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Keys to Conducting Deep & Effective Sales Discovery

By: Teresa Weirich

August 2, 2018

When a prospective customer agrees to spend an hour (or more) of their time to divulge their challenges, opportunities, and goals through a discovery process with a sales professional, they are taking a big risk. The discovery call(s) is truly the foundation of the entire sales process (which is why we built this awesome discovery call template) and, if run effectively, can create a trust and a mutually beneficial bond that will last through the entire sales process. If not run effectively, though, the consequences to the deal can be severe: the prospect may not establish the trust that it requires to move forward, important details may be left out, and pertinent questions may go unanswered that will later cause the entire deal to fall apart.

Whether a sales professional has a year of experience or two decades of sales acumen under her belt, learning how to conduct deep and effective discovery can set her apart from the entire competitive field. Fortunately, conducting mutually beneficial discovery sessions isn’t rocket science and in fact, most sales teams already have playbooks in place that are intended to guide them through the discovery process. But what happens if they miss a question (or more)? What if the prospect refuses to answer? What if the call is cut short and the sales professional isn’t able to get all that she needs in one call?

The way that sales reps handle discovery calls says a lot about their sales processes. Afterall, the discovery call(s) either sets up the entire sales process for success or for immediate or eventual failure. In this article, we’ll take a look at 4 tactical ways that sales leaders can ensure that team members always have the best discovery calls possible.

1. Determine the NEED to know questions versus the GOOD to know

Just like when sales development reps have to have an answer to certain questions in order to qualify a lead, sales professionals should have a predetermined set of questions that absolutely need to be answered before the discovery process is marked complete. These questions should relate to categories like:

  • Buying process
  • Budget
  • Compelling event
  • Influencers or supporting teams
  • Vendor assessment process and risk management
  • Current vs future workflows
  • And so on

When it comes to creating a discovery call playbook, every prospective customer is different and therefore some of the questions should differ as well—after all, no two prospective customers are the same and they shouldn’t be treated as such. However, every sales leader should have a framework in place to make sure that the most critical questions are always answered. Sometimes, when a call is running short or a prospect isn’t sharing in-depth information, it can be tempting to table questions for another time. That’s fine, so long as the questions are guaranteed to get answered at some point. But unfortunately, those questions are often forgotten about until it’s too late. That’s why it’s key to differentiate the need-to-know discovery questions from the nice-to-haves.

2. Personalize the discovery call process for the prospective customer

In our People > Processes series, we’ve heard from many sales professionals that the key to effective discovery calls is to research, research, research. Courtney Shaffer, Global Strategic Account Manager at Emarsys, shared that she does in-depth research before every single discovery call. For instance, she might dig into a topic by using this positioning: “I previously read in the annual report that your company has been experiencing this particular pain point, but what does that mean for you and your team?” She also seeks to clarify any confusion by using a soft approach: “In my definition, I see this particular challenge this way, but talk to me about how you see it. What is your agent of change? What will take your business where it needs to go?”

By asking personalized, open-ended questions that get to the heart of the matter, Courtney is able to navigate potential pitfalls that could derail the deal later on.

3. Ask the same questions in different ways—and then listen

Most sales reps have experienced a prospective customer that won’t answer key discovery questions. While they may not think those unanswered questions will hurt the deal, it’s unlikely that the end solution will be as helpful to them as it could be. One of the best skills that sales professionals can learn is to ask questions in different ways. For instance, if a prospect doesn’t want to share how the budget approval process works within their organization, then it’s key to find a different way to ask the same question (perhaps later on in the conversation). Rather than repeating the same exact question, the rep may ask: “Can you share with me how your organization determines if or when to adopt a new product or solution? What’s the process look like from your point of view?” By asking the same question with a different context, the sales rep can get to the heart of the issue while also maintaining the relationship.

Building on our prior example, Courtney will ask several thought-provoking questions and then she’ll sit back and let the prospect talk. Rather than jump in and add her two cents, she simply listens—for keywords, pain points, emotion, and any key points that she can use to articulate the problem (and solution) back to her prospects in future conversations. One of the most challenging aspects of the discovery process can be letting the prospect take the lead while also effectively guiding the conversation down the right path.

4. Balance flexibility and consistency in discovery calls

As we’ve explored in a previous article on Openview Ventures, sales processes should strike a balance between flexibility and consistency—and this is especially true during the discovery call. If the sales professional is too flexible in the way that they manage their discovery processes, then chances are greater that they’ll miss a key question, phrase an important message incorrectly, or move on if the prospect doesn’t answer a question. But too much of a rigid process means that the sales rep may risk sounding robotic, impersonal, and out of touch with the prospective customer’s challenges, opportunities, and goals. Sales leaders must determine what the right balance of flexibility and consistency is when it comes to conducting deep and effective discovery. For regulatory-driven industries, consistency may be the driver. But for martech companies on the other hand, sales leaders may lean more towards the flexible end of the spectrum.

Guiding Sales Professionals Through Discovery

The best sales professionals guide prospective customers through discovery calls in a way that is natural and beneficial for both parties—not just the sales rep. But staying on message and making sure to ask all of the right questions can be a lot to handle when the main point of the call is to listen and capture what the prospect is saying.

Costello’s sales playbook software allows sales reps to stay present in the conversation and guide themselves through the discovery process by asking the right questions so they can stay engaged and tuned in to the conversation at hand. And if they miss a question or don’t get the in-depth response that’s needed? The question re-assigns itself in the call template so the need-to-know questions are never missed.


  • Teresa Weirich's Headshot
    Teresa Weirich

Ready to Learn More?

For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.

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