Challenging Questions Sell

Challenging Questions Sell

Focus on opening the prospect’s mind with challenging questions rather than closing a sale.


It’s ironic, but the way to close on sales is to focus on something else. It’s a bit like seeking a blessing. Blessing comes from something other than the blessing itself. If you strive to achieve it, then you’ll never get it.

And sales are a bit like that, too.

If you make it your goal to sell your product or service to a particular prospect, and you focus on that objective more than anything else, then it won’t happen. The prospect will know that that’s all you care about. And no one is going to buy from on that basis.


Why do salespeople focus on the wrong thing?

Sales people know this from their own experience; so why is it that the habitually focus on the wrong thing?

The reason is that the reward system where they’re employed it drives their compensation; and selling gives them job satisfaction. The two are connected. If they’re not selling - if they’re not making sales - then they feel that they’re failing to do their job.

That means that in order to focus on the right thing, they and their sales managers must redefine what it means to be successful.

Some years ago, and this may still be true today, one of the criteria that managers at Royal Bank of Scotland were rated on was their ability to work as a team member. Maybe that’s something that you do in your organisation; but here’s what set them apart: Even if managers reached their targets, if they failed to function as they were expected to within their team, they received a lower rating.

It’s an oft-repeated truth among psychologists that you get the behaviour that you reinforce. If success is measured by sales, then that’s what people will focus on. And they’ll do whatever it takes to make them. Some salespeople are less ethical than others.

But the problem isn’t limited to how you define success. Salespeople also get a buzz out of the chase. And so that means that you also must help them to find a way to make the chase consistent with pursuing the right thing.


What’s the right thing to focus on?

The right thing to focus on is the prospect’s needs, not what the supplier sells.

When you focus on what you sell, then the tendency is to boast about how great your product or service is; but when you focus on the needs of the prospect, then you’re more interested in finding a way to solve the problems that they’re having.

Some years ago, a book was published called Solution Selling. It outlined the need to help prospects see themselves using the seller’s products or services as a means to solve their problems.

Prospects are looking for solutions. They’re considering a number of options. Yours is one of them. Your job is to help them to understand which of the options will solve their problem best. Of course, you hope that you’ll be able to demonstrate that your product is better than any of the others on offer, but it should be evident that your primary goal is to help them find the best one for them.


How do you do that?

By asking challenging questions.

Before we get to the questions themselves, however, it’s worth thinking about how salespeople can know that they need to ask them, or that they need to ask more of them.


What evidence is there that salespeople need to ask challenging questions?

There are a few tell-tale signs that salespeople need to ask challenging questions.


You’re doing most of the talking

One way you’ll know that you need to ask challenging questions is that you’re doing most of the talking.

Salespeople have earned a reputation for the “gift of the gab”. The thing is that when you’re busy “gabbing”, you’re not listening; and salespeople need to learn how to do that even better.

You can’t listen to what someone else says unless you stop talking, because unlike Any Questions? Prospects won’t compete with you for air time. So if you’re talking most of the time, then there’s no chance that you can learn anything from the other person.


Your prospects don’t respond to your questions

Talk show hosts know this.

They try to lead the person they’re interviewing by asking questions. But some people need to be led more than others. That doesn’t mean putting words in their mouths or finishing their sentences for them. Instead, it means asking them those questions that they’re most likely to answer even as you lead them to the more challenging ones.

If you’re getting answers that don’t tell you much, like the worst interview that Parky ever did, then it means that you need to adopt an approach that will get your prospects to talk to you.


Your prospects don’t ask you anything about your product

There’s a third way that you’ll know that you need to ask challenging questions, and that’s the absence of questions from your prospects about how your product could help them.

A rule of writing is to show; not tell. You don’t tell your readers how excited they should be, for instance. Instead you describe a situation that will make them excited.

When you ask challenging questions, then you’re doing exactly the same thing. You’re causing your prospects to think about what they need in a way that challenges them; that pulls them out of their proverbial comfort zone. Done properly, they’ll feel an intrinsic excitement as your questions lead them toward a solution.


Your prospects are distracted

The fourth way that you’ll know that you need to ask challenging questions is that your prospects seem distracted. When people get bored, they’re more easily distracted.

They might look at their watch or pick up their phone. They may start looking at other things in the room, or other people as they pass by. Of course, you hope that this will never happen; but it will if you don’t keep them engaged in the conversation.

Remember that making sales calls is your job. It’s not the job of prospects to attend them. They’re giving you some of their very valuable time to meet with you. Don’t bore them. Engage them.


What questions will challenge prospects?

What questions can you ask that will challenge prospects? They’re the ones that they don’t expect. They’re the ones that they have to think about.

For instance, average salespeople might ask what the problem is that their prospects have, and that certainly sounds reasonable. But suppose you prefaced your question by asking instead what results they wanted compared to what they’re getting.

When you do that, you combine ideas. You also stir up their pain, which adds urgency to the need they feel to find a solution.

You could ask them what their organisation is unable to do as a result, what the lost opportunity cost is, how many people are affected by it, and how long those people have been distracted by it. It’s common for managers to avoid dealing with problems they don’t like, and so the more you can stir things up, the better for both of you.

But notice that when you do it like that, that you’re reminding them of how it makes them feel; not by telling them how great your product is.

The other thing is that when you ask them how much the problem has cost the organisation thus far, it helps to frame the cost of your product, as well. It’s the cost of maintaining the status quo over some period of time compared to solving it right now, not simply the price of the solution.

Then you can switch gears. You could ask them how it would feel if they solved it. That creates hope.

You know that this to be true of yourself: People buy with their hearts and then justify it with their heads. And so just as you want to make them feel the pain of the problem, you also want them to enjoy the feeling that will come from solving it.


How do you do that?

More questions.

You could ask what it mean to them and their boss (or shareholders) if this problem was solved? This will take prospects outside of themselves. It’ll remind them that their challenges aren’t theirs alone.

Everyone works for someone and so when prospects solve their problems, it not only pleases them; it makes everyone else happy, too.

And even though you’ve been told what the organisation can’t do because of the problem, when you ask what it could do if it was solved, then that enables prospects to imagine their future.

You’ll recognise this as building the dream. The “dream” isn’t limited to people who want to see mountains in their picture window when they build a new house. It applies to people when they buy most things.

They imagine how they’ll look when they buy certain clothes or particular kit or drive a luxury car.

Then you want to remind them of the pain again. You could ask them what has prevented them from solving this problem in the past, and what they’ve tried. Learning what they’ve tried will save you the embarrassment of suggesting something that already hasn’t worked.

You can ask them what happened when they tried each of the things that they attempted. Maybe they had a management consultant in who couldn’t fix it, and even though you’re a consultant as well, they’ll still be interested to hear your ideas. You’ll get a lot of valuable feedback by asking why things didn’t work.

Of course, when you ask them to tell you about past failures, then they relive the pain of that experience. And that’s a good thing because of the stark contrast it will make against the feeling of solving it that they were basking in a moment ago.

And then you can ask how much longer they’re willing to put up with it. When you do that, you’re implying that it’s “make your mind up time.”


Status quo vs change.

Which is it?

You don’t even need to say that.

They feel it.


Why do challenging questions like this sell?

It’s because they prove that you’ve thought deeply about their needs. Even if you didn’t know exactly what they were beforehand, you’ve forced to relive the pain of having them. It’s a funny thing, but quite often people will have a high regard for you if you let them do all the talking. They’ll think that you’re a great person. And so by causing them to talk about their problem, they’ll feel that you understand it to the same extent that they do.

And when you ask questions like that, it also sets you apart from every other salesperson who hasn’t. That’s because of the depth of the conversation. You’ve obtained the facts that you needed, but have also shown empathy - a vital part of listening and advancing the sales process.


What challenging questions should you ask?

You’ll think of a lot of them if you take to heart the ones mentioned earlier, but there’s something else that you can do, too.

Ever hear an interviewer ask a famous person, “What do you get asked the most?” That’s a good question because it acknowledges that most people ask the same things over and over again.

So a question like that gets all of that out of the way at the beginning, and gives the interviewer scope to dig deep into that person’s activities.

You can do the same thing. You can ask yourself what questions your competitors usually ask, or what questions you would normally ask, and then think about how to improve them.

What do actors get asked the most? “How do you remember your lines?”

What do novelists get asked the most? “Where do you get your ideas?”

You could ask much better questions simply by putting yourself virtually into the shoes of the person with the problem.

With an actor, you could ask something that presupposes that the lines will have been learned. For instance, you could ask about tone of voice, accents, diction, etc. They would talk about the lines, but at a much deeper level. Hardly anyone ever asks about those things.

Or with a novelist, you could ask, which comes first: “The title or the story?” And then follow that up quickly with “Why?” for both.

“Why?” is an excellent question. That’s because it forces the other person to explain the rationale behind something.

Most people limit themselves to “What” or “How” questions. Those are far easier to answer.

“Why?” is much harder.


Why do you ask the questions that you do?


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