Your Sales Reps’ Top 3 Questions on Structuring Sales Conversations, Answered

Training Industry / sponsored by Julie Thomas, President & CEO of Valueselling Associates


It happens all the time: Organizations invest significant resources in refining their sales presentations, creating beautiful slide decks meant to facilitate the perfect sales pitch — only to find their efforts ineffective. In today’s business-to-business (B2B) sales environment, pitching takes a distant backseat to forging the authentic relationships that enable sales reps to identify urgent problems actually worth solving. The hard truth is that no one cares how much you know until they know how much you care.

As sales leaders, it’s our job to instill the importance of flipping the script and adopting a prospect-centric approach. People want to do business with people they trust, and people tend to trust people who understand their perspectives and challenges. However, if sales reps are not equipped with an effective questioning process, they’ll struggle to fully understand and connect to a prospect’s unique situation and motivations. Without this knowledge, salespeople can seem like solution providers in search of a problem, when prospects should view them as problem experts, there to accurately position solutions that solve critical business concerns.

How can sales leaders help their teams use targeted questions to connect, build credibility, uncover urgent business issues and synchronize with the prospect’s buying process? Here are the answers to the three most common questions reps have when developing the skills to structure meaningful sales conversations.

1. Which Types of Sales Questions Are Most Impactful?

Salespeople should approach meetings with the intent to engage, especially when selling at the executive level. Not only is asking questions and actively listening the best way to learn, but asking relevant questions that drive the conversation in a certain direction builds credibility and rapport.

You can teach sales professionals to better understand a potential buyer’s perspective, challenges and motivations through what O-P-C questionsopen-ended, probing and confirming questions. When coaching your teams, help them use open-ended questions early in the conversation to help prospects start talking.

For example, if your company sells a manufacturing solution, your sales reps might ask, “How has your supply chain been impacted by A and B?” or, “What are the key performance indicators (KPIs) you’re currently tracking for X?” Open-ended questions should be just that — open. While they’re particularly useful in discovery, sales reps can use them in all stages of the sales cycle.

Once salespeople have identified a point of interest, it’s time to switch to probing questions. Now is their opportunity to dig and uncover critical issues — the kind that likely have the most urgency. Probing questions also help reps direct the conversation and introduce elements that the open-ended questions did not bring up.

Perhaps your company sells software as a service (SaaS), and your reps typically ask about workflows early in the conversation. From there, they can zero in on the particulars. They might ask, “What applications are your product managers using for X?” and, “How does working in Y impact your production schedules?”

O-P-C questions are the quintessential tactic that sellers can use throughout the process. They enable them to reiterate what they heard — and while it sounds simple, there’s an art to wielding these questions. Firstly, sales reps should avoid simple repetition. Instead, encourage your reps to document the buyer’s language in order to adopt their terminology. It may seem like a small difference, but it’s an efficient way to quickly build rapport.

Overall, it’s important for sales leaders to stress the organic nature of these questions. Sales reps aren’t creating scripts; they’re crafting conversations.People want to do business with people they trust, and people tend to trust people who understand their challenges.

2. How Do I Develop the Perfect List of Questions?

Research is the sales rep’s most powerful ally. While you can’t find an ideal list of questions that fit all selling scenarios, there are important points for salespeople to consider when preparing to engage prospects. The key here is to ensure that they are fully imagining the persona of the potential buyer. They should work to understand the industry, the individual’s role within the company, the metrics that person is likely measured on, and potential problems that are already on his or her radar.

After all, the probing questions that sellers would ask a chief financial officer are very different than the ones they’d prepare for a logistics manager, since they’re dealing with a different path to value in each situation. In today’s economy, where competition for capital is fierce, reps need to be prepared.

3. What if the Prospect Doesn’t Answer My Questions?

Often, when prospects withhold information, there’s a question of credibility. Sellers need to be prepared with value-based stories that resonate with their potential buyers. Drawing on previous results will help them demonstrate how they’ve provided impactful value in similar situations. If that doesn’t do the trick, it’s appropriate to politely push back. In order to reach an understanding that your solution is the best available, the salesperson and the prospect need to agree on the problems they’re trying to solve and why those problems are worth fixing.

Reps might consider saying something like, “You know, I’d love to help you, but without further insight into what goals you’re trying to accomplish, I can’t talk about solutions.” It can be a little awkward, but sometimes, that push is necessary to bring the conversation back on track.

Ultimately, you could be dealing with an issue of alignment. Priorities are constantly changing as organizations continue to adapt to the market shifts caused by the pandemic, which is why sales leaders need to work with their teams to requalify every opportunity in their pipeline. If this situation appears to be the case for your team, do yourself the favor of releasing the opportunity from your pipeline — nothing will waste time like chasing opportunities that are in “no-decision” limbo.

In times of shifting priorities, sales professionals need to partner with their potential buyers to truly deliver value. The first step to uncovering such opportunities lies in forging the authentic human-to-human connections that enable reps to uncover urgent business demands that your company is uniquely qualified to solve.

By working with teams on targeted questioning techniques, sales leaders can equip their reps to direct the value-based conversations that lead to impactful and lasting business partnerships.In times of shifting priorities, sales professionals need to partner with their potential buyers to truly deliver value.