The wrong question

The wrong question in commercial leadership is any question that treats a customer problem as a seller execution problem. It frames the challenge as a matter of technique, activity, or process, when the real question is: why would this customer change anything at all? The distinction determines what you prepare, what you ask, and whether the conversation produces movement.

It is a question I have heard from sales leaders more times than I can count: how do we get our sellers to perform better? It is a reasonable question. It is also, in most cases, the wrong one.

Not because performance does not matter. It does. But because performance is an outcome, not a starting point. Before you can improve how your sellers operate, you need to answer something more fundamental: why would a customer in their position actually want to change anything at all?

That question is harder. It requires real knowledge of the customer's world, the kind that a well-structured discovery conversation is designed to surface. It requires preparation. Most organisations never ask it. And so their commercial conversations stall, not because their sellers lack technique, but because nobody has created a reason for the customer to move.

I have asked myself this question often enough, from both sides of the conversation. In retail environments where I worked with young commercial teams, the most common failure was not confidence or product knowledge. It was the absence of a genuine perspective on the customer's situation before walking into the room. The sellers who stood out were not the most assertive ones. They were the ones who had thought carefully about why this customer, in this moment, might actually want to change something.

The question is worth sitting with: if you had to explain why a customer should change their current approach, using only facts about their situation and not the features of your solution, could you do it? Most cannot. And that gap is where commercial conversations go quiet.

01

Two versions of Why: and why they are not the same

There are two ways to apply the concept of Why in commercial work, and confusing them is one of the most consistent sources of commercial underperformance in B2B organisations.

The first is internal. Why does our organisation exist? What is our purpose? What are we trying to communicate about who we are and what we stand for? This is a legitimate question, and the clarity it produces has real value for positioning, messaging, and internal alignment. Many organisations invest significantly in answering it.

The second is external. Why would this specific customer change their current approach? What in their situation makes the cost of staying still greater than the risk of acting? What has shifted that makes this conversation relevant now rather than next year? These are genuinely different questions, and they require genuinely different preparation. McKinsey's research on how B2B companies talk past their customers found exactly this: the themes suppliers emphasise most heavily in their positioning, such as sustainability, global reach, and social responsibility, rank among the least influential factors in how customers actually evaluate them.

What most organisations invest in is answering the internal version. What most commercial conversations require is the external one. That gap is not a messaging problem. It is a thinking problem, and it sits upstream of everything else.

In the commercial conversation, the circle that matters most is the customer's. Not your Why, but theirs. Why would they change the way they currently operate? Why is the status quo not good enough? Why should they act now, rather than wait, or do nothing at all?

If you cannot answer those questions before you walk into the room, you are not ready to have the conversation.

02

What customers actually decide

Every buying decision is fundamentally a decision about the customer's situation, not the seller's solution.

Customers do not change because you described your product well. They change because something shifted in their understanding of their own situation. The best commercial conversations do not begin with "let me tell you about what we do." They begin with something the customer had not fully considered about where they are.

This is not a technique. It is a different purpose for the commercial conversation entirely. The seller who leads with product is trying to create interest. The seller who leads with insight is trying to create movement. Those are not the same thing, and they require very different preparation.

This is the core of the Challenger approach: the most effective sellers in complex B2B environments are not those with the best relationships or the most persistence. They are the ones who teach the customer something genuinely new about their own world. They enter every significant conversation with a perspective, not just a presentation.

I recognise this distinction from having been on both sides of it. As a seller, the temptation is to present the best version of your offer and trust that the customer will connect it to their own needs. As someone helping organisations clarify their commercial thinking, I have seen how rarely that connection happens automatically. Customers are busy. They do not do the analytical work of linking your solution to their situation. That work belongs to the seller, and it has to happen before the conversation, not during it.

03

The three capabilities that create movement

Most sellers know what they sell. That knowledge is well developed, rehearsed, and easy to deploy. What is far less developed is knowledge of the customer's world at a depth that makes genuine insight possible.

To teach a customer something they have not considered, you need to understand their industry better than they expected you to. You need to know what the forward-looking pressures in their market are. You need to have formed a view about how those pressures will affect their specific position, and you need to be able to articulate that view in a way that is relevant to the person sitting across from you.

That requires three distinct capabilities, all of which must be present before the conversation begins.

I know this gap from idretten as well as from selling. In sports, the preparation before competition determines what is available in the moment. You cannot improvise technique under pressure that you have not built through deliberate practice. Commercial preparation works the same way: the insight you can deliver with confidence in a meeting is the one you built, tested, and sharpened before you walked in. Improvised insight is just opinion.

The third component is the most misunderstood. Constructive tension is not about disagreement for its own sake, or correcting the customer's assumptions in a way that creates friction. It is about having the courage to say something the customer had not fully considered, even before the relationship gives you permission. That requires more than knowledge. It requires a genuine perspective, and the confidence to hold it under the polite deflection that often follows.

Most organisations invest heavily in the first capability and ignore the second and third entirely. The result is sellers who are well-informed but unable to create movement, because information without relevance and without tension is presentation, not insight.

04

Where conversations actually stall

Conversations that end in stalemate were not lost at close. They were lost earlier, when the customer's reason to change was never established.

When a commercial conversation ends in a price negotiation, or in a polite "we'll be in touch," the most common diagnosis is poor closing technique. That diagnosis is almost always wrong.

Conversations stall because the customer's Why was never established. The seller presented a What. The customer evaluated it against alternatives. Without a clear understanding of why their current situation is insufficient, they have no internal pressure to act. And so they compare, delay, or default to whoever they already know.

I have watched this happen in commercial teams I have worked with closely. The seller leaves the meeting confident. It went well. The customer was engaged, asked good questions, seemed interested. And then the silence. Not because the meeting was bad. Because the customer left without a clear internal reason to act. There was no insight that made their current situation feel insufficient. Nothing that made the cost of staying still visible.

This is where the value equation matters most. Price becomes the battleground when value has not been established upstream. And value cannot be established upstream if the seller has not first helped the customer articulate their own reason to change.

The customer's Why is not just a sales concept. It is the precondition for the entire commercial conversation to have meaning.

05

The question worth asking

If you want your commercial conversations to move differently, the starting point is not "how do we get our sellers to perform better?" It is this: what does a customer need to understand about their own situation before our solution becomes genuinely relevant to them?

That is a harder question. It requires real knowledge of the customer's world. It requires preparation that most organisations do not build into their commercial processes. It requires the confidence to bring a perspective into a conversation before the relationship gives you permission.

But it is the only question that leads to a conversation worth having.

Because when the customer's Why is clear, the rest follows. How you solve it, what you specifically offer, the price you charge. These become details in service of a decision that has already, in the customer's mind, been made.

That is not the end of the commercial conversation. It is where the real one begins.

Frequently asked questions

What is the wrong question most commercial teams ask?

The wrong question is: how do we get our sellers to perform better? It assumes execution is the problem. The right question is: what does a customer need to understand about their own situation before our solution becomes genuinely relevant to them? That question changes the entire structure of how you prepare for and conduct commercial conversations.

What is Jobs to Be Done and why does it matter for B2B selling?

Jobs to Be Done, developed by Clayton Christensen, asks what a customer is actually trying to accomplish when they make a purchase decision. In B2B selling, it shifts attention from what a product does to what problem the customer is genuinely trying to solve, and why they need to solve it now.

What makes a commercial question genuinely insight-led?

Insight-led questions connect what you know about the customer's industry or situation to implications they may not have fully considered. They come from preparation and genuine curiosity, not from a script. The best ones make the customer pause before responding. That is usually a sign you have reached something real.