How To Encourage Prospects To Open Up & Engage

April 27, 2016 Geoffrey Walters

‘Help me help you! Help me… help you!’

When faced with a prospect who just will not open up, many salespeople feel like repeating Jerry Maguire’s famous words. It’s not that the prospect objects, exactly - it’s more that they just won’t tell you what they need.

Yelling at them probably only worked for Tom Cruise because it was a movie, though. In the real world, sadly, that’s not a tactic that’s likely to work. So let’s have a look at some more tactful ways of bringing a prospect out of their shell so that you can get the information needed in order to make a sale.

Why Are Some Prospects Reluctant To Talk?

Reluctant Shy

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It’s frustrating when we can’t get people to talk. In social situations, people who are naturally reticent often get branded ‘difficult’ or ‘rude.’ And when you’re on the phone with someone who ‘ums‘ and ‘ahs‘ around the point but won’t tell you what they want, it can make you feel the same way. But thinking of ‘closed-off’ prospects like that is counterproductive for two reasons: Firstly, it will give you a bad attitude towards them, and that will come across in your tone and make a sale even more unlikely; and secondly, it fundamentally misunderstands why a prospect might not want to open up.

Instead of getting annoyed or dismissing the prospect, try to see things from their point of view. They might be very loyal to their company, and feel that they’re standing by their firm by keeping quiet:  ‘loose lips sink ships.’ That’s actually an admirable stance that shows the prospect’s integrity. If you can get such a prospect to open up and persuade them to buy from you, you are likely to have an honest, long-lasting relationship.

Another reason for a prospect’s reticence might be that they’ve previously been sold a pup and want to avoid repeating their mistake. ‘Tight-lipped prospects aren’t trying to be difficult,’ says Steli Efti, CEO of ‘They’re trying to be safe.’ For prospects like these, you need to find a way of reassuring them that their experience will be different if they buy from you.

Prospects can also be reluctant to engage with you because they don’t feel that they have a problem your product can solve—even if they do. ‘The greatest barrier to someone achieving their potential is their denial of it,’ wrote the author Simon Travaglia, and that is why this type of prospect is the hardest to persuade to open up.

In his book Slow Down, Sell Faster, Kevin Davis describes this type of “in-denial prospect”:

‘In-denial prospects are people who are unwilling to talk about either their problems or their opportunities for improvement. They believe their performance is optimal, but they are mistaken. These are the most difficult prospects to sell to because they are unwilling to admit a need.’

In-denial prospects are a breeze compared to angry prospects, however. Getting angry prospects to talk isn’t the problem—the angriest ones might hit you with a stream of invective—but getting them to take you and your product seriously can be nearly impossible.

Again, the key is to understand the reasons for their behavior. Why are they angry? ‘Maybe they’ve been prospected by your company before,’ writes SalesLoft content marketing specialist Leah Bell in Forbes.

‘Maybe they’ve had a bad experience with a similar product.’ After all, most companies that implement a SaaS solution try several for each need before they hit on something that fits. You might be catching their disappointment with their previous tool - or, conceivably, their frustration with the one they’re currently using! ‘Maybe,’ Bell continues, ‘they’re just plain having a bad day.’

Trust Issues

Trust Issues

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The in-denial prospects excepted, the problem you face as a salesperson with a reticent prospect boils down to this: the prospect does not know who you are. That’s why they’re not 100% cool with talking to you. ‘You’re an unknown quantity,’ writes Ryan Caligiuri in The Globe and Mail. ‘One of the main reasons prospects don’t want to talk to you is because they don’t trust you.’

Whether they’ve had poor previous experiences, want to protect the company or simply are cautious by nature, the prospect needs a reason to believe that you are not going to let them down. Any tactics that you use to encourage such a prospect to open up should then be centered on building trust. Let’s have a look at a few approaches that can help you do just that.

Ask Different Questions


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Try to empathize with your prospect. If you were a loyal employee who was reluctant to open the book on the company’s secrets, what questions would you absolutely refuse to answer from a salesperson? And conversely, what kind of thing would you be willing to talk about?

Try framing your questions in a more positive way. Instead of asking the prospect to pinpoint what’s going wrong, encourage them to highlight areas that could be improved. A loyal employee will often feel more comfortable if they feel they are talking positively about how their company could be improved rather than pointing fingers at where things are going wrong.

‘If you sense that your prospect is reluctant to open up and talk about their company’s problems, change the track of your questions,’ says Davis. ‘Don’t focus your questions around problems (don’t ask “what’s not working in your business?”). Instead, ask about potential opportunities for improvement. Ask, “Where do you think your organization can improve? As well as they are doing now, what do you feel they can do better?”’

While offering hope that such prospects can be brought out of their shell, Davis also makes a key point about time management and pragmatism: ‘If they won’t open up then, either, it’s time to move on to another sales opportunity.’

More of that later.

Hit Them With Some Straight Talk

straight talk

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Approaching the situation with sensitivity works for some reticent prospects. For others, it’s better to get straight to the heart of the issue. Make direct reference to the prospect’s cautious behavior. Say that you know why they might be clamming up and why it isn’t necessary with a scrupulous, respected company like yours.

Steli Efti suggests saying something like this:

‘I bet you’ve had a bad experience with a salesperson before. You might think I’m here to take advantage of you, but I’m not… I want you to be successful, but I need you to be open with me. Help me help you and I promise we’ll find you a great solution.’

This type of approach has two benefits. Firstly, it can alert the prospect to the fact that they are behaving reticently. The chances are, they might not even know that they had been acting cautiously—how often do we rely on the advice of friends, family and colleagues to make us aware that we are behaving in a certain way? Secondly, it will cast you as a straight talker, someone who is honest and forthright and willing to address issues head-on. This will help foster trust.

In his correspondence example, Efti suggests even going as far as telling the customer you will walk away from a deal: ‘If I’m not 100% certain we’re a perfect match, I’ll tell you. In fact, I’ll even refuse to sell to you.’ Again, this shows a commitment to quality over chasing sales and will promote trust. Efti says this type of correspondence should be conveyed with ‘friendly strength, not frustration or anger.’ Put yourself in the prospect’s shoes before you contact them and empathize with them rather than becoming annoyed with their cautious behavior.

If They’re Angry, Don’t Take It Personally

It’s hard to be confronted by someone who is angry, harder still when you’re not responsible for that anger. In this kind of situation, when we feel an injustice, it’s easy to take things personally and let emotions drive the exchange. Try to avoid getting too involved and remember the central issue: trust.

‘You haven’t even introduced [the prospect] to your company or product, much less the solution you offer, and they’re objecting already…because they don’t trust you,’ writes Leah Bell.

Anger is often driven by mistrust: The idea that you’ve relied upon someone and they’ve let you down. Gently take control of the call by reminding them that it wasn’t you that let them down and that, in fact, you can offer them a far more satisfying experience than the one that has got them all riled up.

‘They don’t know you, and they don’t believe you are worth their time,’ writes Bell. ‘But don’t take this objection personally—you can counteract it by acknowledging the fact that this is a first-time conversation in your introduction… Establish that you are trying to earn the right to talk to them and take that objection off the table.’

What If Your Approach Has Angered The Prospect?

angry customer

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Sometimes the straight-talking approach will anger the customer. They will see your request for transparency and honesty from them as unnecessary prying. Reminding them that they got burned in the past will irritate them. ‘There will always be a couple of prospects who say, “This is the way we buy. If that doesn’t work for you, we’re through here,”’ writes Steli Efti.

If you’re an ethical salesperson, that creates a dilemma: How can I sell to this client in good conscience without knowing the ins and outs of their situation? Efti’s salespeople at are instructed to tell the client they are unable to make a deal in this situation because they don’t know enough about the client’s situation.

This approach will elicit one of two responses. Either the prospect will say, ‘Thanks, but no thanks,’ and walk away from the deal, or they’ll realize they were interested after all. If they don’t step up and engage, then it’s goodbye - but better that than running in circles, chasing a deal that’s realistically never going to happen. If they do engage, though, you’re in a way stronger position to close the deal.

Be Ready To Walk Away

walk away

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Sales guru John Barrows has written about the power shift that walking away can cause. Although he is writing here about using deal abandonment as a closing method, the psychology is the same as when you are simply trying to qualify a prospect.

‘For the most part, the buyer usually thinks they are the ones in power throughout the process and they typically act that way (some more offensively than others),’ writes Barrows. ‘When you pull the walk-away close, you change that dynamic.’

Barrows suggests having a defined walk-away line across the business, a point beyond which you will refuse to go as a salesperson. One place he suggests drawing the line is when you’re looking for ‘a level of equality that simply needs to be there in the relationship.’ A prospect that simply will not divulge key information holds too much power, meaning the relationship with the salesperson is too imbalanced and needs to be either abandoned or redressed.

Having such a clear line not only simplifies the decision-making process for the salesperson, who now has a defined point at which they will abandon a deal and no longer has to rely on gut feeling, but it can help the salesperson do what we discussed earlier: take emotion out of the equation.

‘[H]aving a walk-away line allows us to limit the emotions involved in many negotiations,’ writes Barrows. This allows us to face angry customers with more serenity than we might previously have mustered, making us more likely to be able to calm them down and get them talking about their business’s problems—and what solutions you might have for them.

Some People You Just Can’t Reach

can't be reached

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Of course, there are some people who simply won’t admit their business has a problem: Davis’ in-denial prospects. He gives blunt advice on how to deal with them: ‘Candidly, these are prospects you should get rid of,’ he writes. ‘Don’t waste your precious time on them, as you will get nowhere.’

Remember, you can only help them if they agree to help you.

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About the Author

Geoffrey Walters

A serial entrepreneur and digital nomad, Geoffrey has been running his own marketing consultancy for the past year.

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