dies in slow decision systems. If every headline needs seven stakeholders and a board aesthetic preference, we will produce decks, not learning. I ask who the DRI is, how design/engineering/marketing coordinate, and what “ship this week” means in practice.

Stripe- and Linear-like operating cultures-small teams, clear owners, high craft bar-can move fast without chaos. Not every client needs to be them. They do need a path from insight to live change measured in days or a couple of weeks, not quarters.

Red flags: invisible founders who “will review later,” legal as a surprise final boss for every sentence, or a redesign committee that cannot cut a nav item. Green flags: a founder or CPO who can say yes, a designer/engineer pair ready to implement, and analytics access without a scavenger hunt.

I would rather work with a sharp team that ships imperfectly every week than a prestigious brand that polishes a wrong message for a quarter.

Question 4: are you open to cutting?

Clarity work is mostly subtraction. Features, channels, claims, nav items, CTAs-someone’s favourite thing usually has to go. If the answer is “we can add, but we can’t remove,” we are negotiating decoration.

This is where the hidden cost of features nobody asked for becomes personal. Cutting is emotional. I respect that. I also need permission to recommend it. Apple’s product pages look inevitable because of what they omit. Most startup pages look anxious because they omit nothing.

Question 5: what does success look like in 30 and 90 days?

Vague success (“stronger brand,” “more modern,” “buzz”) guarantees disputed endings. I want behavioural markers: activation rate, demo quality, time-to-first-value, unqualified lead reduction, retention after week one. Directionally right beats fake precision.

For teams who want a compressed operating plan, what I would change in 30 days and if I joined tomorrow show the level of concreteness I aim for.

Additional filters I quietly use

Integrity of the problem

I look for problems worth solving for real customers-not growth theatre. Whether a product is worth building is a question I ask myself as much as clients. If the product is fundamentally unwanted, a prettier funnel is not kindness.

Respect for evidence

We do not need a research department. We do need willingness to watch users, read support tickets, and treat NN/g-style observation as more persuasive than the loudest opinion in the room.

Scope honesty

“Rebuild the brand, website, product, and growth engine in six weeks” is not ambition. It is a scheduling hallucination. I would rather narrow scope and leave a system behind-see systems over campaigns-than promise a transformation montage.

How the first conversation usually runs

I do not send a fifty-question form and call it discovery. We talk. I ask the five questions in plain language, listen for specifics, and mirror back what I think the constraint is. If we disagree about the constraint, that disagreement is valuable-better now than after a redesign kick-off.

1. They describe the symptom (leads, bounce, “need marketing”).
2. I ask which customer decision is stuck.
3. We walk prior attempts without blame.
4. We map decision rights and shipping reality.
5. We draft 30/90-day success markers live.
6. I say yes, propose a clarity sprint, or recommend waiting.

Sometimes founders expect a pitch deck about deliverables. I would rather be slightly awkward and precise. Polite ambiguity is how projects become expensive calendars. If you want a sense of how I prioritise once inside, if I joined your startup tomorrow is the operating flavour-not a bait-and-switch into endless workshops.

Red-flag phrases (and what I ask next)

None of these phrases are automatic disqualifiers. They are smoke. The follow-up finds whether there is fire-or just a team that has not been asked hard questions kindly enough.

What “good collaboration” looks like after yes

Fit questions are not only a gate. They set norms. After yes, I expect: shared access to analytics and support themes, a weekly decision slot, permission to challenge sacred copy, and honesty when experiments fail. In return, founders should expect plain recommendations, written tradeoffs, and no theatre metrics.

• We document the customer decision and success markers in week one.
• We ship narrative and path changes before channel experiments when clarity is the constraint.
• We keep a cut list alongside the build list.
• We review behaviour, not opinions, in the weekly slot.

This pairs with systems over campaigns and strategy to launch. The client-fit bar exists so those methods can work. Without decision speed and cutting permission, even a perfect framework becomes slides.

What happens when answers are unclear

Unclear answers are not an automatic no. Sometimes they are the brief. We start with a short clarity engagement: ICP, job, narrative, success metrics. Then we decide whether to continue into experience work.

Automatic pauses look more like this: no decision owner, refusal to measure, insistence that the only problem is “awareness,” or a request to manufacture urgency for a product the team does not believe in. Waiting is underrated. So is saying no early-before invoices create false commitment.

A worked example: two founders, two answers

Founder A wants a “world-class site.” Answers: decision = more demos; tried paid ads (traffic up, demos flat); CPO decides weekly; open to cutting features; 90-day success = higher qualified demo rate and clearer pricing conversations. Fit: yes-likely a clarity and path problem.

Founder B wants “aggressive growth marketing.” Answers: decision = unclear; tried “a bit of everything”; approvals involve four stakeholders across time zones; nothing can be removed because investors liked the feature list; success = “be everywhere.” Fit: not yet. Recommend internal alignment first, or a tiny narrative sprint with one owner.

Same category, different readiness. The questions revealed it in thirty minutes-cheaper than a three-month polite failure.

How to use this list as a founder

1. Answer the five questions in writing before you shop for help.
2. Share them in the first call; notice who engages vs who dodges.
3. Assign a DRI for decisions before kick-off.
4. Agree 30- and 90-day markers and how you’ll review them.
5. Give explicit permission to recommend cuts.

If those answers are clear, we can do sharp work. If not, we create that clarity together-or we wait. For a deeper diagnostic when everything “looks like a marketing problem,” read every startup looks like a marketing problem until you dig deeper.