Coaching for better sales discovery questions

Better sales discovery is, perhaps, the most important selling skill. Gaining access to stakeholders and uncovering needs is key to presenting your value. 

Most discovery looks like this: What Keeps You Awake at Night?”  This approach is reactive. It makes it harder to uncover areas to add value and differentiate.

What is the value of an executive meeting if the prospect only tells you what they already know? How are you going to add value when the customer is diagnosing their own needs and prescribing their own solutions?

You are following instead of leading.

Better sales discovery should look like this: This is What Should Be Keeping You Awake at Night!”

The transition from open-ended discovery to leading with guided discovery is like a good doctor that listens to your symptoms but performs their own diagnosis.

After all, they’re the doctor and more qualified than you.

For the same reason, a doctor is more prepared to diagnose and prescribe; you are more prepared to lead the prospective buyer through discovery to diagnose the root cause of their business issues and then present solutions that are beyond their expectations.

As an example, CloseStrong is in the sales enablement business. Many times we’re talking with heads of sales who really understand their business and how it solves customer problems. What they are not experts in, and what their career has not prepared them for, is delivering high-value sales and negotiation coaching at scale. CloseStrong multiplies the effectiveness of the sales management team.

While their opinion and observations are valid and can be helpful, it is our job to walk them through a cross-functional diagnostic approach to understanding the current and desired state of their sales negotiation process and present solutions that deliver higher-quality deals, reduce discounting, improve pipeline quality, and increase forecast accuracy. 

This is accomplished through guided discovery.

So what is guided discovery, and more importantly, how does one do it? It is characterized as making the transition from asking customers what their needs are to performing a current and desired state diagnostic across all areas of their business that our solutions can impact. The steps for executing this kind of discovery are as follows:

  • Determine all levels of the customer’s business you can impact cross-functionally. We like to use three categories that align with various levels of buying influence. What are those areas that senior leaders care about that impact their strategic-level goals? Same for mid-level stakeholders owning initiatives that are in place to execute strategies, and then finally, operational stakeholders focusing on goals that enable operational aspects of executing initiatives.
  • Design specific “current/desired state” questions aligned with each area of customer strategies, initiatives, and operations that your solution has the ability to impact.
  • Execute the diagnostic cross-functionally and across geographies.
  • Prepare the current/desired state diagnostic to be presented to the customer as a value-add and gain sponsored access vs. having to earn discovery access one stakeholder at a time.
  • Find gaps between the current and desired state where your solution can bridge the gap.
  • Present your findings, ideally face-to-face in front of a group with cross-functional representation.


The good news is that when diagramming those areas of customer business you can impact, the list is finite. It also follows patterns. Mapping out business impact in great detail from strategic to operational level issues takes into consideration a very holistic impact of your value that, many times, most of your salespeople can’t identify. What we have also seen is that many sales teams are dealing with operational-level stakeholders and impact. This preparation allows them to gain access to and understand more high-level business concerns.


What emerges from cross-functional diagnostic work is nothing short of your value proposition and, in fact, many times drives incremental value the customer wasn’t expecting. The value you bring is not the long list of stuff your solution can provide but those areas where you help customers bridge gaps that help them execute strategy. Customers will fund initiatives that are tied to strategy! The additional benefit for you and the customer is that many times you uncover areas you can help with that are not on the customer’s radar and act as incremental and unexpected value.


I mentioned earlier that most organizations are not willing to grant us access (or, at the very least, it’s difficult) to execute “discovery.” However, when positioning discovery as a cross-functional, current, and desired state diagnostic, we find about 90% of the time, we have an executive sponsor us and clear the way by providing a list of key stakeholders and alerting them that this work is happening.

Again, in theory, it’s a simple transition from open-ended questions to precision-guided discovery. With a little effort, you can begin to build organizational learning and competence for one of the most important areas of selling that are in line with your buyers.

If you want to see guided discovery in action AND also receive a demo for CloseStrong, contact us today.