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24 Sales Closing Mistakes That’ll Stop a Deal in Its Tracks (According to Experts)

Ask any sales rep what the hardest part of their job is, and I’ll bet they’ll say “closing.” After all, signing new customers and upselling existing accounts is how a rep makes quota. If they’re not getting prospects to sign contracts, they’re not going to hit their number.

There are a some killer mistakes you need to avoid if you hope to be successful. Here are 24 of the most prevalent — and devastating — closing fumbles reps consistently run into.

1. Discounting the Importance of the Discovery Call

According to HubSpot Sales Director Dan Tyre, closing is a process that spans throughout the full sales process. By his account, “Most deals are competitive in 2021 — but most prospects start with the same group of competitors. Whoever nails the first part of the sales process tends to be the one who will finish or close it. The discovery call is the new close call, so if you don’t ask the right questions the deal will just stop.

“When you identify a good fit prospect, you want to be very specific on your expertise and experience. For instance, you might say something to the tune of, ‘We help professional services companies in Canada with at least 100 employees who are looking to grow 25% in 2021 and feel like they need to spend more time and effort on their digital efforts.’

“I like to continue these conversations with a discovery call where we can dig in and find the biggest issues that cause the most pain. Two great questions that I like to ask in this phase of the process are, ‘What do you love about your new business development efforts?’ and, ‘What do you want to improve?’

“I also like to address the ‘we have decided not to start’ objection — which is universal — right upfront. ‘When do you need the problem solved?’ ‘When do you need to see the cost reduction?’ ‘When do you need to get the customers by?’ All these questions create that mindset of moving to solve the problem sooner rather than later.”

2. Closing Only Once

As Dan stressed, you should consistently “close” throughout the sales process — for three main reasons. First, you’ll gradually secure greater and greater buy-in from your prospect. Second, you’ll filter out tire kickers. And finally, you’ll get key information, meetings, introductions, and more.

For example, on your first call, you might ask for the buyer’s cell phone number. Being able to call or text them directly — as opposed to going through their assistant or calling their work line — will make them much easier to contact.

At the end of the third meeting, you could ask them to connect you with procurement so you can start learning about their purchasing requirements. Not only will you have a head start over other vendors, but you’ll also seem more prepared and experienced.

3. Not Asking for What You Want

Clearly stating your ask might be common sense, but it’s hardly common practice.

There are two reasons reps don’t simply state what they want from a prospect. They might be afraid of rejection, so they soften their language to minimize the chances of hearing “no.”

On the other hand, it’s possible they don’t know what they want! Too often, reps go into a call or meeting with no real concept of what they’re hoping to get out of it. And if you don’t know what you want, how can you get it from the prospect?

Enter every interaction with a clear objective in mind, and don’t beat around the bush when asking for it. For example, “I’m calling to see if you have questions about the proposal,” doesn’t make it clear what you want the prospect to do. “Will you be signing and sending the proposal today?” does.

4. Using Statements Instead of Questions

Closes should always be phrased as questions, not statements. Why? Because questions require direct answers — statements don’t.

If a sales rep says to a prospect, “It would be great to meet on Monday afternoon,” that prospect can respond in a multitude of ways. But if the rep says, “Can you meet on Monday afternoon?” the prospect has only two possible replies at their disposal — “Yes, I can,” or “No, I can’t.

Sentences that start with “I’d like to” or “Maybe, we can” aren’t closes. Questions that start with “Are you,” “Can you,” or “Will you” are.

5. Not Getting a Personal Buy-In From a Prospect

Another point that HubSpot Sales Director Dan Tyre drilled home had to do with the value of giving your prospect a personal stake in your sales process. According to him, “The other mistake I see in the closing process is not getting prospects to buy in for personal gain.”

“I like to ask, ‘How can we make you look good in the process and when you start?’ and, ‘How can we make your boss and team look good?’ Those kinds of questions will ensure that the prospect is thinking about the benefits for them and their team for moving forward.”

6. Not Creating a Sense of Urgency

Purchasing decisions are driven by two things — need and timing. If a need is great but other priorities are more important, your deal will get pushed. If a need is great but the prospect doesn’t understand why they need to address it right now, your deal will also get pushed.

Identifying pain isn’t enough to close a deal. You have to create the right timing as well, and that means creating a sense of urgency. Explaining to your prospect not only why they should act but why they should also act now is the only way to close a deal.

7. Not Embracing Silence

Silence can be uncomfortable, but it’s golden when closing. Unfortunately, reps often rush to comment on their prospects’ responses immediately after they’ve been uttered.

Here’s what this sounds like:

Rep: “Can you meet this afternoon?”

Prospect: “No, I’m busy.”

Rep: “Not a problem — how’s tomorrow?”

However, if the rep simply falls silent after the prospect responds, the prospect often answers the rep’s follow-up question before it’s even spoken.

Here’s the above example, revised to use this approach:

Rep: “Can you meet this afternoon?”

Prospect: “No, I’m busy.”


Prospect: ” … But I can meet next Tuesday.”

Leaving some space can pay off in spades, so don’t get in your own way by jumping to fill the silence.

8. Not Knowing the Prospect’s Decision Criteria

Asking for the business is a way to signal to prospects that the end of the sales process has arrived. Of course, you also need to be aware of when it’s time to ask for it. Asking too soon makes the prospect feel rushed, but asking too late will make the deal last longer than it has to.

At the beginning of every sales process, make sure you find out what specific criteria the decision-maker needs to make a purchase. Do they need the vendor to follow a certain review or legal process? Do they need a specific set of features or a specific business case to be built? Find out these criteria and fulfill them methodically so a natural endpoint becomes obvious.

9. Not Understanding the Prospect’s Purchasing Process

Understanding the purchasing process is a similar, but slightly different requirement than the one above. Some companies require a legal review or formal procurement process to get a deal done. Others are required to evaluate a certain number of vendors. Still, others will have specific requirements for payment terms or types.

Know this process before formal negotiations start so that you won’t get through the entire closing sequence only to have to go through a weeks-long review process before the deal can be signed.

10. Closing Before Everyone Is at the Table

Negotiating with the wrong people is a waste of time. They won’t be able to tell you whether a decision can be made or what it will be. Bring in all necessary stakeholders and have them up to speed on your progress thus far before you start talking about pricing and terms.

11. Closing People Who Can’t Deliver

Why pose an ask to someone who can’t give you what you’re asking for? It’s not a good approach, and yet, I see this happen all the time.

A classic example is asking for a referral from someone who obviously cannot provide it. An entry-level engineer can introduce you to their coworkers and their direct manager. But the CEO? Probably not. Don’t ask a contact to commit to or give you something they can’t provide.

12. Getting Caught Up with NINA

HubSpot Senior Sales Manager Katherine Fischer recommends sales reps stay wary of getting involved with NINA. Who and what is NINA?

“NINA stands for No Influence No Authority. It is someone who talks a great game — they have a lot of experience over the years, telling salespeople exactly what they want to hear but are a total waste of time.

Your biggest mistake with a NINA is to try to close them for anything. You should not try to close for next steps, an introduction, nor anything else. Let’s say they agree to a next step. In that case, you’ll be wasting time building a relationship with someone who can’t progress the sale in any way.

That said, this doesn’t mean they are of no use. Nina is a great coach, you just need to recognize the limits of their contribution.

You can gather information from them to then later craft very personalized emails to key stakeholders. For example, you can ask NINA questions like, ‘‘What is talked about most frequently in the company meetings?’

13. Attempting to Close Someone Through a Third Party

I most often see this mistake crop up with senior-level decision-makers. Let’s say a rep wants to assemble all the relevant stakeholders they’d need for a deal to be approved, and they want to know who should be on the meeting list. If the rep can’t get through to the CEO, they might pose their ask to their assistant like so: “Who do you think your boss would recommend to be there?”

With this question, you’re asking the assistant to deliver what you want on behalf of their boss. Not a good idea. While it’s fine to pose your close to the assistant or a third party, make sure you’re closing the actual decision-maker directly. With this in mind, the above question becomes “Who do you recommend should be there?”

Close the person you’re talking to, not that person on behalf of someone else — the latter approach is a recipe for misunderstandings.

14. Using Underhanded Closing Tricks

Up to this point, you should have run a straightforward and honest sales process — so why stop now? Too many salespeople fall back on tricks and techniques designed to persuade their prospect into closing before they’re necessarily ready to.

The problem with those tricks is that they’re completely transparent, put unnecessary pressure on buyers, and don’t work that well. Keep your behavior above board throughout the sales process, unless you want to leave your buyer with a bad taste in their mouth at the eleventh hour.

15. Waiting Too Long To Address Questions and Objections

HubSpot Partner Channel Account Manager Jill Fratianne suggests reps stay on top of any issues and concerns prospects might raise. According to her, “The biggest mistake is waiting for the close to get every possible question or objection handled.”

She suggests that reps “ask all the ‘closing questions’ early on — especially when it comes to any legal processes or deal-breaking technical questions.”

16. Closing Too Early

Just as you wouldn’t pitch your product on the first call, you shouldn’t go for a final close when you’re only halfway through discovery. The sales cycle can and should be sped up if it’s possible to do so without cutting corners, but often you’ll need to follow each step and work on the buyer’s timeline to get a deal signed. Trying to force a sale over the finish line when you’ve only completed a few of these steps will prematurely end a deal you could have eventually won.

17. Not Understanding Their Bottom Line

Making a sale isn’t the end-all, be-all. The deal has to be mutually beneficial to both parties, and that means not compromising on price or payment terms to a point where you’re harming your company.

Be accommodating where you can, and help your buyer out if they’re genuinely willing to commit to a purchase — but don’t agree to terms that are so far from your company’s bottom line that you’d be better off walking away.

18. Stepping on the Close

On that note, don’t step on the close. A rep steps on their close when they immediately tack the word “or” or “and” onto the end of their closing question. Instead of asking the prospect, “Would you be able to meet tomorrow?” and letting the question hang, reps often hastily tack on an additional phrase, such as, “Or are you available next week?”

Keep in mind that words such as “and” and “or” add choices to a conversation, when closing is about eliminating choices and pushing the prospect toward a simple “yes” or “no” answer. By adding an additional clause, you increase the possibility you’ll get a muddled or half response.

19. Talking Too Much

At the negotiation table, silence is your best friend. Salespeople routinely talk themselves out of a deal: Their prospect is fully bought-in and ready to discuss specific terms, but the rep gets so excited that they keep going … and going … and going … They accidentally introduce doubt into the buyer’s mind.

Poof. That’s the sound of money disappearing.

If you tend to be a chatty closer, remember this — no one ever listened their way out of a deal. Every time you finish introducing a new term, responding to a question, offering a concession, or most importantly, stating your price, you should shut up. And when your prospect says, “Sounds great, I think we’re ready to move forward,” wrap up the conversation and end the meeting.

20. Not Asking for What You Need

HubSpot Sales Team Lead Lindsay Kopit suggests reps be frank and upfront with prospects. She says, “If you’ve built trust with your stakeholders, you should feel comfortable asking for what you need.

“It might not make a difference to your prospect to sign before the end of the month, quarter, or year, but it could cost you a promotion. Be honest about your targets and you’ll be surprised with how willing prospects are to work with you — provided you’ve built a strong relationship throughout the sales process.”

21. Not Understanding Internal Decision-Making

Kopit also stressed the importance of knowing how decisions are made from your prospect’s end. She says, “It’s easy to get carried away with a prospect who is excited about your product or service, but it’s important to remember to get buy-in from everyone involved in the decision-making process.

“Statements like ‘Have you made a similar purchase in the past? Walk me through that,’ can help uncover other stakeholders and avoid roadblocks at the end of the sales process. Is there a procurement process? Does the deal need sign-off from the board? Knowing this information ahead of time ensures you are on the same page as your prospect and timelines align.”

22. Being Overly Persistent When the Prospect Says “No”

If your prospect turns you down, the worst response is arguing with them. That sends a clear signal: You aren’t confident enough to accept their “no.” They’ll lose faith in you — not to mention your rapport will suffer.

So, what should you do? Just say “okay.” If another alternative makes sense, you can offer that one. For example, maybe they didn’t want to connect you with procurement because they think it’s too early, so you respond, “I understand. Is there someone else within the organization familiar with your buying criteria who may be able to give me similar insight?”

Showing you can calmly get a “no” without becoming irritated, pushy, or insecure will raise your status in the buyer’s eyes and increase the odds next time you’ll get a “yes.”

23. Trying to Make Closing Easy for the Prospect

Reps often ascribe to the thinking that closing needs to be easy for the prospect, but that’s wrong. By definition, closing requires the salesperson to put the prospect in a mild state of discomfort.

If buyers don’t feel a slight amount of pressure, they’re not going to make a choice. And “no decisions” are always worse than closed-won or even closed-lost. Don’t be afraid to turn up the heat a few notches to get an answer.

Closing is tough, but avoiding these missteps and sticking to a confident, concise, and “always-be-closing” mindset will set you up for success.

24. Closing When You’re Not in a Closing Position

HubSpot Principal Account Manager Leticia Henry framed this point with a baseball analogy. She said, “If you think of the sales process as a baseball diamond, each base represents a different step in the sales process.

“Successful salespeople sell consistently because they follow a consistent, repeatable sales process. They have a clear understanding of both the purpose of each step and the outcome of that step.

“Like baseball players, sales reps who take the time to pass through each base know that while the process might be longer than hitting a home run, they are more likely to close the deal — or make it to home — more consistently.

“Sales reps often try to close a deal when they’re not a position to do so — that’s to say they’re on first or second base, but are trying to reach home base in one swift run. That may work some of the time, but it will not help you close reliably.

“You need to get in position to close the deal — to get to third base consistently. Being on third base means that you can answer ‘yes’ to the following questions: ‘Are you talking to the decision-makers?’ ‘Does this customer recognize that they have a problem?’ ‘How much does the customer want to fix this problem?’ ‘Does the customer want my help fixing it?’ ‘How much does the customer believe that my solution can help solve the problem?’

“If the answer is ‘yes’ across the board, you have successfully put yourself in a position to close. If the answer is ‘no,’ take a moment to consider a few points. Reps in this position need to ask, ‘Where am I in my sales process, and what will it take for me to hit my next step?’

“Home runs are marvelous, but you can’t bank on them to consistently make it home. I have about a 60% close rate. Among the reasons behind my success in closing is because I follow my process every time. I do not go for the close until I’ve covered all of my bases, every time. I don’t close until I am in a position to close, every time. You need to put yourself in a position to close if you want to close consistently.”

Closing is tough, but by avoiding these missteps and sticking to a confident, concise, and “always-be-closing” mindset will set you up for success.

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