When and how to challenge your prospects?

If you are in sales, you might already know this: there is usually a big difference between what most prospects say they want and what they actually need.

If you believe the old adage that “customers are always right,” you will never be able to fully understand your prospects. It’s one thing to believe that customers come first, but believing everything they say—without trying to understand the rationale behind it—can be misleading.

It’s what helps them have deeper conversations with prospects, earn their trust, and go to great lengths to uncover insights that others usually fail to do.

In this post, I will share my thoughts on why challenging your prospects is a business advantage, when to challenge your prospects, and how to do it. If you want to level up your salesmanship and improve your close rates, read till the end of this post.

If you would rather watch or listen to what I have to say, tune in to this episode of The Modern SaaS Podcast where I discuss this topic at length with my marketer colleague Yaag:

Challenging your prospect isn’t a bad thing

The word “challenge” often carries a negative connotation to it—especially in business circles. When you hear about salespeople “challenging the prospects,” the first image that pops into your head is about having a confrontation between the buyers and the sellers—some sort of hostile exchange of words.

Let me assure you—it’s not what I condone. In B2B sales, you typically challenge your prospects to dig a little deeper than what you heard on the surface so that you understand their real problems, and not the symptoms.

The concept of challenging your prospects to open up more has been around for a while, but it became more mainstream when two sales experts expounded the concept in their 2011 book The Challenger Sale. In the book, the authors argue that the Challenger salespeople have an unparalleled advantage in controlling the sales conversation and offering a sales experience that extends to customer loyalty.

Why is challenging your prospects important?

Every salesperson should have the mindset, and develop the skill, of challenging the prospect. Salespeople should be naturally curious: anytime a prospect makes an intriguing statement about their business or your product, you should challenge them as to why they think that to be the case.

As a salesperson—you should be driven, willing, and capable to challenge your prospects on:

• Why are they asking what they are asking?
• What is it that they are actually looking for?

A big part of challenging your prospects is to control the narrative from the get-go. Challenging them lets you set up a rhetorical contract upfront to let your prospects know that you are going to ask certain things in return (mostly information) to each ask they will have from you. This is an ageless rule of give-to-get reciprocation that helps you make sure that you and the prospects get where you want to be.

The other advantage of challenging prospects is your ability to push through indecisions and inactions—mostly on the buyer side. Indecision is the worst enemy in sales. Challenging your prospects helps you test them and pushes them to move a conversation in the right direction. It helps you understand: are they getting you to the right place or person?

If you don’t challenge your prospects and dance to their tunes, you are going to end up “playing fetch.” It’s a phrase we use in sales to imply that you are being a “Labrador rep”—you’re just too nice to your prospects and play along with all of their requests without expecting anything in return.

I was guilty of playing fetch with prospects a lot of times early on in my career—as are several young sales reps today. The customers throw the ball—such as asking for an extended free trial or a feature request not available in your product roadmap—and you run as fast as you can, as frequently as possible, to get them a favorable response because they are engaging with you.

In reality, B2B sales is a trade-off between the buyers and the sellers. The problem with playing fetch is that the prospects will eventually stop playing the game with you. They might stop engaging with you the moment they find what they were looking for—leaving you to wonder why they stopped engaging despite your eagerness to answer all their questions.

If you don’t want to be that Labrador rep, apply the give-to-get formula. Really well-trained sales reps will play fetch with customers only if they are getting something in exchange for the value that they are providing to the prospects.

If the prospects are asking for a product demo, that’s fantastic. Tell them that in order to dedicate the sales and engineering resources for the demo, you first need answers from them on what their software buying process looks like in their organization. Better yet, ask them to give it to you in writing.

Closure is one of the best benchmarks in sales—and it doesn't mean that the outcome has to translate into a purchase. It can be many things like the prospects signing a master services agreement (MSA), getting the buying approved by their legal desk, or shaking hands and being on each other’s radar even if the conversation doesn’t end up in sales.

But if you don’t push for a closure somebody else will—either the customers or one of your rivals.

Earn the right to challenge prospects

While you should challenge your prospects at the right times across the sales process, the key is to first earn the right to do so. To challenge your prospects, you first need to really understand:

• The industry you are selling into
• The problems people in that industry are facing
• Each buyer’s business environment

Remember that you are not challenging them to be combative—you are challenging them because you want to give them a better outcome. Therefore, challenging them needs to come from a place of trust.

Before you even start going through the process of prospecting, you need to build a deep understanding of the industry and who you are selling to. It’s why researching your prospects and their industry is a critical component to building rapport with them—especially in today’s remote selling world.

You also have to develop a knack for understanding each buyer’s situation. Every buyer is different—and so are the nuances in their business environments. You can’t bucket a prospect into everybody else that you are selling to.

In advance selling territories, you usually have a target strike zone and a list of customer accounts that you are supposed to go after. Of course, many of them are going to have overlapping similarities if you have already figured out your product market fit. But most buyers usually have subtle nuances to their business use cases and things that matter most to them.

Researching each buyer as a non-negotiable process of your prospecting technique will help you understand those subtleties before you even establish a connection with them. Research is what will help you lean hard toward discovering pains, obstacles, and inefficiencies—as opposed to “feature vomiting” the salience of your solution.

In contrast, there’s nothing that turns someone off faster or makes them slam the rhetorical door on your face than them sensing:

• You don’t know what you’re talking about
• You don’t understand the problems they are trying to solve
• You don’t understand their business, who they are, and what they are doing

If you don’t understand your prospects and their business background well enough, steer clear of challenging them. It will ruin your relationship with customers and earn a bad rap for your brand.

How to challenge prospects across different stages

The short answer is—all the time. Challenging the prospects is beneficial at every stage of the sales process—regardless of what you are selling or who you are selling to.

For the ease of understanding this concept, let’s break it down chronologically. Most sales processes (even inbound) officially start with prospecting and end as a deal lost or won. So let’s start with the prospecting phase first.

Challenging buyers at the prospecting stage

At the prospecting stage, you are just establishing a connection for the first time with a target customer. Unlike in marketing, you don’t have a long nurture time in sales prospecting. The amount of time you have to talk to prospects and get their attention is very short, yet its impact is way too outsized compared to marketing.

It’s doubly challenging to challenge your prospects at a stage when your main focus is to build rapport with them and explore the possibility of booking a meeting with them. Add to that the new complexities that all sales teams face these days—the fact that most buyers do a ton of research and have access to a wealth of information about your product and the competition.

At this stage, the best way for you to make your interaction count with prospects is to bring value to the conversation. Make an effort to offer something valuable to them that they can’t unearth on their own.

If you fail to add value to your prospects, if you can’t position yourself as a trusted advisor to them—you are not going to get two seconds of their time. But if you do, the prospects will be moved and compelled to pay attention to what you are saying.

One way to add value to the conversation is by challenging them to think about something that might not have crossed their minds. Here’s an example of how we challenge prospects to think about the time-wasters in their selling process:

A word of caution: don’t challenge prospects for the sake of challenging. You don’t want to be combative—especially if you are talking to them for the first time. The idea to challenge prospects is to see if they are willing to engage in a conversation, get them to respond, and explore if there’s a match between what you are selling versus what they need.

In outbound prospecting, most SDRs are desperate to book meetings with prospects. You’re eager to get anyone on the phone and it’s practically unheard of for SDRs to turn down meetings.

I’m of the school of thought that you should definitely turn down meetings if the prospects aren’t willing to discuss their requirements in detail before the next step. As an SDR, your goal isn’t to get meetings—the real goal is to understand what the prospects are trying to accomplish. Not every person that picks up your phone or replies to your email is the right buyer for your solution.

Therefore, booking more prospects meetings for the sake of booking meetings shouldn’t be your goal. Instead, your goal should be to legitimately curious to find out—what problems is the prospect trying to solve? In the prospecting stage, you should be 100% focussed on discussing your prospects’ issues as opposed to talking about your solution.

If you can’t add value to the prospects or if you feel that they aren’t genuinely interested in your solution, don’t take the meeting.

Personally, I have seen a lot of success in prospecting by turning down meetings that didn’t hold any promise—both for the prospects as well as for me. On the other hand, meetings that show signs of benefits for both parties—where the prospects were willing to engage in a meaningful two-way conversation—are more likely to actually convert into actual customers.

Challenging buyers at the discovery stage

At the discovery stage of the sales cycle, you know the account a little better than you did at the prospecting phase—and vice versa. Even if the account came to you via an inbound channel, the prospects know your brand or have an assumption of what your product solves for. Challenging your prospect at this stage is similar—but, of course, there are a few nuances.

In prospecting, you are trying to find the right kind of company and the person willing to have a conversation with you. With discovery, you already have that person identified to talk to. Now it’s a matter of going multiple levels deeper. At this stage, you need to dive deeper and find that third level of pain as opposed to scratching the surface during the prospecting phase. Luckily, the discovery stage also allows you more time than you usually have in the prospecting stage. 

During the discovery phase, you have the advantage of uncovering another key insight i.e. the prospect’s perception of your product or the brand. We already touched upon the fact that buyers today come to the sales table after doing a ton of research. It usually means that most prospects have made 60–70% of their buying decision—or at least what they think is their decision.

The bad news is—most prospects have a perceived understanding of what they want and what your product can do for them. The good news is—you can challenge them to change this perception.

In short, the discovery stage lets you:

• Identify your prospects’ perceived problems
• Uncover the real problems
• Lead them to the right solution

Here is a real-life example to understand this process better. At Avoma, we have a twin-engine go-to-market (GTM) motion: a powerful product-led GTM supported by frequent sales touches along the way. A majority of our inbound prospects test drive our 14-day free trial and use Avoma before they come into contact with sales.

This gives them the opportunity to create several perceptions about Avoma’s possible use cases, how they think the tool works, and how it fares in comparison with other conversation intelligence tools.

Some prospects can fully understand Avoma’s capabilities—their perception of the product is usually spot on. But most others get it wrong—without even realizing that they are wrong. They think that they know what they need, but there may be gaps in their understanding of the possible use cases, Avoma’s capabilities, and several things that remain hidden in their blind spot.

As a salesperson, it’s your job to understand the prospects’ perception and challenge them to think about it in a better way. The discovery stage is a perfect opportunity for you to ask pointed questions to your prospects and get a grip on their perception.

Sometimes, it so happens that you might discover the prospects’ pain points that don't align directly with the solution you are selling. In such situations, you have to build a narrative—not in a deceptive way, but in a way that expands your prospect’s horizons.

For instance, most prospects who we qualify for discovery calls often evaluate Avoma alongside other tools such as Gong or Chorus. Both of these tools have great capabilities—but both of them offer features that cater mostly to sales leaders and managers i.e. coaching. Therefore, the prospects have a preconceived notion that Avoma should solve their coaching use cases on part with these tools.

They haven’t thought about or deliberately haven’t built features that can help other buyer personas in sales such as SDRs and AEs—who are equally (if not more) critical to revenue operations. Avoma is broader in its approach because it offers capabilities that don’t just empower sales leaders and managers but everyone who contributes to revenue including SDRs, AEs, and CSMs.

When we are running a discovery call with a prospect, we obviously don’t feature-bomb Avoma to highlight the above point. Instead, we train our reps to ask questions that talk about pain points that Avoma solves. For instance, we might say, “I understand that coaching is a priority for your business to improve sales efficiency. But imagine this for a minute—what if your reps could improve their productivity by up to 50% if you empowered them with a tool that doesn’t just help with coaching but automated meeting templates, note-taking, and playlist curation?”

This sales technique is like leading the witness or sending them down a funnel to think about a problem they didn’t know mattered to them. That way, you can position your product naturally into their business use cases.

That’s pretty much everything you need to know about the difference between challenging buyers during the prospecting stage versus the discovery stage. However, there’s a loop that we need to close to understand how to get multiple levels deeper to find the third level of pain that you can’t discover in casual conversations.

How to find your prospects’ real pain points?

Finding the core pain points that your prospects are going through requires you to dig deeper beyond what they are saying at a higher level. It’s a process similar to the Jobs To Be Done (JTBD) framework—but applied to sales.

In JTBD interviews—mostly employed by product teams—you ask a series of questions to the users of your product until you identify the one core job that they “hire” your product to do for them. Here’s an example from Snickers—the candy bar company.

When Snickers applied the JTBD framework in their marketing research, they discovered that consumers didn’t buy their product just because it was tasty, cheap, or nutritious. Most bought it because it satiated their hunger—and that became the mainstay of Snickers’ viral ad campaigns.

I explain this to our sales rep by offering a fictitious example based on my life. Let’s say I come home from a game of golfing on a Sunday afternoon, looking all grumpy. My wife senses my mood and asks me why I looked cranky. And the first thing I might say is that I’m upset because I lost the game against my buddies in golf.

But because she is such a good people reader, she asks me again if it’s actually my loss in golfing that’s making me upset…or something else? At that point, I might say that it’s not just golf but the kids are driving me crazy too. She might prod further and ask: why are the kids irritating me? What about them is making me upset?

Finally, I give in and reveal that I’m stressed out because I’m worried about not hitting the quota at work or the project that’s due at the end of week. And that’s the third level of pain—the actual reason behind my grumpiness that I took time to reveal. It started from a surface-level pain—i.e. me losing in golf—but it’s rarely the real reason.

The message here is that in sales, you always have to go three levels deep. But it’s easier said than done because you’re meeting most prospects for the first time. It’s why you have to be really good at building rapport with strangers. I actually joke about turning on the rhetorical light above their head—like in a movie where a cop interrogates a suspect—before I start asking them deep, probing questions. Most of them appreciate the joke because I tell them that they can do the same and ask me questions after I turn off the lights.

The point is, most prospects will answer your questions that don't mean anything—not fully. For instance, when you ask them “Why do you need a new sales meeting management software”, they might say something like, “Well, because my salespeople are wasting too much time organizing meetings and analyzing the data manually.”

An average salesperson’s first instinct will be to take the answer at face value, note down the response, and move on to the next question.  A salesperson worth their salt won’t stop there—they will ask the prospects:

“Tell me more about that. Why are your reps spending so much time in meetings? How is it impacting your business? Why does that bother you?” 

To that, they might say, “Because it means they have less time to sell.”

And when you follow up by asking, “What kind of impact does that have on your business?”

Then they might finally come around and admit, “If they are spending a lot of time doing non-sales activities, it means they have less time to hit our revenue numbers.”

And that’s how you quantify your prospects’ pain. In essence, you are not settling with the symptoms that your prospects are communicating but trying hard to understand the pain that’s causing the symptoms.

This process isn’t about not believing what they have to say. It’s more about the prospects giving you a piece of teaser information that you have to keep scratching on the surface to discover the ultimate problem.

Challenging them this way also helps you find something that you can tie back to an ROI or build a business case for so that you can position your product’s value strategically against the pains that you have quantified.

Dealing with deals that aren’t moving forward

Like we discussed earlier, indecision or inaction on the prospects’ part is the biggest giveaway of a stalled deal that’s not worth your time.

There’s an art and science to selling. There are really successful salespeople who apply 80% art and 20% science in their selling and there are others who are 80% science and 20% art. The latter are not natural-born salespeople—but their sales processes are just too good.

Naturally good salespeople usually have some sort of sixth sense that helps them recognize deals—or prospects—that are not moving forward. But you can’t always rely on your intuition to guide you in such situations. You have to follow a scientific approach to identify dud deals.

For instance, you have to test the prospects to see if they can mobilize the deal to the next level. You have to identify if they are going to be the champions who are going to help you move the deal forward. You have to identify who is going to buy, do they know how to buy, or if they can put you in touch with the decision-makers.

Sometimes, it might seem like you are trying to bypass your first point of contact to speed up the deal. You will have to be careful with that because nothing will get the doors slammed on your face faster than trying to bypass prospects for the urgency of closing a deal. It will only burn bridges and ruin your relationships with customers.

Instead, you should position your ask as something that’s mutually valuable. For example, if you know that their VP of Sales needs to be involved in the process for approval, you can say something like:

“It’s great that you are interested in our product demo—and I’ll put that on my calendar as a priority. You mentioned that you would need to run this by your VP of Sales for approval. In that case, can you get me a meeting with him so that I can put together a business case to present to him?”

Notice how this request makes it look like it’s about them and not entirely about you? You are showing value in the request instead of just asking for a meeting to be set.

If you challenge them on these fronts and you sense a lack of decision-making or innovativeness—it’s a sign that you should abandon the deal for something worth your time and effort.

A lot of reps that I see in B2B sales spend close to six months in a sales cycle with a director-level person playing fetch and eventually losing a deal. And when their managers ask them why they lost the deal, their response is, “Their CRO was friends with this other company that they were evaluating on the side and I had no idea that was even happening.”

The fact is, they lost the deal because they were wasting their time talking to people who weren’t mobilizing the process to move to the next level.