The Secret to Selling? Just Have a Proper Chat

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On Having a Natter, and Why It Might Just Be the Secret to Everything

The Secret to Selling? Just Have a Proper Chat

On Having a Natter, and Why It Might Just Be the Secret to Everything

Now, look. It’s a funny old thing, the world of business. We’ve spent the last twenty years inventing ever more complicated ways to avoid actually speaking to one another. You want to change your gas bill, you have to navigate a labyrinth of button-pressing choices, only to be cut off by a robot with the warmth of a broken freezer. Buying a new sofa online? A pop-up will instantly demand your email address with all the subtlety of a burglar.

It’s all a bit… barmy, isn’t it? We’re so busy ‘optimising funnels’ and ‘leveraging assets’ that we’ve forgotten the most powerful tool we ever had: a decent chat.

And that, in a nutshell, is what this new-fangled thing called ‘conversational selling’ is all about. Which, as is often the case with clever business terms, is just a fancy way of describing a bit of good, old-fashioned common sense. It’s the simple, rather lovely idea that the best way to sell something to someone is to have a nice, helpful conversation with them first.

Revolutionary, I know. Shall we give it a whirl?


The Secret Ingredient of Selling? Just a Bit of Human Decency

At its heart, this is all wonderfully simple. It’s about remembering there’s a person on the other end of the line or the chat window. A person who, like you or I, probably just wants to solve a problem with the minimum of fuss.

For Goodness’ Sake, Let Them Get a Word In

Remember those dreadful salespeople who talk at you for ten minutes solid? The sort of monologue that makes you want to fake your own death and move to a small, uncontactable island. The first rule here is simply to listen.

But “listening” isn’t just being quiet; it’s an active, strategic skill. It’s about asking “proper questions” and then proving you heard the answer.

Technique 1: Ask “Open” Questions, Not “Closed” Ones A “closed” question can only be answered with a “yes” or “no” (e.g., “Are you happy with your current setup?”). It’s a conversational dead end. An “open” question invites a story.

  • Closed (Bad): “Is your current software slow?”

  • Open (Good): “What’s your experience been like with your current software?”

Technique 2: Be a “Doctor,” Not a “Pitch-Bot” Your first job isn’t to pitch; it’s to diagnose. Don’t lead with your solution. Ask questions that uncover a problem or “pain point.”

Take Chris, who was trying to sell cloud software to a small chain of cafés. The owner was clearly bracing for a hard sell. But Chris used a perfect diagnostic question—“What’s the one thing that slows your team down most?”—and just listened.

Here are some other “pain-hunting” questions:

  • “What’s the most frustrating part of your [process] right now?”

  • “If you could wave a magic wand and fix one thing about your current setup, what would it be?”

  • “Walk me through what happens when [X] goes wrong.”

Technique 3: “Loop” Their Answer Before you ever mention your product, you must prove you heard them. Summarize their problem back to them in your own words.

  • The Customer: “The main issue is that our current gadget keeps overheating, and my team says it’s clunky.”

  • Bad Response (Pitch-Bot): “Well, my product is fast and never overheats!” (You sound like you were just waiting to talk).

  • Good Response (Looping): “Okay, so if I’m hearing you right, the main issues aren’t about price. It’s that the current unit is overheating and, just as importantly, it’s clunky and frustrating the team. Is that about right?”

When they say “Yes, that’s it exactly,” you have just built more trust than any sales pitch could.

Be a Pal, Not a Pitch-Bot

Nobody likes being ‘sold to’, but everyone appreciates a bit of help from someone they trust. The goal isn’t to ram a product down someone’s throat. It’s to build a little bit of rapport, to show them you’re a reasonable human being who understands their problem.

Technique 1: Find a Genuine “Non-Work” Connection Rapport isn’t about a fake smile; it’s about finding a moment of genuine human connection. Before you dive into business, find a way to be a person, not a salesperson.

  • How to do it: Look for clues. In a video call, do they have a guitar on the wall? A dog in the background? A favourite team’s mug on their desk?

  • Example:

    • Pitch-Bot: “Okay, let’s start. My first question is about your Q3 budget…”

    • A Pal: “Before we start, I have to ask—is that a Martin guitar behind you? I play a little myself…”

Technique 2: Be a “Helpful Expert,” Not a “Closer” A “Closer” needs to sell their product. A “Helpful Expert” wants to solve the customer’s problem, even if the solution isn’t theirs. This is the ultimate trust-builder.

  • How to do it: Be the one person who gives them an honest assessment.

  • Example:

    • Customer: “I need a system that does X, Y, and Z.”

    • A Pal: “That’s helpful. My system is world-class at X and Y, but I’ll be honest, Z isn’t our strongest feature. If Z is your most important need, you might be better off looking at [Competitor’s Name]. If you’re more focused on X and Y, we’re the best fit.”

You may “lose” that one sale, but you have just become the most trustworthy expert in your field. They will come back to you for everything else and send all their friends your way.

One Size Fits Nobody

We’ve all had those lazy emails. The joy of a “proper chat” is that it gives you all the clues you need to make your pitch personal. Your customer just told you exactly what they care about. Use that information!

Technique: Use Their Own Words (The “Echo Method”) The most effective sales pitch isn’t a pre-written script; it’s a direct response to the problems they just told you about. Actively “echo” their specific words and priorities back to them.

  • The Customer: “The main issue is that my team is just exhausted. They’re burned out from all the manual data entry.”

  • Bad (Scripted Pitch): “Well, our product has a robust, synergistic, multi-platform architecture…” (This is gobbledygook).

  • Good (Echoing Their Words): “I’m glad you brought that up, because that’s exactly what we’re built for. Let me show you how this dashboard will eliminate that manual data entry for you. The main goal here is to get your exhausted team their time back.”

Figure it Out Together

Instead of presenting yourself as the genius with all the answers, position yourself as a helpful collaborator. A simple ‘Well, let’s see… what if we tried this?’ makes the other person feel part of the solution.

Technique 1: Use “Collaborative Language” Swap out “I” and “you” for “we” and “us.” This simple language shift changes the entire dynamic from a pitch to a partnership.

  • Before (Pitching):I have a solution that you need. I think you should buy this.”

  • After (Collaborating):What if we tried to sketch out a solution? Let’s see if we can find a way to fix this.”

Technique 2: The “Virtual Whiteboard” Don’t just describe your solution; build it with them. When you “sketch” the solution together (even if it’s just verbally), they develop a sense of ownership.

One chap I know sells home office furniture. A client rang up, frustrated by a desk that looked lovely online but didn’t fit their awkward loft space. Instead of sending over alternatives, he got out a tape measure, asked them to send a photo, and spent fifteen minutes helping sketch out the perfect setup. He wasn’t selling a desk; he was solving an “awkward loft” problem. They ordered the whole lot the next day, and he got three referrals that same week.


So, What’s in It for You? (Apart from a Clearer Conscience)

This all sounds very nice and cosy. I hear you cry, but does it actually work? Well, it seems so. And the reasons are, again, disarmingly simple.

  • People Will Actually Like You. When you treat people with respect and genuinely help them, they tend to be rather pleased about it. They feel good about the experience, and they feel good about your company. And chuffed customers, as we all know, are the best kind.

  • You’ll Stop Wasting Time. By having a proper chat early on, you can quickly work out if you’ve got the right thing for them. No more six-week email chains only to discover they needed the blue one, not the red one. It’s efficient.

  • They’ll Keep Coming Back. You know that little coffee shop where they remember your name? You go back there, don’t you? This is the same idea. A good conversation builds a relationship, and relationships are what keep people loyal, long after the thrill of a 10% discount has faded.

  • You Get All the Best Gossip. People will tell you all sorts in a friendly chat. What they love, what they hate, what their competitor is up to. It’s market research, but without the clipboards and the fluorescent lighting. It’s gold dust.

And There We Have It.

When you strip it all back, ‘conversational selling’ isn’t a sales strategy. It’s a life strategy. It’s about being curious, being helpful, and being human. It’s about realising that the shortest distance between a problem and a solution is, more often than not, a good, honest conversation.

In a world that’s getting faster and more automated, slowing down for a moment to have a proper natter might just be the most revolutionary thing you can do. And certainly the most pleasant. Now, who’s putting the kettle on?


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