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February 23, 2023

Uncovering a Prospect’s Pain: How to Improve Your Sales Team’s Questioning Skills for Greater Sales Success

In today's hyper-competitive market, sales professionals must leverage their soft selling skills to ensure continued sales success. In our last article, "Increase Sales During a Recession with Emotionally Intelligent Sales Teams," I outlined how important it is to build emotionally intelligent and resilient sales teams to hedge against falling economic conditions.

In this article, I want to focus on the soft skills required to improve your sales team’s questioning skills.

Questioning skills involve being able to ask the probing questions required to identify a prospect’s pain points. Simply put, if your sales teams can improve their questioning skills allowing them to consistently discover and understand the challenges that prospects are facing, there is a much greater chance that those prospects will end up writing you a check.

Neil Rackham, the author of books such as "SPIN Selling" and "Major Account Selling," has extensively researched why prospects buy. His investigation shows that close ratios increase as much as 50 percent when salespeople discover a prospect's pain and can effectively illustrate its impact and implications.

Why is it Important to Work on Soft Skills to Improve Questioning Skills?

Unfortunately, many salespeople jump straight into presenting solutions without asking enough questions to diagnose the root cause of the prospect's problem. This can result in the prospect feeling bombarded with product pitches and not having their real concerns addressed.

Even the best sales professionals can get excited during the sales process, going all in on the buying signals without any evidence that the prospect’s problem is real enough or big enough to fix. As I often say, emotions started running the meeting rather than good selling and influence skills.

When salespeople leap before they listen, everyone loses.

Emotional intelligence skills such as impulse control, emotional self-awareness, problem-solving, and empathy can play a significant role in conducting a consultative, value-driven sales meeting that will uncover a prospect's actual pain.

Improve soft skills, and you improve questioning skills. Salespeople will slow down to determine the root cause of the prospect's pain and provide effective solutions.

Uncovering a Prospect's Pain

Use the 3Ws Formula to Improve Questioning Skills and Discover a Prospect's Pain

In sales, it's essential to find your prospect's pain. However, many salespeople make the mistake of letting their emotions take over when they hear statements like "We need to fix this service problem" or "We've got to improve to stay ahead of our competitors."

These emotions can lead to a lack of focus on the sales process, with not enough questions, the right questions, or the tough questions being asked.

To avoid this knee-jerk emotional response,  salespeople apply emotional self-awareness and use the 3Ws formula to slow down, focus on asking the right questions, and uncover the real problem and its implications.

Why is this a Problem?

The first question to ask is "why" - why is this a problem for the prospect? It's important to be self-aware and not make assumptions based on meetings with other prospects, as each prospect's situation is unique.

To get to the heart of the problem, you need to ask questions like:

  • Why is this a problem for this prospect?
  • What is the root cause of this problem?
  • What has been done so far to address this problem?

What is the Current Impact?

The next question attempts to uncover the current impact of the problem. Emotionally intelligent salespeople tap into their problem-solving skills to find the answers to specific impact questions, such as:

  • What is the financial impact to the prospect? (How much is this problem costing the customer?)
  • What is the strategic impact to the prospect? (Is the problem affecting global expansion?)
  • What is the personal impact? (Is the prospect's job in jeopardy?)

What is the Future Impact?

The third question is also a "what?" - but with a spin. It aims to explore the future impact of not solving the problem. What’s really at stake if the problem is allowed to continue indefinitely?

Again, problem-solving skills help sales professionals determine the future impact by asking questions like:

  • What is the future impact for this prospect if they don’t solve this problem?
  • Will it get bigger?
  • How much bigger will it be a year from now?
  • Will it become the problem that brings them down?
  • What is the cost of doing nothing?

By asking these questions and encouraging prospects to think through their unique needs, salespeople can better understand the problem and its implications and help prospects discover the cost of doing nothing.

The key is to control the impulse to tell and solve and instead ask more and talk less.

4 Strategies to Improve Questioning Skills and Uncover a Prospect's Pain

Challenge Your Prospect

Good salespeople ask questions that challenge their prospects to think and look at their business issues in a different light. When a prospect gives you their time, don't waste it. Most prospects expect to be challenged and asked questions that might even hurt their brains

However, it’s important to bring empathy to the conversation to know when, where, and how to ask these tougher questions. Without empathy, salespeople come across as aggressive rather than assertive.

In addition to using the W3 formula, leverage some of these challenging questions to uncover your prospect's pain points in your next sales meeting:

  • Who loses their job if this problem doesn’t go away?
  • Are you looking for a quick fix or a transformation?
  • If you lose market share, how tough will it be to win it back from your competitor?
  • Is your biggest competitor sitting back doing nothing, or are they getting more aggressive?

Get to the Prospect's Real Pain

In the sales profession, the problem presented by a prospect may not always be the real issue. Just like in psychology, good salespeople should use problem-solving skills to uncover the actual problem. This requires impulse control which allows salespeople to be disciplined and methodical in asking good, intelligent questions.

Without impulse control, salespeople offer solutions too soon and too often. By looking at the presenting problem from all angles, salespeople can diagnose the prospect's real pain and create a solution that addresses the real issue.

To improve your ability to identify a prospect's underlying problem, apply the soft skill of problem-solving. A systematic approach to asking practical questions helps you look at business challenges from all perspectives. Better questions produce better solutions. When you take the time to diagnose the actual issue, your solution will be right on target, and your prospect will appreciate your thoughtfulness and attention to detail.

Determine Your Prospect's Commitment to Change

The truth is, just because a prospect shares a problem with you doesn't necessarily mean they are committed to resolving it. Some prospects may want to vent and whine about their problems. It's up to the salesperson to differentiate between a complaint and a commitment to invest and improve.

A good salesperson must manage their emotions and recognize that the prospect may simply be stating a problem, not committing to change. Instead of taking the prospect's word for it, the salesperson should ask qualifying questions to uncover their commitment level to achieving the desired outcome.

A qualified prospect has the motivation and resources to make a purchase, while a suspect may have a problem but lacks the motivation or resources to address it. By getting the prospect to prove their commitment to change, the salesperson can avoid wasting time on proposals for suspects that won't lead to a sale.

Agree and Align with Your Prospect

Sales meetings can be stressful for both the salesperson and the prospect, with objections from the prospect triggering a fight-or-flight response in the salesperson. As a result, salespeople often stop asking questions and start information spewing. However, emotionally self-aware sales professionals recognize this potential trigger, manage their emotions and apply a skill called "agree and align" to manage their emotions.

When a prospect objects, the self-aware salesperson agrees with and validates the prospect's position rather than pushing back. This disarms both the salesperson and the prospect's defense mechanisms and sets the stage for further conversation and questions. It also helps salespeople change their response instead of slipping into fight-or-flight mode.

Empathy and self-awareness are also crucial to executing this powerful selling skill. Both EQ skills help salespeople validate the prospect's position because they are sincerely trying to understand their thoughts and perceptions.

In Conclusion

In conclusion, the inability to ask the right questions and actively listen is a common weakness among sales professionals, leading to missed opportunities and lost sales. Salespeople who struggle with these skills often fail to understand a prospect's true pain points, leading to proposals that miss the mark or price-based negotiations.

Developing a solid foundation in questioning and listening can help sales professionals build stronger relationships with prospects and ultimately close more deals. By practicing empathy and remaining open-minded, sales professionals can gain a deeper understanding of their prospect's pain points, needs, and motivations, enabling them to tailor their approach to meet those specific needs.

Ultimately, effective questioning and listening skills are essential for success in the world of sales. Emotional intelligence helps salespeople master these hard skills, which in turn help sales professionals achieve their goals and build long-lasting, profitable relationships with their customers.


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