8 Keys to Closing Tough Prospects, According to Sales Insights Lab's Founder

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Marc Wayshak
Marc Wayshak


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two salespeople in the process of closing tough customers

In an ideal world, every prospect would love you from the moment they first shake your hand. They‘d listen to your pitch intently, nod along with a big smile, raise no objections, and sign on the dotted line without pushback. Unfortunately, we don’t live in that world, and closing is never that easy.

In some cases, it can feel borderline impossible, especially if you're dealing with particularly tough prospects who make a point of making everything harder than it needs to be. Some potential clients try to push you around or waffle indefinitely over next steps — making deals drag on for weeks on end and ultimately go nowhere.

While you can‘t control prospects’ attitudes, you can control your responses — taking productive steps to increase your chances of closing, even when you‘re dealing with the worst prospects imaginable. To help you out, I’ve put together this list of eight key steps you can take to handle the potential customers that make you want to pull your hair out. Let's take a look.

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1. Show that you’re unfazed.

Difficult prospects are like sharks — if they sense blood in the water, they‘re going to go on the offensive. That means you can’t appear scared or nervous. If you do, those tough prospects will be even more likely to push you around.

Remain composed at every turn. Resist the urge to speed up a sales meeting or alter your approach when a prospect is being rude, aloof, curt with you, or just flat-out disagreeable. Being visibly impacted by a prospect's bad attitude is one of the easiest ways to lose your footing in a sales conversation.

Instead, show you're unfazed by sticking to your game plan — even if they pressure you to hurry things along.

2. Be unemotional and firm.

This point is kind of an extension of the previous one. It‘s natural to feel frustrated when a prospect is giving you a hard time, but frustration will only waste your opportunity — especially when you’re wearing it on your sleeve.

A prospect could be a bully, but they might still need what you‘re selling — so it’s in both of your best interests for you to avoid getting visibly upset and testy with them. Sales isn‘t about being best buddies with every prospect you engage with, so don’t take anything personally, and commit to standing your ground.

Keep your emotions in check and stay on track with your regular approach to closing sales.

3. Get prospects talking about their challenges.

Difficult prospects might have a million different things on their minds. If that‘s the case, they probably don’t want to listen to you. Instead of forcing them to listen to what you want to say, flip the script — and get them talking about themselves and their pain points.

With this approach, you’ll tap into their emotional side and break through the animosity. Getting prospects who are reluctant to commit to talking about their key challenges can also help you gauge how much of a priority solving their problem actually is.

4. Understand prospects’ top objectives.

In a similar vein as the previous point, you want to get difficult prospects talking about their immediate objectives. Ask them what their most pressing, short-term goals are with questions like, “What are your top priorities in the next six, 12, or 18 months?

That will give you the necessary perspective to align your solution with their objectives — establishing fit and creating a sense of urgency with even the most noncommittal prospects.

5. Get real commitment.

Before you get to your proposal, you need to find out how serious a prospect is about solving the challenges and reaching the objectives they've spoken to you about — and sometimes, the best way to get there is by putting them on the spot.

But you don't want to ask about their commitment to buying your product or service. Keep things centered on them, and try asking something like, “Are you committed to doing something about this right now?”

By holding your prospects’ feet to the fire a bit, you’ll be able to gauge whether or not they’re ready to commit to what you have to offer.

6. Maintain conversational control.

Difficult prospects often wind up hijacking sales conversations — they pursue irrelevant tangents, steer subjects in different directions, speak over you, or take any other actions to derail the conversation until it's strictly on their terms.

As a salesperson, you always need to maintain control over the conversation — so if you notice things are getting out of hand, don't hesitate to politely interrupt with something to the effect of, "Excuse me, I‘d be happy to speak to this point more after the presentation, but I’d like to respect everyone's time by keeping to our agenda and staying on track."

This should allow you to wrangle the conversation back toward you and your prospect's shared goals.

7. Never try to prove your dominance.

"Did you know ...,“ ”Actually,“ and ”No offense" are all statements used to prove dominance — and in the context of a sales conversation, they‘re always missteps. They’re cheap power moves that won't serve you well when dealing with difficult prospects.

You want to position your authority when dealing with tough customers, but you need to be mindful of the line between “positioning” and “posturing.”

The former is about establishing yourself as a valuable, consultative resource for your prospects. The latter is about making yourself feel better after getting pushed around — and going there is always tempting when you feel you're being undermined.

But like I touched on with the first point on this list, you need to maintain composure in these interactions — project authority by remaining calm, sharing information objectively, and asking for your prospect's perspective.

For example, instead of saying, "Did you know industry experts predict widget production will triple in the next four years?“ try, ”I've heard widget production is expected to triple in the next four years. Will this affect your business at all?"

In the first example, you‘re trying to one-up your prospect with industry intel they don’t know. In the second example, you've presented them with a fact and asked for them to weigh in.

8. Remember, it's not personal.

Tough customers are just part of the game of sales. They‘ll never go away, but it’s important not to take their behavior too seriously.

Always be respectful in meetings, but if things get out of hand, leave it at the office. It's not a reflection on you and is likely a sign of personal struggles the prospect is facing. Go home, have dinner, chat with a friend, and unwind so you can come back tomorrow fully charged.

Tough customers are never fun — but they can still be profitable. With a game plan in place, you’ll be far less likely to fold under pressure or take difficult selling situations personally.

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