3 Simple Questions That Close Deals

Now, I’m a straightforward guy. Over the years, I’ve learned that keeping it simple and to the point gets you further than all the fancy talk in the world. When I’m looking at a deal—whether it's closing a sale, making an investment, or pitching to a client—I always start by asking myself what I call the 3 Whys. They’ve guided me through plenty of wins, from small businesses to multi-million-pound deals.

Here they are:

Why Change?

You need to get to the heart of why the customer’s thinking of shaking things up. What’s the pain that’s pushing them to make a move? Maybe they’re tired of poor service or the competition’s nipping at their heels. If you don’t know why they’re considering change, you’re already out of the game.

Example: “What’s making you think about a new solution? What’s no’ working with your current setup?”

Why Now?

Timing, as we say, is everything. Knowing why the customer needs to act now—why they’re feeling the heat—gives you a proper insight into their urgency. Maybe the year-end targets are looming, or there’s a new player in their market. Whatever it is, you need to know what’s got them on the clock.

Example: “What’s happened recently that’s making this a priority now?”

Why Us?

This one’s my favourite because it cuts right to the chase. After you’ve got a good feel for why they’re looking to make a change and why it’s urgent, you’ve got to get them talking about why they reckon you’re the right choice. If they can’t tell you why your solution fits, you’ve got some graft ahead. But if they can? You’re on to a winner.

Example: “What is it about us that makes you think we’re the right partner for this?”

Now, these three questions have been with me through thick and thin. They’re the reason I’ve been able to close deals from Glasgow to Beijing. But it’s not just about asking the questions—you’ve got to know how to sell, and not in a way that comes across like a double-glazing salesman in the 90s. This is where the Value Sales Method comes in.

What is the Value Sales Method?

Let me tell you something that’s as true in Edinburgh as it is in New York—customers today are savvy. They don’t fall for the hard sell anymore. They’ve done their homework, and they’ve probably seen a pitch or two before yours. So, if you’re still trying to push your product like it’s a late-night shopping channel, you’re going to struggle.

The Value Sales Method flips that on its head. It’s all about shifting the focus away from what you’re selling and zeroing in on solving the customer’s problem.

You’ve got to show them that you understand their pain and that your solution is what they need—simple as that.

Here’s what it looks like in practice:

Consultative Selling:

You’re not there to rattle off product features like a machine gun. Your job is to sit down, ask smart questions, and really understand what’s giving the client grief.

Storytelling:

I'm a Scot and we're great storytellers, right? Well, it works in sales too. Don’t just throw numbers and facts at them—build a story around how your product fits into their world and how it’s going to make their life easier. That’s what they’ll remember.

Confidence:

Now, I’m no fan of the loud, shouty types. The best salespeople are calm, collected, and speak with the kind of confidence that makes you sit up and listen. They know their stuff, and more importantly, they know how to explain it clearly.

The 3 Whys + Value Sales Method: A Powerful Combo

When you mix the 3 Whys with the Value Sales Method, you’ve got a winning formula that works every time. It’s about digging deep into the customer’s world, finding out what makes them tick, and positioning yourself as the solution they need. Trust me—this approach works across the Globe.

Here’s how it plays out:

You Listen First: The 3 Whys are all about asking the right questions. You’re there to listen first, not pitch. When the customer opens up about their pain points, you’re already halfway there.

You Tailor Your Approach: Once you’ve heard their answers, you can craft your solution to fit like a glove. You’re no longer just offering a product; you’re offering the right solution at the right time.

That’s where the Value Sales Method kicks in.

You Close With Confidence: When you know why they need change, why it’s urgent, and why they’re picking you, you’ve got the confidence to close the deal. By then, the customer already sees the value you bring, and it’s more about when, not if, they sign on the dotted line.

Why It Works: Tried and Tested

After decades in the game, I can tell you one thing for sure—this approach is solid. I’ve seen it boost sales teams, close deals, and grow businesses, no matter the industry.

Here are some benefits I’ve seen again and again:

Stronger Relationships: People buy from people they trust. If you’ve taken the time to understand their pain, they’ll trust you to solve it.

Higher Close Rates: By focusing on value, not features, you’re aligning yourself with the customer’s real needs. The result? More deals close, and faster.

Better Team Performance: Teams that use the Value Sales Method are more confident and better prepared. And when they’re prepared, they’re more successful.

Final Thoughts from a Seasoned Entrepreneur

After building, selling, and investing in businesses for decades, one thing’s crystal clear—success in sales comes down to this: understanding your customer. It’s not about slick presentations or fancy charts. It’s about listening to their needs, solving their problems, and delivering value.

Before you head into your next big meeting, ask yourself the 3 Whys. If you can answer those, you’re well on your way to closing the deal.

Combine that with the Value Sales Method, and not only will you close more deals, but you’ll build relationships that last a lifetime.

And remember, whether you’re pitching in Glasgow or Beijing—people are the same everywhere. They don’t want to be sold to. They want to be understood.

David is a partner at Tollejo who help connect boardrooms to customers