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Sales - 7 min READ

How to Ask for the Sale More Confidently

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Author photo: Marina Fishman

Marina Fishman

Director of Sales

You want to set a good example for your sales team, to show them how not to let primed leads slip through their fingers.

Which means you need to be able to demonstrate how to ask for the sale, and to do it with confidence.

Now, there’s a big difference between fearing that a prospect might say no but asking anyway, and having so little confidence that you avoid asking the question altogether.

Bottom line: if you don't ask for the sale and rely on your prospect to step forward and say “I’m ready,” you’re more likely to lose the deal than if you were to take the direct approach.

Also, keep in mind that you’ve already done the hard part and laid the groundwork. If you listened to the prospect, related to their pain, and handled their objections, how likely is it that they’ll say, “No?” (Plus, a “no” doesn’t mean the deal is dead. More on that later.)

So, what really is there to fear?

It’s just going to take some practice—as well as an understanding that “no” isn’t always a bad thing.

Here are the six steps (you'll notice that preparation is key to many of these) to asking for the sale confidently:

  1. Prep the big question.
  2. Make sure you've got a good fit.
  3. Plan it for the right time.
  4. Do it in the right place.
  5. Choose your words wisely.
  6. Be prepared for when “yes” still isn't a guarantee.

How to ask for the sale and get more committed clients 

Commitment can be a scary thing for prospects. Of course, they wouldn’t have engaged with you or your sales team in the first place if they didn’t need what you were selling.

But the idea of settling down with one provider can be daunting, especially if they’re looking around, wondering if there’s someone else who can offer a stronger solution or a better deal.

That’s why there can’t be any fear coming from your side. If you’re nervous about asking for the sale, it'll only feed their apprehension about getting into business with you.

In order to be confident about asking for the sale, it helps to follow a specific game plan every time. Here’s what it should look like:

Step 1: Prepare for the big question.

In order to move confidently forward, you should make sure that you’re prepared. In other words, have you:

If you’re unsure, refer to your CRM to gather your thoughts.

For example, my team uses Copper to capture all of our past conversations along with notes we’ve made over the course of the relationship:

Use this as a reference in preparing your pitch.

Ultimately, your goal here is to step up to the plate and ask:

“Are you ready to move forward?”

You don’t want this to be a surprise for your prospect. They should expect that you’re going to pop the question, which means doing the work upfront to make it clear this is where the conversation is headed.

Step 2: Make sure it fits perfectly.

When you do get that “yes” from your lead, you should be prepared to present them with a proposal and contract.

But not any old proposal will do. It should fit them perfectly, which means being a good listener throughout the course of your relationship.

My team has a checklist for deals that every Account Executive needs to know. It consists of seven items:

  1. Are we the vendor of choice?
  2. Do we have access to "Power?" (Essentially, a decision-maker)
  3. What's the compelling event that is key to getting this deal done?
  4. What's the sign-off process?
  5. Is the budget there?
  6. What red flags should we be aware of?
  7. What's the plan for onboarding?

Again, your CRM will come into play as it has records of everything—every call made, every conversation you or anyone else had with them, every promising step made towards the sale.

You’ll then use all of this data to write the perfect signature-grabbing proposal ahead of time.

That way, when they say “yes” to your offer, there’s no need to delay with a lengthy engagement. You can quickly seal the deal and close the sale since you’ve accounted for everything they need and want in the proposal and contract.

Step 3: Plan it for the right time.

One of the things that might have you nervous about whether or not your prospect is going to say “yes” is the timing aspect.

For starters, is it too early to even bring up the question? And, if you jump the gun, would that ruin your chances for good?

Honestly, it probably won’t get you an immediate “yes,” but it also won’t hurt the sale. What you should be worried about is coming in too late with the question.

The more time you give a prospect to sit and consider what you’ve been talking to them about, the more time you give them to look at other options.

So, what you need to do is find your sweet spot.

Look at the historical data from your sales pipeline. For example, this is the Pipeline Summary report from Copper that we use:

You can see in this example that the average time it took the sales team to qualify a prospect is 21 days, while it took 22 days for them to send a contract to new clients.

Knowing this, you could then guess that somewhere around Day 40 is a good time to throw the question out there.

Another timing-related matter is the actual day and time it takes place.

Is the prospect leaving for a two-week vacation on Monday and you know they’re stressed about leaving?

Even though it might seem like a good idea to catch them before they leave for two weeks, it might not be smart to ask for a sale when they have more pressing matters on their mind.

Are their kids off from school this week, leaving their coworker to sub in for them?

Then, there’s no sense asking for the sale. Don’t waste the effort if you’re only going to have to work up the courage to do it again when your prospect is back in the office.

Do calls made after 10 a.m. tend to feel more enthusiastic since they’ve just finished their two daily cups of coffee?

Bingo! It’s details like these you need to make a mental (and digital) note of, so you can use them to reach your prospects at just the right time.

Image for post 🚀 your sales.

🚀 your sales.

Learn how to manage your sales pipeline and close sales efficiently with this handbook.

Step 4: Do it in the right place.

Time isn’t the only thing that’s going to help or hinder your ability to ask for a sale and close the deal. Think about place, too.

For instance, asking for a sale over email might not be a good idea if all of your conversations have been over the phone or in person. Switching contact channels at such a critical point in your relationship will only give the prospect an easy way to dodge the question.

When you finally do get the courage to call them up to see if they saw your message, they’ll probably respond with:

“Hey, sorry. Yeah… I think I did see something about that.”

An email is too non-committal and undermines the seriousness of what you’re asking. Plus, an email is just begging to prolong the “yes.” Of course, they’re not going to jump at the sale over email.

They have fears and hesitations about this. It’s natural. But that’s why you’ve been there all along, fostering a trusting relationship and helping to ease their concerns so that you can get your life-changing solution into their hands.

That’s why you should ask for the sale over the same channel you’ve been talking to them all along.

Step 5: Choose your words wisely when asking for the sale.

Now, it’s time to actually ask for the sale. But don't just ask:

“Do you want to buy the product?”

You spent a lot of time earning their trust. If you’re nervous that how you ask for the sale will compromise the work you’ve done, this is a sure-fire way to turn your fears into a reality.

Instead, you need to find the right words to do it. This depends on a number of things, like what kind of person your prospect is and which sales closing tactic makes the most sense.

Let’s say your buyer is a confident go-getter. She’s always full of questions whenever you meet and she’s expressed enthusiasm in bringing change to her organization.

In that case, it would be a good idea to frame this question in a way that puts the ball in her court. For example:

“What do you think for next steps? Are you ready to move forward?”

You could also phrase the question so that it emphasizes what a smart decision she's making for her business:

“I know your team has been excited for Phase 2 for months and I don’t want you to have to hold this up any longer. When do you think we can schedule setup and training?”

Let’s say, instead, that you’ve taken charge of most conversations with your lead. In fact, it almost seems like he wants you to do a little hand-holding as this is the first big purchase he’s making for his company.

In that case, you should continue to take charge and just direct him to the sale. For example:

“Would you like my help? I can get you started on [date].”

Or you can take this opportunity to once more spell everything out, reiterate the value of the purchase, and ease any last-minute fears he has:

“So, Product A and Product B both include [list the non-negotiable specifications you discussed]. Based on where you’re projecting your business to be in six months, though, I think Product B is where you should start. It’ll do X, Y, and Z, which will enable you to be exactly where you need to be in December.”

You might also have a prospect who’s somewhere between the two that’s been happy to let you guide them to the right decision, but has also been an active participant along the way.

In that case, asking for the sale with “us” or “we” language would help reaffirm that you came to this decision together. For example:

“I was thinking that [date] would be a good time for us to get started. That way, we can have things up and running before the holiday rush.”

Or, if you want to take a more assumptive approach, you can hit them with a simple:

“Let’s discuss pricing and find the best plan today.”

Once you’ve narrowed down what kind of approach you need to take, spend some time working on your word choice. is a useful tool for this. It analyzes your old conversations—with this prospect as well as with others—and identifies words that lead to the most wins. You can then infuse your speech with them.

Step 6: Accept that “yes” still isn't a guarantee.

If you find yourself feeling fearful as you approach this question, then you need to ask yourself what the underlying issue is.

Do you see rejection as an automatic failure?

Do you lack faith in your company’s solutions to do what you’ve been promising they’d do all along?

Do you worry that you’re going to ask for the sale the wrong way and blow the entire deal?

Do you feel as though having to ask for something so obvious as a sale cheapens the relationship you have with the prospect?

Do you feel like there’s too much pressure to always get an instant “yes” because you’re the sales manager and your team is looking up to you?

Fear is a great de-motivator, but you shouldn’t let it be.

Before you do anything else, you need to accept that there’s a risk that the prospect will turn you down. In fact, they might do it a few times.

If that happens, it’s okay!

Don’t take the “no” or “maybe” or “not right now” personally. And don’t let the possibility of rejection scare you from asking.

You’ve fostered this opportunity through a long sales pipeline and wouldn’t have asked for the sale if you didn’t know that the solution was 100% right for them. It usually takes a few tries to get a firm “yes” from prospects anyway, so keep at it.

Ask for the sale with confidence.

What’s great about this approach is that the more you do it, the more you’ll become confident in popping the question because you’ll notice a trend: if you lay the groundwork and focus on building trust along the way, the sale is going to be easy. And asking for it will only make it happen faster.

Plus, if the prospect turns you down, that’s fine. You know what the next steps are.

If they gave you a shaky “no,” follow up and see if you can change their answer to a “yes” down the road. If it was a firm “no way,” drop it and move on to another prospect. It’s as easy as that.

As you master the ability to ask for the sale and demonstrate it for your team, just keep reminding yourself:

There’s no point in dancing around the final question. The sooner you get it out, the sooner you can take action.

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