23 Powerful Sales Discovery Questions That Close Deals

A well-designed sales presentation is structured to figure out:

1. i) Whether you’re a good fit for your prospective client.
2. ii) Whether the prospect is a good fit for you.

iii) And put in place the next steps for working together.

That’s all. It’s not complicated. But it takes a bit of planning to get it right.

To achieve the above we use intentional questions to propel our sales process in the right direction. When you ask the right questions at the right time, you’ll uncover valuable insights. And build a strong foundation for your client relationship.

In this article, we’ll look at 23 sales discovery questions that will achieve the goals listed above. While also moving the client closer to signing a deal.

Let’s get started!

Why Sales Discovery Questions Are So Important 

For many of us, our natural inclination is to structure our sales presentation in the form of a speech. Maybe with lots of pretty slides to go with it!

While we all appreciate an hour of PowerPoint (right?), this approach doesn’t actually work very well. People don’t like being told stuff; they’d rather discover it for themselves.

And that’s why it’s so important to format your presentation around specific questions. You’re not telling your prospects what you think they want to hear. Rather you’re learning about their challenges and priorities.

Asking the right questions in a logical order helps you keep the discussion organized and focused on the customer. So they’ll feel like they’ve been heard. 

Moreover, the process of gathering information will establish your expertise in your field. And give your potential clients a strong understanding of their own situation.

Combine Open-Ended Questions With Active Listening

The best sales questions are open ended.

Open-ended questions refer to questions that can’t be answered with a simple response. They typically start with “why” or “what” or “how”.

For example, “what’s your favourite movie?” is a closed-ended question.

But an open-ended question like, “why do you like Star Wars so much?” invites a detailed response. 

Open-ended questions encourage sharing what’s really happening in their current situation. And speaking with a 3rd party can provide a different perspective on their business challenges. 

Open ended questions need to be accompanied by active listening. This is where you respond to what is being said. And ask follow-up questions to expand on specific details.

Being an active listener shows an active level of interest in their business. And will usually uncover information that might not have come to light. 

Skip The Pain-Inducing Questions

Pretty much all classic sales literature talks about pain. You can’t sell anything if your prospect doesn’t have a need.

Mostly, it’s true.

But the world has changed a bit since many of these sales tropes were invented. Buyers do deep research before they ever contact a salesperson. They’ve got multiple options and they know all of them.

If they’re reaching out to you, they think you can help. They’ve already clarified the pain. They want to move on to the resolution process.

I once saw the shortest sales meeting. Ever.

Less than 2 minutes from start to end. And no, a deal wasn’t made. This is a cautionary tale.

My friend wanted to improve his (rather poor) website. So he called a web designer and invited them to pitch a new website.

In the first minute the developer emphatically informed him that his current website sucked.

And that was the end of the meeting. 

Sales literature talks a lot about eliciting pain. Don’t confuse that with GIVING pain.

They aren’t the same thing at all.

A lot of the recommended “sales qualification questions” are extremely blunt. And they straddle the line between eliciting pain and giving pain. 

For example, a highly touted sales question is:

What will happen if you don’t fix this problem?

In theory this question will help them clarify the cost of not taking action. But in practice it’ll probably just make them feel bad and insult their intelligence. 

Yes, it’s sometimes effective.

But it’s blunt. And ugly. And it’s not really worth the risk of annoying your prospect.

Instead, ask informational questions that follow a natural line of enquiry. For example,

• • How do you benchmark [X]?
  •  Oh, would you recommend that system to others?

• Are your results aligned with your goals?

Questions like this put you on the same side as your prospect and help them clarify their own specific needs.

Sales Discovery Questions That Establish Trust

Unless your prospect trusts you, no amount of sales genius will result in a sale. Without trust, there’s just no basis to move forward.

So whenever possible, start your sales presentation with a quick summary of yourself and your company. Do your best to address common trust objections that other prospects have shared in the past. 

Use questions to uncover preliminary concerns. And to assure them of your expertise. For example:

• What are you looking for in an [X]?
•  Would it help if I shared a bit about my background?

Notice the second question asks permission to share. You don’t want to start bragging about yourself or your company. You want to share information that is contextually relevant to their answers to the first question.

Pro Tip: Don’t be afraid to toot your own horn a bit. No one else will do it for you!

Sales Discovery Questions That Establish Suitability

Next, your customer wants to know whether you can help them or not.

And you want to know whether they’re a good fit for your solutions. 

Ask open ended questions that explore what they are currently doing. And follow up with questions about where they want to be in the near future.

For example: 

• What prompted you to reach out? Why now?
• What’s your current process for [X]?
• What other approaches have you tried?
• Is [X] working well?
• What do you like about [X]? What could be better?

Note how the questions are phrased around “the process” instead of the individual. The focus is on an external process that can be substituted for another.

Use follow-up questions to learn as much about your customer’s situation and goals.

Be sure to write down the exact words they use to describe the problems they are experiencing. You’ll want to use those exact phrases later on to remind them of what they want to achieve.

Good open ended sales questions will give you plenty of opportunities to share lots of insights that add value. You may not get another chance to speak with this prospect, so you want to make as strong an impression as possible.

Questions That Flesh Out The Deal 

Just as your prospect needs to know whether you’re the right provider, you need to know whether you can deliver effectively

So dig into some questions that specifically explore project execution.

For example:

• When are you looking to start this project?
• From the point of launch, what’s your target timeline for delivery?
• What milestones would you expect to see along the way?
• Who will be involved?
• Will you be the main point of communication?

Discussions about project minutia have a dual purpose. You may uncover possible issues that need to be ironed out.

And discussing the project in this way has the added benefit of ‘assuming the sale’. Every answer about how the project will work assumes you’ll be moving forward with the deal.

Questions To Establish Affordability

Your prospect has three concerns about your solution.

1) Will it work for me?

2) Is this the right partner?

3) Does it fit our budget?

Depending on your solution, affordability questions may need to come at the end. After all, how can you quote a price without knowing what they need?

Personally I like to get affordability questions out of the way as early as possible. If I can, I’ll stick them at the beginning. But that’s usually a bit difficult since it’s hard to quote until you know the specifics of the project.

That said, early on you CAN learn about their average lifetime value per client. This is important information you’ll need to ‘justify’ the cost of your solution.

You should know in advance what constitutes ‘affordable’ for your solution. Often affordability is expressed in relation to something else. And expressed as a ratio. 

For example, if your solution costs $10k, but saves $250K in expenses then it’s a ‘no-brainer’ in terms of affordability. 

No one will purchase your solution if there’s no obvious ROI. So introduce metrics that make sense and everyone can agree upon. Without that common language it’s hard to know whether your solution is ‘worth it’ or not.

Try asking questions like:

• What pricing model are you using? 
• Who will approve the budget for this project? 
• What criteria will they use in the decision process?

The better you can frame your potential client’s definition of affordability (or suitability) then the easier it will be to match their requirements.

The Best Questions To Identify Objections

I once visited a media company as a potential buyer.

Their sales presentation was exceptionally good. And throughout the presentation I made positive, supportive comments.

At the end of the presentation the salesperson was SURE they had a deal locked in.

So they asked me,

“On a scale from 1 to 10, how likely are we to move forward with this?“

Such an interesting question! He was surprised when I replied, “about a 2 or 3.” But it gave him a chance to dig into my concerns and figure out why their offering didn’t fit our business needs.

This illustrates the importance of getting objections out into the open before it’s too late.

Unless you ask, prospective clients will just tell you what you want to hear.

But if you ask, they’ll usually share honest feedback.

So make SURE you ask!

My favourite question to uncover unspoken objections is: 

What potential roadblocks do you anticipate moving this forward?

It’s such a great sales discovery question because it gives your prospect the opportunity to share ALL the things that are going to go wrong. You get a sneak peak!

For example, even though they said they were the decision maker, it turns out others will be involved.

Or their time frame is different from what you expected.

Or they’re in conversations with another vendor.

Or your pricing isn’t aligned with their budget. 

Or new budget won’t be available until next quarter.

And so on.

A million things can derail a deal so it’s good to nail down what’s REALLY happening.

Otherwise prospects will be happy to share encouraging feedback, with no intention of actually working with you.

Another way to isolate objections is to simply ask for the sale in the form of a hypothetical.

For example:

“So just to confirm… If we were to do X [activity & outcome] by Y [time], at a cost of Z [$], then we’re all set to proceed?”

 Summarizing and asking for a deal is bold, but it works. One of three things can happen.

1. You’ll get an agreement and a deal.
2. You’ll get an objection. And you’ll know where you stand.
3. You’ll get a polite yes. Which will evaporate the moment the meeting is done.

Well, like Meatloaf sang, two out of three ain’t bad. 

Next Steps Questions

Oddly enough, objections and next steps tend to go hand in hand. If you don’t flush out the objections, there ARE no next steps. So be sure to do that part first!

Every meeting should end with some next steps that will take place.

Most of the time your prospects will ask you to send them some information summarizing what was discussed in writing.

That’s pretty reasonable, so it’s hard not to agree. 

But what about them? The deal won’t move forward without their active buy-in. So they need to agree to take some action, too. If they don’t agree to a follow up activity then they clearly aren’t as engaged as you are.

An easy approach is simply to book your next meeting on the spot. 

“Next we need to [value oriented outcome]. Does meeting this time next week work well for you?”

Sometimes it works, but not everyone knows their schedule. And it’s hard to know if their reluctance to set a time is reflective of their overall engagement.  

At the end of your call, tell your prospects what you’ll be doing next. Then, ask them to do one or two small things. If they do them, the deal has momentum.

If they agree to your tasks but don’t execute them you’ve got a reason to follow up.

Try and link your follow up tasks to the first stages of the project. It could be something as simple as,

“To get the ball rolling I’ll send you [a requirement] by Tuesday. Can you let me know by Thursday?

The more your prospects talk with you about the deal, the more likely it is to close. 

And if the conversation becomes one-sided, you know you’ve got a problem. 

Your Favourite Sales Discovery Questions?

 How about you? What are your favourite sales discovery call questions? 

 I’d love to hear about your experiences. 

Let’s connect on LinkedIn or send me a note on our contact page.