
Gary walks into his first sales job feeling confident he’s going to slay every deal.
He was the most popular guy in school and uni. He manipulated all the cheerleaders into being his girlfriends and all the other footballers into being his minions. He also always managed to get project deadline extensions from his teachers. Nobody else ever got deadline extensions.
But Gary is the smoothest of all smooth talkers.
The suavest of all manipulators.
He can sell ice to an Eskimo with his gift of the gab.
Well, that’s what Gary believes, anyway.
So as he attempts to close his first deal, he tells his prospect, “Well, if you cannot go higher than $750, then we can still work the deal but without XYZ component of the solution. I cannot include XYZ at this rate.”
Gary knows that the prospect really needs the said component. That’s one of the main reasons why they’re even considering the solution.
(You’re a smart sales professional – you already have a good guess about where this is going, don’t you?)
Gary struggles not to grin as he waits for the prospect to cave.
Imagine Gary’s surprise when the prospect says, “In that case, I’m going to shop around a little. That service component is very important to me. I’ll get back to you in case I decide to go with you.”
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That’s what happens when you try to manipulate or bully the prospect into closing a deal.
Why closing techniques need a re-look
Shouldn’t you try every sales technique that ever worked?
Why are we suggesting that some techniques don’t work anymore?
Aggressive, pushy, and devious closing techniques might have worked back when prospects had fewer choices and when researching products was more of a task for them. Salespeople might have been able to corner or manipulate prospects into a positive purchase decision when they lacked other options and could not verify the salesperson’s claims.
But today, Gary’s prospect could probably call five of Gary’s competitors within ten minutes to get quotes and could easily rubbish Gary’s claim about the service not being available at $750 with the desired component. He might not even need to call. He could even chat with their chatbots.
Here’s a few signs that your sales team needs new and improved closing techniques.

- Although you have a lot of leads at the top of your sales funnel, no deals seem to be closing
- Customers almost close and then disappear wordlessly, never responding to your reps ever again.
- You work with an experienced team that honed its skills in the 70s and 80s when Alec Baldwin’s famous film Glengarry Glen Ross was a hit. They’re big on his character’s ‘Always Be Closing’ mantra.
- Or maybe they’re a young lot who are inspired by Leonardo DiCaprio’s character in the Wolf on Wallstreet.
- Or they’re huge red pill fans.
- You notice in your call reviews that often a potential customer’s tone sharpens, or that their outlook changes, or that the warmth in their voice disappears after your sales reps try a particularly slick move that might have worked in the past.
- They’re using any of the sales closing techniques we’re about to talk about.
5 sales techniques to avoid
The punishment close
This is popularly known as the takeaway close. We could also refer to this one as the Gary close because it’s the one that our cheerleader’s favorite, Gary, from this blog’s introductory analogy, used.
How it works: In this close, you typically remove benefits that you had previously offered to the prospect when you reach a price negotiation or when the potential customer refuses to go above a certain price.

Why it does not work: Like what happened to Gary, the prospect might decide to go with one of your competitors or at least shop around.
If you go back and try to change what you said, it becomes apparent that you were lying the first time around when you said you cannot afford to reduce the price any further. Now they don’t trust you.
Even if the sale at hand goes through, the prospect might not trust you when you state your final price in future deal discussions. Even if you try to create a sense of urgency by telling them about an offer that is available for a limited time, they might not trust that the offer is truly limited.
Soften the blow: If you truly cannot reduce the price being offered any further and the prospect truly cannot increase their budget, you might try to be more upfront about the costs related to various benefits so that the prospect can choose which benefits they really need within their budget. Don’t hold them at ransom using a benefit that is driving the purchase in the first place. That’s like shooting yourself in the foot.
The never-a-good-time close
Hubspot calls this one the “cradle to grave” closing technique.
How it works: When the prospect indicates that now is not a good time for a purchase, saying something like, “budgets are tight this quarter” or “I haven’t the time to evaluate a new accounting software because I’m insanely busy with the financial year ending” you do not take no for an answer.

You tell them that there’s never a good time to buy and keep pushing.
Why it doesn’t work: You come across as inhuman, unempathetic, and like a know-it-all who is actually quite silly. Of course, there’s a bad time to buy. People need to have time to evaluate the benefits of a possible investment before they buy. They also need to have room on their priority list so as to allocate a budget to the purchase.
This close makes the prospect feel ignored and unheard. Yes, even though you’re breathing down their neck.
Guess who isn’t getting a meeting when budgets are better next quarter.
Patience is a virtue: Wish the prospect good luck with whatever makes now a bad time for a purchase. Ask them when you should call again. And then call again then. Be sure to ask how the event that was an obstacle to the purchase went.
The either/ or close
You might refer to this one as the “treating the prospect like a child” closing technique or the “alternative” closing technique.
How it works: The salesperson, after leading the prospect through the sales cycle, says, “So do you want the basic package or the premium package?”
There are only two choices provided. There is no third choice of not opting for either package.
Why it doesn’t work: Your prospect can see you playing games and trying to corner them. They’re well aware that they have a third choice. Phrasing it this way doesn’t take away their third choice. It only serves to make you come across as manipulative.

Now they’re second-guessing everything you said. They might not even know why they suddenly don’t trust you, but they don’t.
Upfront is never an affront: Call it our version of the popular ‘honesty is the best policy’, but it's the truth. Simply ask your prospect if they think they’re ready to buy, and when they say yes, suggest the options available.
The sharp angle close
Some sales professionals call this one the “end of story” closing technique because of how the salesperson tries to accelerate the prospect’s journey to the bottom of the sales funnel.
How it works: When the prospect asks a question, like “does your accounting software have a tax calculation component for our geography,” the salesperson responds by saying, “If it did, would you subscribe today?”
They don’t answer the question. They answer the question with a question.

Why it doesn’t work: Answering a question with a question is widely quoted as a sign that someone is not to be trusted.
Moreover, you are leading the prospect off track. The prospect is showing interest in your product and is probably open to having it deliver value to their business. But you interrupt that train of thought and focus simply on the sale. So you’ve brought the focus back to the transaction (when they were thinking about value), and you’ve effectively made them distrust you. Are you still surprised that they shut down?
To close, be open: Welcome questions from your prospect. They’re a sign of interest. Use your answers to highlight your product’s value and its edge over its peers.
The “sympathy” close
Call it what you like: The Oliver Twist close. The pity party close. The sad salesperson close. The “I need to feed my family” close. Some people call it the sales race close.
How it works: This type of closing technique uses emotional blackmail to get the prospect to sign up. The point is to use the personal relationship you have developed with the prospect and attempt to get them all worked up about your goals and problems.

To most sales reps, this already sounds wrong. Sales focuses on the prospect’s goals and challenges, not the sales rep’s goals and challenges. And yet, this technique is still in use.
Why it doesn’t work: No prospect wants to buy something to help your life. They buy things to help their lives. They can tell you’re blackmailing them, and they’ll probably start avoiding you.
Genuine value over crocodile tears: If you want to close that deal, focus your energy on showing your potential client how they’ll gain value from your product right off the bat, value that their business needs here and now. Yes, you’re doing it to win that holiday in Italy that the Salesperson of the Year gets, but your prospect does not need to know that.
So how do you close effectively?
We’ve got a whole blog on effective sales closing techniques, including the popular something for nothing close, the assumptive close, the hard close, and the puppy dog close. The idea is to come across as a consultant or partner. As trustworthy rather than slick.
Through the sales process, you want to shine a spotlight on the potential client’s business obstacles and position your product as the solution to them. Alternatively, you want to showcase your product as a means for them to accelerate achieving their business goals.
That way, when you reach the closing phase, you use a straightforward question close like, “Are you ready to subscribe/ buy/ sign up?”
Or “What can I do to help you/ convince you to close this deal this month?”
Or, “Is there something about our solution that you are still unconvinced about and that’s stopping you from closing the deal?’
Compare these honest, human-to-human questions to those we looked at earlier. Aren’t these closing questions more likely to result in a favorable purchase decision?
It's always a done deal with Wingman
An engaged prospect who is confident about your product’s value and believes it is the solution to their business obstacles will most likely be open to buying your product. For that to happen, you need to keep prospects engaged, talk to their pain points, and battle their objections. You also need to forge a bond of trust with them.

That’s where conversation intelligence can help. Wingman is a conversation intelligence tool that offers:
- Intelligent call recordings, summaries and transcripts that allow you to focus on being your friendliest self on call. You don’t sound distracted because you aren’t jotting notes about prospect needs while they are talking. And yet, when you’re making your close, you have important points on your screen, so you can remind the prospect of why they want your product and how it will help them.
- Pre-call customer profiles that jog your memory and allow you to pick up where you left off. For example, we talked about avoiding the “never a good time” close and calling the prospect when they estimate they will have the time and the budgets required. When you go back to make that follow-up call, you have a ready profile of your prospect and details of your last conversation.
- Game tapes, scorecards, and live, on-call battle cards that can be used for sales training. Game tapes are recordings of your top sales reps in action - sales pitches, closing techniques, objection handling... the works.
- Call success metrics to help sales managers better plan quotas and forecast revenue. Dashboards for an at-a-glance view into sales activity.
- Integrations with Slack and CRM, which reduce the admin load on the sales team, allowing the sales reps to focus more on selling.
Want to test-drive Wingman and get a hands-on experience of how it works? Request a free demo today.
