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5 Difficult Questions You Should Be Asking Your Prospects


When I ask my sales manager clients « what’s the biggest issue you struggle with in your sales teams ? », the answer is mostly different from what you’d expect. Once we dig beneath the surface, as it turns out, many of their sellers are not suffering from not enough opportunities, but from having too many.

Sound counterintuitive ? Luxury problem ?

Think again. According to IT Marketing World, « Up to 60% of deals in sales pipelines are currently not being lost to the competition, but are being lost to the status quo – the do nothing buyer.”

Our own research at RAIN Group puts the number slightly lower – around 25%. Still, depending on who you choose to believe, anywhere from a third to two thirds of all deals never materalise.

Now, we might ask ourselves the question : why exactly is that ? Valid question, but impossible to answer. The reasons why these deals don’t move forward are myriad, from lost or cancelled budgets to increasingly risk-averse, paralysed buyers.

So, rather than try to answer the unanswerable, let’s focus on another, perhaps more important question : how can we avoid to waste our valuable time, energy, resources and focus on deals that will end up going nowhere ?

The answer ? Questions.

Asking better questions, to be precise. Because unless sellers do their due diligence on buyers, they’ll (continue to) end up wasting between a third to two thirds of their time chasing deals that will end up going nowhere.

To my mind, there are 5 difficult questions you should be asking your prospects. All of them. No exceptions.

Warning : these questions are not meant to be asked literally, as phrased. They are here to serve as a guideline for uncovering five crucial pieces of information that you should uncover for every single deal.

1. Why not just keep on doing nothing ? »

As a seller in the early stages of the deal, your first order of business should not be to win the deal. It should be to find a valid reason to kick the deal out of your pipeline.

Because unless you enjoy spending time speaking with folks who have no intention of buying from you (but are happy to have you provide free consulting, generate ideas for them and « do a proposal »), you should thread very, very cautiously in the early stages indeed.

I’m not saying that every buyer is suspect, and I’m certainly not saying you shouldn’t take a hard, long look at everything that enters your pipeline.

I’m simply saying this. The first step in the sales process should be: attempt to disqualify.

Now, please don’t take this question literally, and go round asking well-meaning buyers why they shouldn’t just keep on « doing nothing ». Phrase it differently. One of my personal favourites is. « Why have you chosen to act, and why now ? ». It’s the same question, but asked in reverse. Unless there’s a clear, solid and immediate answer, that’s an orange light right there.


2. How bad do you really want this ? »

Around three in four deals fall under the category « strategic », meaning buyers buy primarily because they are seeking some kind of short- or long-term advantage. In other words, they’re not buying because they have to buy, but they buy because they’re investing in a better future.

Which poses a problem.

Because unless we have to buy, there are varying degrees to how much we really want to buy. Some things, we want bad. Others, maybe a little.

You may think that your latest and greatest remote monitoring SaaS app, your outperform-the-market-since-2010 investment fund or your high-end legal services are an absolute no-brainer, but never make the mistake of assuming your buyer feels the same.

In addition to clearly and unequivocally understanding why your buyer feels they must act, your job is to find out how strongly they want to act.


3. What’s your worst nightmare ? »

People are motivated by two powerful, human drivers : pleasure and pain. (I’m guessing you already knew that one).

What’s not so well known is that these two are not opposites, but exist along the same dimension, and influence each other. There are two powerful dynamics at stake here.

First, if the (perceived) risk is too big, buyers won’t act.

The problem is, they won’t tell you. Instead, they’ll come up with all sorts of rational-sounding reasons why they choose not to move forward. « Our strategy has changed » . « We’re pushing this into next quarter ». « My boss won’t sign off on it right now, but call me back in a month».

Second, if the (perceived) risk is too small, buyers also won’t act.

Don’t believe me ? Let me ask you this. If I had a way to make 100K overnight, while you were sleeping, with absolutely zero risk, would you buy from me ?

Unless you’re really gullible (and most buyers aren’t), chances are you’ll think to yourself « too good to be true » and move on. And again, you won’t tell me, or at least not directly.

When it comes to risk, as a seller, it’s your job to bring it up – proactively and early on.

This is the only way you’re going to get a clear view on how your buyers views the risks, and how that will influence their behaviour. (Incidentally, it also has the benefit of building trust and position you as an expert sales pro).

4. What should I know that I don’t right now ? »

At first, this one sounds odd. After all, this is a very broad question.

And that’s precisely the point. By asking a question this broad, you’re very subtly nudging your buyer to think of new pieces of information they can share with you. What comes out is often surprising. They’ll give you names of the 4 other firms they’re speaking with. Talk about how their boss is completely against the initiative they’re launching. Speak about how desperate they are to get their problem solved, and how they’re really out of options.

Point is : this question allows you to uncover all of those. It’s similar to asking, « Is there anything we haven’t covered ? » at the end of a sales call. Very often, surprising and unexpected things will come up.

5. How much are you willing to invest ? »

Where this one doesn’t always get a straight answer, it’s still worthwhile asking. In fact, I’ve found there is a direct correlation between how tight-fisted a prospect is with information about financials, and how likely they are to have the money to buy whatever you’re selling.

Read that again : if your prospect is hesitant to give you a number, range or ballpark, it’s often because they subtly know (or believe) they don’t have enough. And they’re hoping for you to unexpectedly come in within their budget. To string you along until you’ve given them a proposal.

In my own experience, all the large, rewarding and fun deals I’ve sold have been to folks who were open about their budget. That doesn’t necessarily mean they’ll give you a number. Sometimes, they’ll give you a range. A cap. A number at which procurement comes in. Sometimes, you will volunteer a number, and they’ll tell you there’s room on top of that.

But beware the seller who advances all the way to the proposal stage without having at least an inkling that their buyer is ready, willing and able to pay for their services.

So there you go. 5 difficult questions to ask your prospects. Five pieces of information you’ll need to uncover at the very start of the buying cycle.

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