The Five Questions I Ask Every New Client

Most people arrive with a stated problem. The real problem is usually one level back from that. These five questions are how I find it — and how you can start to find it yourself, before we've even spoken.

1. "If everything went right this year — what would have changed?"

This is the first question, and it reframes everything that follows. Most people arrive telling me what they're working on. This question asks not what they're doing, but what they're trying to produce. The gap between the two is usually where the real work is.

Someone who can answer it immediately — clearly, specifically — is in a very different place from someone who pauses, qualifies, or gives me a list of things they'd like to happen. Both are fine. But they need different things, and knowing which one I'm talking to shapes everything else.

The question also cuts through activity. You can be extremely busy and still not be moving toward anything in particular. This question finds that out in about thirty seconds.

2. "What's actually in the way — not the first answer, the real one?"

The stated obstacle is almost never the real obstacle.

"We need more customers" is a stated obstacle. "We can't explain what we do clearly enough to convert the customers we already talk to" is the real one. "We need funding" is a stated obstacle. "Our case for the project hasn't been built from the funder's criteria backwards" is the real one.

I always ask for the second answer explicitly, because the first one arrives without prompting. The second one requires a bit of pressure — not much, just enough to move past the comfortable version of the problem and get to the one that's actually worth solving.

3. "Can you explain what you do in two sentences — the way you'd say it to someone you just met?"

I ask this one without warning. If they can answer it cleanly — confidently, in plain language, without backtracking — we move on. If they pause, qualify, start three different sentences, or give me five sentences that don't quite land, that tells me something important.

A surprising number of people who have been running their business for years cannot do this cleanly. Not because they don't know what they do. Because they've never had to distil it into something that works on a stranger. They know the whole of it — the nuance, the context, the history — and they can't find the version that fits in a thirty-second window.

That gap between what a business does and what it can say about itself is expensive. Every pitch, every referral conversation, every proposal takes longer than it should. The work is real — the story isn't there yet.

4. "Before you commit to this — what would have to be true for it to work?"

This is the most revealing question of the five. It forces the articulation of assumptions — usually assumptions that haven't been written down or tested against anything.

Every plan is built on assumptions. The question is whether those assumptions have been examined. Most haven't, not because the person isn't capable, but because examining them properly requires a kind of honesty that's uncomfortable when you're also trying to stay motivated about something.

When I ask this question, two or three things almost always come up that the person hasn't properly addressed. Occasionally everything comes up — and that's a different conversation, but also a more important one. Finding out that the foundations need work before the money goes in is always better than finding out afterwards.

I spent a long time in construction watching projects where this question had never been asked. The warning signs were nearly always there. They just weren't visible to someone standing too close to it.

5. "If nothing changed for six months — what happens?"

This isn't asked to create urgency artificially. It's asked to understand the real cost of not acting.

Some problems are comfortable enough to live with indefinitely. They're worth fixing, but they're not urgent, and pretending otherwise would be dishonest. Others are quietly getting more expensive — in money, in time, in options closing off — and the person hasn't quite let themselves acknowledge how much.

Saying it out loud is sometimes the most useful thing that happens in the whole conversation. Not because I've told them anything they didn't already know. Because the question made them say it clearly, probably for the first time.

What these questions have in common

None of them are trick questions. None of them are designed to catch someone out. They're designed to find out where the actual problem is — because a good diagnosis is worth more than a good plan built on the wrong problem.

The most common outcome of a first conversation is that we end up talking about something different from what we started with. Not because I've redirected anything deliberately. Because the right questions found the right problem — and it turned out to be one level back from where the person had been looking.

That's what a good first conversation is for. And it's available to anyone willing to ask themselves the same questions honestly, before they speak to anyone else.