One of the biggest obstacles to uncovering MEDDIC is one's ability to conduct discovery. Before I go into how you can ask better questions and drill deeper into your prospects pain, I want to make something very clear:
Discovery is not a one time event, discovery is a continually iterative process throughout the sales cycle.
Now that we are clear on that, let's go over some tips on how you can drill down and ask better questions.
Start with Open-Ended Questions
Instead of asking yes/no or leading questions, you should begin with open-ended questions that encourage prospects to share their challenges in detail. These questions help uncover broader problems and insights. Examples include:
“Can you walk me through your current process for [specific task]?”
“What’s the biggest challenge your team is facing with your current solution?”
“How is this issue impacting your day-to-day operations?”
Use Follow-Up Probing Questions
After an initial response, you should dig deeper by asking follow-up questions to clarify and gain more insight into the pain points. This shows the prospect that the rep is truly listening and wants to understand at a granular level. Often times we accept their initial answer without probing. Here are some examples of follow-up probing questions:
“You mentioned [specific issue]. Can you tell me more about how that’s affecting your team?”
“How does that problem impact other areas of your business?”
“Why do you think this issue has persisted, and what has been your approach to solving it?”
Focus on the “Why” Behind the Problem
Asking “why” helps uncover the underlying causes of challenges, revealing the root pain points that can be addressed. Some good ways to phrase these questions include:
“Why do you think this issue is happening now?”
“Why has this problem become a priority for your team at this point?”
“What’s stopping your current solution from addressing this challenge?”
Ask About Consequences and Impacts
Understanding the consequences of the problem helps the you grasp the full scope of the prospect’s pain and can lead you to develop strong Metrics. Questions focused on business and personal impact can help:
“How is this challenge affecting your overall business goals?”
“What are the financial or operational impacts of not solving this problem?”
“How does this issue affect you personally in your role?”
Frame Questions Around Value and Priorities
Understanding what the prospect values most and what their priorities are can help you position their solution effectively. Examples include:
“What would a perfect solution look like for your team?”
“If you could solve this challenge, what would the impact be on your team or department?”
“What’s the most important outcome for you in choosing a new solution?”
Use Hypothetical Scenarios to Gauge Perspective
Presenting hypothetical situations can help prospects think critically about the challenges they face, often leading to deeper insights. These type of questions also help maintain a sense of urgency in solving the problem. Questions like these help:
“If this issue were resolved, how would it change the way your team works?”
“What would happen if you didn’t address this issue in the next 6 months?”
“How would your ideal solution integrate with the other systems you’re using?”
Be Empathetic and Human
Empathy is key in building trust. Asking questions in a way that shows genuine concern for the prospect’s situation helps them open up. Examples of empathetic questions include:
“It sounds like this has been a frustrating process for your team. How have you been managing that so far?”
“That sounds like a challenging situation. How have you tried to address it in the past?”
Uncover Decision-Making Criteria
Toward the end of the discovery process, you should ask about the criteria and process for making decisions. This helps tie pain points to the decision-making process:
“What factors are most important to you when evaluating new solutions?”
“Who will be involved in the decision-making process, and what are their priorities?”
By blending these types of questions into the discovery phase, you can uncover deeper insights, build stronger relationships, and ultimately offer a solution that’s genuinely aligned with the prospect’s needs. The goal is to shift from a transaction-focused conversation to a problem-solving dialogue.
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