How to Handle 5 Common Tricky Sales Situations

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Aja Frost
Aja Frost



In a perfect world, every interaction with your prospects would unfold smoothly. But occasionally, tricky situations arise. Although you can’t always control whether these situations occur, you can control your response.


Not only will reacting well to an awkward or difficult moment make your prospect respect you more, it’ll also teach you to remain graceful under pressure. Ultimately, you’ll keep the deal on track while boosting your people skills. These five tricky situations may have an upside after all.

1) You Disagree With Your Prospect

Challenging your prospect can feel like stepping on their toes. If you suspect they won’t react well to a direct approach, dig into the reasoning behind their opinion. Once you understand why they think what they do, you can tactfully present a different view.

Here’s some sample dialogue illustrating this strategy:

Prospect: “I think over-the-top content’s (OTT) rise is overhyped. The cable industry will be fine.”

Rep: “Interesting. Would you mind explaining?”

Prospect: “I read a report from Leichtman Research Group saying 82% of TV households have a paid TV subscription.”

Rep: “How does that percentage compare to a few years ago?”

Prospect: “It’s dropped several percentage points. But eight in 10 households is still a substantial amount.”

Rep: “Can I offer a different view?”

Prospect: “Sure.”

Rep: “A growing number of people are complementing their cable packages with OTT. According to PwC’s 2016 media forecast, 78% of people subscribe to at least one OTT service. I suggest offering smaller, less expensive, flexible cable bundles to appeal to these consumers.”

2) You Made a Mistake

Making mistakes is inevitable. Maybe you gave the buyer wrong information, broke a commitment, or forgot about an important meeting.

If you apologize the right way, your blunder won’t cost you the deal. On the contrary, it might strengthen your relationship with your prospect because you’ve proven you’re human and willing to own up to your mistakes.

Demonstrating humility and honesty is crucial. You should also offer a suggestion or solution.

For example, you could say the following:

“I messed up. When we met last week, I told you I could waive your shipping fees for the rest of the calendar year if you signed the agreement this month. I spoke too soon: My manager won’t sign off on that. I apologize. Can I make it up to you by introducing you to my good friend Richard Thomson? He’s a Graves consultant, and he’d have some great insights into the problems you’re experiencing with your overseas manufacturers.”

3) You’re Dealing With a Hostile Prospect

When you’re working with several stakeholders at a single company, one or more might dislike or distrust you. Don’t simply ignore that person and focus your energy on the others. You’ll have a better chance of pushing the deal forward if everyone involved in the decision supports you (or at the least, doesn’t actively want to block you).

One of the best ways to win over a hostile prospect is to identify what he wants, then help him get it. If you have an internal champion, ask her how the detractor’s job performance is measured, what his personal and professional goals are, and his criteria for this product decision.

Come up with one or two ways you can aid him in achieving his objectives or boosting his reputation. For instance, perhaps he’s a PR manager whose success is primarily tracked by earned media, publicity received from promotional efforts. You might offer to connect him with a journalist so he can send relevant press releases her way. Once you’ve done someone a favor, they usually go from hostile to eager to help.

4) Your Prospect Blows You Off

Many salespeople routinely deal with no-show prospects. Letting buyers break their commitments with no consequence can make you seem less important or worthy of respect -- which unsurprisingly works against you. On the other hand, chastising your prospects for missing your scheduled call or meeting may harm your relationship and cause them to resent you.

The first time a buyer flakes on you, don’t jump to conclusions. They might have a valid reason for not showing up. Send them an email explaining what happened on your end (i.e., “I called your cell at 8 a.m. and didn’t reach you”), then reiterate what you were planning to cover. End by proposing a rescheduled call at another date and time.

If they flake again, you should be more skeptical of their motives. It’s a waste of both your time and theirs to continue the sales conversation if they’re not truly interested in or ready to buy.

To figure out whether they’re ultra-busy or not serious about buying, send them an email along these lines:

Close Your File?

Dear [prospect name],

I called you today at [time] to discuss these points:

  • [Topic #1]
  • [Topic #2]
  • [Topic #3]

Is solving [challenge] still one of your priorities? Let me know before we put another meeting on the calendar. If it’s not a priority, I’ll close your file.

[Your name]


This template is direct and honest, but it doesn’t attempt to guilt the prospect. Staying neutral is key: Guilt-tripping may get people on the phone, but it won’t convince them to pull the trigger. You don’t want to invest resources into a buyer who’s talking to you out of obligation.

5) Something Awkward Happens

Awkward moments are inevitable. You forget your prospect’s name, something not strictly professional comes up on your computer while you’re sharing your screen, you make a joke that doesn’t go over well -- the list of potential cringe-worthy situations goes on and on.

But all is not lost. Your prospect will base their reaction on yours: If you’re flustered and embarrassed, they’ll perceive the snafu as a big deal, while if you’re calm and professional, they’ll probably move on quickly.

With that in mind, briefly apologize and then steer the conversation back to your planned agenda.

Here’s some sample dialogue:

Rep: “I’m sorry that came up on my screen. It won’t happen again.”

Prospect: “That’s okay, things happen.”

Rep: “I think you were telling me about your sales compensation plan. What’s the rationale for your current model?”

When you’re working with other people all day, every day, awkward moments and tricky situations are bound to happen. React the right way, and you’ll preserve your relationships with buyers.

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