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Everything You Need to Know about Gap Selling

Everything You Need to Know about Gap Selling

Kushal Saini Kakkar
Kushal Saini Kakkar
January 17, 2023
5 min read

We’ve all heard at least one story about a silly salesperson barking up the wrong tree. 

The lady who tried to sell hair smoothening shampoo to a bald man. 

The connoisseur who tried to sell a crate of wine to a recovering alcoholic. 

The tele-caller who tried to sell the whole volume of encyclopedias to old Mrs Robinson, who can’t see very well anymore because of her glaucoma. 

It happens to B2B SaaS companies too. There’s a story about a software company that put construction blueprints on tablet computers without thinking about current state versus desired state. If they’d used gap selling, they might have found out that toting delicate glass objects that need frequent charging around a construction site was not the desired state of their prospects. 

What happened in the end

You’re probably smiling broadly at your own memory of a similar story you’ve heard somewhere.

Or cringing inwardly if the silly salesperson barking up the wrong tree was you. It's okay! You’re wiser now.

All of the examples we just looked at are situations where a gap-selling approach might have helped the salesperson avoid wasting their time. 

Gap selling is a sales methodology developed by Jim Keenan (who actually goes only by his last name, Keenan). Keenan is the author of the best-selling sales books Modern Gap Selling and Not Taught. He is also President & CEO of A Sales Guy Inc and A Sales Growth Company

Keenan has a post on LinkedIn that says, “Sales is not about relationships. Salespeople need to stop spreading that myth. If I hear another salesperson say to me sales is all about relationships, I’m gonna lose it. I don’t need any more relationships.” 

No more of the "please like me" sales game

Keenan seems to believe that sales is less about making friends and more about making product value abundantly apparent. And you’ll see this clearly in his gap-selling methodolgy. 

So what is gap selling?

Gap selling is a problem-centric sales methodology. Not to be confused with a sales process.

Gap selling is developing a thorough understanding of the prospect’s current state and guiding them to a future state that they find desirable. You need to find out what troubles your potential customers about their current state, and you need to find out (or be able to gauge) what the prospect’s desirable future looks like. 

Suppose you sell a mobile app for smoother accounting and your next sales call is with Prospect A. Let’s try the gap-selling methodology:

You ask Prospect A what their accounting obstacles and general revenue-related struggles are. Prospect A says that his team is struggling with erratic cash flow and frequent late payment charges that stem from lacking visibility. They don’t have an at-a-glance view of accounts receivable and accounts payable. They tend to receive invoices late and send their own invoices late. 

Prospect A’s desired future state might be to at least send invoices on time (so that they can ask for on-time payment) and better visibility of payables and receivables. 

With these two pillars in hand, a smart sales rep is able to sell based on the gap. Your accounting software can bridge the gap with easy-to-use dashboards that will give Prospect A better visibility – that’s exactly what you will say in your sales pitch. 

We could hear the F.R.I.E.N.D.S. fans go: “Aaaa, salmon skin roll…”

How does gap selling work

In the example above, you did not talk to prospect A about your product until you had a clear picture of their current state and their desired future state. 

It is crucial to stress that the discussion of the prospect’s problem takes place before the sales rep mentions a product.

If you’re wondering, “But what if the prospect just says they’re all good,” you’re on the right track. Prospects might indeed say they have no pain points and effectively shoo you away.

But Keenan probably foresaw this. That’s why the gap-selling methodology comes with a set of questions, or more precisely, three sets of questions namely: probing questions, provoking questions, and validating questions. 

Gap selling questions

All three categories of gap-selling questions are discovery questions. You’re already habituated to using discovery questions during early conversations with prospects, so these are not going to be challenging. 

Probing questions

This list of questions is the equivalent of laying a foundation. You start by understanding your prospect’s situation and mindset. You want to figure out their pain points but also the root causes of their problems. Here’s what you will ask your prospect: 

  1. What are your biggest business problems, obstacles, or challenges? 
  2. What is working for your organization, and what isn’t working? (Just in case they say that they have no problems.)
  3. Do you think there is any tech out there that can solve your problem/ fast-track your business goals? How? (Just in case they tell you everything is working just fine and start making for the proverbial door.)
  4. How does <mention process related to problem> work now and how would you prefer for it to work? 

Provoking questions 

Sounds like you’re trying to make them mad, doesn’t it? Well, you are actually trying to make them mad. Not mad at you, but mad at their current situation, and therefore open to a more desirable situation with your product or solution.

Provoke them into kicking their current state in the face

Ask these questions to get your prospect thinking: 

  1. Have you ever thought about trying <mention your product/ product category>? / Have you tried  <mention your product/ product category>? 


Have you thought about what would happen if <mention a top feature or benefit of your product that bridges the gap>

  1. What is the impact of those problems the rest of the team and your revenue goals?

Validating questions 

Here you’re making sure you got things right. Any useful discussion about problems is going to have multiple pain points stated and several examples. It will often go on a tangent or two and have some overlapping and confusing elements. Validating questions help you to ensure that you have understood the prospect's current state and ideal future correctly and thoroughly. Not because the prospect is your new BAE or BFF, but because you’ll be basing your sales pitch on their current state and ideal future state. 

You need to get a definitive answer here, so asking closed-ended questions works best. Ask questions like: 

  • If I have understood correctly <insert problem/ undesirable elements of current state> is your main business challenge/ obstacle/ problem, right? 
  • When we spoke last week/ month/ quarter/ time, we talked about how you were struggling with  <insert problem/ undesirable elements of current state>. Is that still a struggle for you or have things gotten better? 

You might be able to answer some of your own questions with a quick research on LinkedIn and B2B news and features websites or newsletters. If you read that XYZ company says its biggest struggle is manpower in new markets and you sell some sort of talent discovery service, you know how to get your foot in the door. 

When your pitch shows how your product bridges the gap

Why try gap selling?

Earn more per deal 

Gap selling is the best way to command a better price for your product. If you feel like you’re always settling for a lower-than-optimal rate to close deals, it is possible that you are struggling with displaying value. This is not a failure on your part. The market is competitive, and prospects will always try for the best deal. It's human nature to do so! 

Besides, they have the upper hand. You need them because you need to meet your sales quotas. They don’t need you.

Or do they? 

According to Keenan, they do! Prospects do need you. 

If your prospect has a wide gap between their current state and desirable state, your prospects need your product. And the point of gap selling is to guide them to the realization rather than to try and feed it to them. 

Here’s what Keenan has to say about slashing prices to close a deal: “The reason you lose on price is that you have no leverage. There is no reason to keep losing on price or lower your price, just because the buyer says so,” he says on his LinkedIn.

The leverage he’s referring to is your product’s ability to overcome the customer’s problems and help them achieve their desired future state. 

Become a trusted advisor 

The second lot of gap-selling questions, that is, the provoking questions, are aimed at getting the prospect thinking about the gap between their desired state and current state. You want them to arrive at the value of your product almost independent of any sales nagging. The idea of allowing them to arrive at realizations by themselves (with only innocent questions from you) is that they’ll see you as a trusted advisor rather than be suspicious of you. 

Get all the leverage you need with Wingman 

Wingman is yours sales BFF 

Gap-selling is all about developing leverage. Wingman helps you ace gap selling and develop leverage with far less effort.

For example, when you’re about to make a follow-up call to a prospect, Wingman’s pre-call customer profile can come in handy to revise and recall the prospect’s background and problems. Wingman’s call recordings, call summaries, and transcripts help you to browse through your conversation with a fine-toothed comb so that you never miss a problem statement. 

Monologue alerts ensure that you are letting prospects detail their situation to you by telling you when your talk: listen is skewed or when you’re not letting the prospect express their current state and desired state. 

Easy CRM integration means that you’ll have more time for asking the right questions and actually selling rather than typing in details.

Wingman gives you more time for selling (and sleep) by cutting your admin workload


Sales leaders, if you have expert gap sales stars (or challenger sales stars, or SPIN sales stars) on your team, how about having the whole team learn from them? Share recordings of winning sales call with the rest of the salesforce. 

Wingman is just what you need to make sales management and sales training easier. You can review the sales team’s calls quickly and easily with 2X speed and search for relevant keywords. You can also try muting other speakers to focus on your rep or the prospect. You also get at-risk deal alerts when competitors are mentioned or pricing is not discussed. Success metrics let you create sales forecasts rooted in reality. 

Wingman helps you achieve your desired state as a confident salesperson, armed with useful tech. Or an efficient sales leader, armed with all the resources to help their team win.

Try it yourself. Get a free demo today. 

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