A few days ago I posted a story from some years back, about a car salesman who lost a sale in three seconds.
He took one look at me (bloke, kids in tow) and decided I wanted something sensible with good boot space. He never asked. If he had, he'd have discovered my first criterion for a car is that it goes vroom.
The response told me it hit a nerve. Plenty of people recognised the salesman. Rather fewer, I suspect, recognised themselves.
And it wasn't even my worst showroom story.
Years ago I went with someone while she bought a car. She'd done all the research, knew the exact model she wanted and was ready to buy that day. The easiest sale that dealership was ever going to make.
Except the salesman spent the entire conversation talking to me.
I wasn't buying a car. She was. So she took her money to another dealership and switched brands completely. She never went back to that manufacturer again.
The first salesman assumed what I wanted. The second assumed who was buying. Both assumptions killed the sale. But the second one cost the manufacturer a customer for life.
Both of those showrooms are a long time in the past. I still see the same assumptions every week, dressed up in websites, proposals and marketing copy instead of a showroom smile.
My point in that post was simple. People open their wallets the moment they feel understood by you. Most businesses work hard at the opposite, getting the customer to understand them, in their marketing, their websites, their sales conversations and their proposals.
The mistake almost everyone makes
Look at the average website, brochure or sales pitch and you'll find a business working incredibly hard to be understood. It leads with:
- Our process: the five stages, the methodology, the clever framework
- Our credentials: years in business, awards, qualifications, logos
- Our features: everything the product or service includes
- Our story: how it all started and why we care so much about it
None of this is wrong. But notice the direction of travel. It's all aimed at getting the customer to understand us.
Meanwhile your prospect is sitting there asking a much more selfish question: does this person get my situation?
The moment the answer is yes, everything changes. Until then, you're just noise.
Why feeling understood is what opens the wallet
Think about the last significant purchase you made. I don't mean the chocolate by the till. Something that mattered.
Nobody decides those on the spot. We research. We compare. We look people up. Long before we speak to anyone, we're quietly auditioning them.
And what are we actually looking for during all that homework? Three things:
- Recognition: “They're describing my exact problem, in my words.”
- Relevance: “They've clearly helped people like me before.”
- Reassurance: “They understand what's at stake for me if this goes wrong, and what it would cost me, personally, to get it wrong.”
Notice that not one of those is “I fully understand their methodology.” That comes later, if at all. People buy the feeling of being understood first and rationalise the details afterwards.
This is also why the businesses that shout the loudest often convert the worst.
The questions that do the selling for you
So how do you make someone feel understood? You ask, and you actually listen.
Simple to say. Everyone nods along to “ask good questions” and almost nobody gives it a structure. These are the questions I'd want answered in any sales conversation, roughly in this order:
- What are you actually trying to achieve? The outcome behind the product they think they need.
- What's prompted this now? Something always has. That something is the real driver of the sale.
- What have you already tried? This tells you what they believe, what they're sceptical of and what's burned them before.
- What happens if nothing changes? The cost of doing nothing is often the strongest motivator they have. Let them say it out loud.
- What does success look like for them? Their words, their measures, their picture of sorted.
- What matters most about how this gets done? Speed? Certainty? Being kept informed? Not looking foolish to their board or their partner?
Ask those six and something interesting happens. You barely need to pitch. You simply play back what you've heard and show how you get them there.
They've told you exactly what to sell them. And by feeling heard, they've already started to trust you.
Making people feel understood before you ever meet them
Most of your future customers will research you long before they talk to you. Your marketing has one job during that phase: make a stranger feel understood.
A few ways to do that:
- Answer the questions nobody in your industry will answer. Especially pricing. Your competitors already know roughly what you charge. The only people you're hiding it from are your customers. Even a range, with an honest explanation of what moves the price, builds more trust than silence.
- Turn every sales question into content. Every question a real prospect asks you is proof of something your market wants to know. Answer it publicly, in plain English and you're building trust at scale while your competitors keep it behind a “book a call” button.
- Show up consistently. Sporadic posting says unreliable. Regular, useful content says this person lives and breathes my problem. A prospect should read it and think “that's me” before they ever think “that's clever.”
- Use what you know about people. If you hold a list, segment it. The garage that knows which customers love fast cars and which love practical ones, and only sends each group the content they'd care about, makes every message feel personal. Same effort, completely different feeling on the receiving end.
A simple test for everything you put out
Before your next email, post, proposal or pitch goes out the door, ask one question:
Is this trying to make them understand me, or helping them feel understood by me?
If the first three sentences are about you, your business or your process, you've got it backwards. Flip it. Start with their situation, their frustration, their ambition. Then earn the right to talk about yourself.
It sounds like a small shift. In practice it changes what you write, what you ask and what you lead with in the room. And people rarely walk away from someone who really gets them.
That salesman had three seconds and spent them deciding who I was.
What he could have done in those same three seconds is open his mouth and ask.
Right now, somewhere, a prospect is giving your business its three seconds. On your website, in your content, across the table. Would they say you get them?




