The 10 Best Sales Questions To Increase Your Close Rate

I’ve been on more than 10,000 sales meetings over the past 20 years. I typically get involved when the prospect is well qualified and we’re putting together and presenting program recommendations.

But even at the end of the process, opportunities still exist to ask excellent questions that get the prospect to share important information that helps the sales team manage expectations and get the deal over the finish line.

While most articles focus on the qualification questions at the beginning of the prospect’s buyer journey, I think these questions toward the end of the buyer journey are even more important.

Here are the questions we use to get over the finish line and turn sales opportunities into new clients for Square 2 and help our clients turn their sales opportunities into new customers, new revenue and business growth.

These are in no particular order, and I’ll provide context and commentary as to why and when I like to ask these questions. Also, I like these questions because the salespeople rarely ask them.

1. How big a priority is this project for your company on a scale of 1-10?

I think salespeople are afraid of the answer with this one, so they don’t ask it. It could be asked earlier, but again, salespeople assume that if prospects are talking and taking the time to work with them, the project must be a priority.

I like asking this when several decision-makers are on the call to ensure everyone is on the same page.

I also like pushing them for a number, and I might follow up with an additional question as to why they gave the score they did. This almost always uncovers how important this project is and ensures that everyone on the decision-making team is on the same page with the stated priority.

2. What are some possible outcomes if you don’t move forward with this?

This is a great question to get the prospect to start thinking about the consequences of NOT doing something with you. It might be the first time they even considered what might happen if they don’t move forward or move forward too slowly.

Making people say things out loud is an important tactic. If they say it, it becomes real.

Sometimes it might seem obvious, but talking about it allows you to dig deeper and uncover other potential outcomes that are also worth getting out on the table and discussing.

3. What’s the decision-making process after this final meeting?

I don’t think reps like this question either because it has the potential of including an answer that they might not want to hear or not be prepared to deal with.

Reps often find out that who they thought was a decision-maker is actually not the final decision-maker.

For example, if the decision includes the board and you won’t be invited to that session, you’ve lost control of the process. Anything can happen at that board meeting, and negative outcomes are common.

We often request to be included in additional meetings or conversations. While we’re often rebuffed, it’s not bad to ask and offer to help communicate to other parties to help your contacts get their project done.

4. What other options are you considering to solve this challenge for the company?

Everyone has options. It might look like your recommendations are a slam dunk, and your contact might even be telling you it’s a “done deal.” But there are always alternatives. In some cases, doing nothing is the safest option.

By asking, you get to hear what they’re considering, and you get to participate in some of the discussions around alternatives.

They might be considering hiring in-house, bringing in other partners, doing a smaller project or pushing the work off three months.

You have to know what they’re thinking so you can best position your solutions, customize your recommendations and help them make a good decision for their business — whether that includes you or not.

By knowing what they think their options are, you get a good idea of where you stand in the order of possible options for them going forward.

5. What is your time frame for making a decision and what are the implications of this getting extended?

Timing in sales is important. Reps have numbers to meet each month, and forecasting should be an exact science. But if you don’t ask about the time frame, your assumptions might be wrong.

Most reps think that once they get to the end of their sales process, the deal is about to close. That’s not accurate.

The prospect’s buyer journey is the only timing that matters. Often, prospects still have several stages to get through once you present your final recommendations.

They have to rationalize the information, they have to make a decision, they might have to reach a consensus with other decision-makers and they might have to get the budget approved or allocated.

Asking specifically about timing should uncover the actual timing and process still needed before they can give you the final “yes.”

6. What were you expecting to invest to solve this challenge for your company?

This is actually my favorite question. Sometimes it might take this form: “What did you budget for a project like this?” But since so many people are either uncomfortable sharing budget data or are actually honest when they say, “We don’t have a budget for this project,” I’ll change the question to get around the budget issue.

Everyone has expectations about what things cost. When you go to the market and buy orange juice, you expect it to be around $3. If it’s less, you feel like it’s a good deal, and if it’s more, you might consider not getting it or looking for it somewhere else.

When you get an estimate on your kitchen remodel, you have an idea of what you think it should cost and what you want to spend.

Everyone has an idea or expectations around what costs are required to purchase products and services. Every one of your prospects should be able to answer this question regardless of budget.

Once they do and share it with you, you’ll know roughly the range and level of investment and whether you can get into that range.

While it’s good to ask this early, I think it’s better to ask this question a few times during the process. As you get into it, the scope might expand and the investment with it.

The more you align on investment and cost, the less surprised the prospect will be at the end when you reveal your required investment. Surprise is something you want to eliminate completely from any sales process.

Prospects who are surprised don’t feel safe, which usually means they don’t buy.

7. What are your expectations for this project over the next 30 days, 90 days and year?

This is also one of my favorites because it quickly aligns what we think we can do with what the prospect expects us to do. You need 100% alignment to have a happy customer.

If their expectations are too high, it’s an opportunity to talk it out and help them understand why. If their expectations are too low, that’s an opportunity to educate them on what you do that should produce better than expected results.

Either way, it’s a very productive conversation that should align both sides around what you’re going to do and the expected results or business outcomes.

If alignment isn’t possible, then this is an opportunity to end the process and move on to another opportunity where alignment does exist.

Doing business with a company when you know you can’t deliver to their expectations is a mistake that could haunt you for a long time.

8. Are there any concerns we didn’t discuss that would prevent you from moving forward with us and our recommendations?

I like this question because it gives them one more chance to share any concerns or issues with you before you wrap up and encourage them to make a decision.

Once you ask this and they respond with “no,” you can be confident your sales process provided everything they need to make a good, educated and safe decision.

If for some reason something was missed, this is their opportunity to mention it and for you to answer it or handle it before they go into decision-making mode. When the meeting is over and they’re discussing their options, they shouldn’t have any concerns about you, your company or your products/services.

Not all your competitors will ask this question.

You want to uncover as many unknowns as possible during the sales process, and questions like these do their part. You can’t address what you don’t know, and if you ask the right questions, there should be very little you don’t know.

9. Have you worked with any other firms like ours in the past? How did it work out? What did you like about it? What didn’t you like about it?

This is important, but honestly, I don’t ask it every single time because almost no one likes to answer it. Some people feel like they’re airing dirty laundry or that the past is the past and it’s best to move forward. I get it – all good as far as I’m concerned. 

But when they do answer it, you learn a lot. You might uncover a pattern of behavior that will make it difficult for you to be successful with them. 

Something they hated might be something you do often. Something they loved you might not do at all. Hopefully, something that was a challenge for them allows you to talk about how you do that differently and in a way that is aligned with how they want it done. 

Knowing what went wrong in the past helps you navigate around this and ensures you don’t make the same mistake as the last company. Knowing their expectations in these areas clarifies whether you can do what they want.

10. Your feedback is critical to us working together productively, so can you share some with us now? How did we do during our sales process? 

This might be very specific to us, but one of our core values is Every Client A Raving Fan, and we have a process around advocacy that backs this up. However, prospects aren’t part of this process, as you might imagine.

But we want to know how we did, and we use this core value as a way to ask the question, “How did we do during the sales process?” It allows us to introduce the idea that we are going to be asking this question frequently.

Prospects like this and enjoy getting the opportunity to share feedback around their experiences during the sales process. Most of the feedback is very positive, and getting them to talk about this helps us solidify our company as one of their top options.

It also helps them reflect over the course of at least a few weeks and reminds them of the multiple calls we had, the many questions we asked, how good we were at listening to them and how customized our recommendations were to their organization.

When it comes to our competition, we stand out. Most companies deal with a sales rep who asks a couple of questions and then gives a packaged set of recommendations in a templated proposal.

When it comes to Square 2, we’re more like the experience you get at Mercedes versus the experience you get at Chevy. Of course, this is by design, but prospects like it and it helps us close faster and more frequently.

Consider these questions for your sales process. But more important, look to build out a sales process that differentiates you from your competition. There may be several places where your sales effort needs some upgrades.

That’s the secret to closing more new customers faster and closing them more frequently.