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AI can tell you almost everything about a prospect in 30 seconds.
Their annual report.
Their recent news.
Their industry pressures.
Their competitors.
Their likely initiatives.
Their probable challenges.
Yet despite having more information than ever before, many discovery conversations are becoming less meaningful.
Why?
Because information is not curiosity.
That observation became the focus of a series of conversations between us about discovery, customer engagement, AI, and what separates average sellers from exceptional ones.
One discussion in particular centered on the TEDW framework, a simple yet powerful approach to structuring open-ended questions. Ryan introduced the framework during one of our conversations, and it immediately resonated because it provides a practical way to apply one of the most important elements of discovery: genuine curiosity.
Those discussions ultimately led to a shared conclusion:
As AI makes information easier to obtain, curiosity becomes more valuable.
What follows is our perspective on why curiosity is becoming one of the most important skills in modern selling and why it remains fundamentally human.
The Real Discovery Problem
Most sellers do not struggle with discovery because they lack a methodology.
Frameworks and methodologies such as MEDDPICC, Command of the Message, Great Demo!, and Peter E. Cohan’s Doing Discovery provide valuable structure and proven approaches for customer conversations. They help sellers understand what information matters and provide a structured way to capture relevant insights.
Yet no methodology can make you genuinely curious about another person’s business problem.
That is the real gap.
Discovery is not about asking a list of questions.
It is about understanding what matters most to the customer, why it matters now, what happens if nothing changes, and who is affected.
Done well, discovery uncovers the customer’s Critical Business Issue: the problem or opportunity important enough to drive action.
When we understand the Critical Business Issue, everything else becomes easier. We can align conversations to outcomes, demonstrate relevant capabilities, and build a business case that matters to the customer. Yet when done poorly, discovery often devolves into a polite interrogation followed by a generic demo.
And we all know how that ends.
The seller presents.
The customer nods.
The opportunity stalls.
Everyone pretends to be surprised.
Curiosity Is the Differentiator
If discovery is so important, why do so many teams struggle with it?
Many organizations have a discovery methodology. Far fewer have built a culture of curiosity around it.
The best discovery practitioners, whether in sales, consulting, medicine, law enforcement, or investigative journalism, share a common characteristic:
Genuine curiosity.
They are not simply trying to get through a list of questions. They are trying to understand.
That distinction changes everything.
Curious people ask better questions. They listen differently. They follow threads instead of agendas. They stay engaged when the conversation takes an unexpected turn.
Most importantly, they continue digging long after others believe they have enough information.
That is often where the most valuable insights emerge.
And the payoff extends beyond any single deal.
Curiosity doesn’t just make you a better seller. It makes you a better learner, a better teammate, and a more interesting person.
Dale Carnegie said it best:
“To be interesting, be interested.”
A Simple Framework for Curiosity
Originally popularized by Nikki Anderson in user research and qualitative interviewing, TEDW provides a simple way to structure open-ended questions that encourage customers to tell their story in their own words.
TEDW stands for:
- Tell me about…
- Explain for me…
- Describe for me…
- Walk me through…
The authors also suggest one additional prompt: “I’m curious about…” We’ll use it later.
Instead of asking:
“Is your current process inefficient?”
Try:
“Walk me through your current process.”
Instead of asking:
“Are reporting delays causing problems?”
Try:
“Tell me about how reporting works today.”
Instead of asking:
“Would faster access to data help?”
Try:
“Describe what happens when your team cannot get the data they need.”
The first version points the customer toward your answer.
The second version creates space for their answer.
That is where discovery begins.
Yet open-ended questions are not the destination. They are the starting point. Their purpose is to create opportunities for expansion.
In fact, there are three types of discovery questions most sellers are familiar with, yet most only use two of them.
Open questions create space and invite the customer to tell their story. That is what TEDW delivers.
Closed questions confirm understanding and create forward motion, though used too early they shut the conversation down.
Between them sit expansion questions, sometimes called investigative or layering questions, which help us explore what the customer just said.
That middle layer is where curiosity lives, and it is the one many sellers skip.
The Power of Expansion
One of the most valuable concepts in Peter E. Cohan’s Doing Discovery is the use of expansion questions.
Most customers begin with symptoms.
“Our reports take too long.”
“The process is manual.”
“The team is frustrated.”
Those statements are useful, yet they rarely reveal the Critical Business Issue.
Expansion questions help us move beyond symptoms to understand consequences, business impact, urgency, and value.
A seller can ask:
“Walk me through your process.”
Customer:
“Our managers spend hours every week reconciling numbers manually.”
Many sellers stop there and immediately pivot to a presentation.
“Got it. Let me show you our dashboard.”
That is what we call Premature Elaboration Syndrome: jumping to a product pitch before you’ve understood the problem well enough to make it relevant.
Curiosity leads us somewhere different.
“I’m curious, how often does that happen?”
“Tell me who else is impacted by this.”
“What does that cost the business?”
“Explain what happens if the problem continues.”
“Walk me through why it has become important now.”
Notice the transition.
“I’m curious about…” is how you go deeper without it feeling like an interrogation.
“I’m curious about the data access piece you mentioned. Can you tell me more about how that’s managed today?”
It signals genuine interest, not a pivot to pitch.
Those questions help uncover the Critical Business Issue: the reason the customer is willing to spend time, money, and political capital pursuing change.
Discovery finds the problem. Curiosity finds the weight of it.
Where Does AI Fit In?
AI isn’t leading conversations or building trust with your clients.
It doesn’t know which thread to pull in real time. It hasn’t heard the hesitation in a customer’s voice, noticed what they didn’t say, or understood the human implications behind a seemingly simple answer.
That gap is the whole point of this article.
Use AI before the conversation, not during it.
AI is exceptional at helping you understand a company’s business model, recent news, likely pain points by industry, and the personas you’ll be meeting. Do that work in advance so you walk in informed.
But the moment you’re in the room, or on the call, put it down.
The customer doesn’t need you to recite what their 10-K said.
They need you to be present.
AI gives you the foundation to become curious faster. It doesn’t replace curiosity itself.
The sellers who will win in an AI world aren’t the ones who automate discovery. They’re the ones who use AI to show up prepared enough that they can spend the whole conversation being curious and actually listening.
How Do We Get Better?
Curiosity improves the same way any meaningful skill improves: through deliberate practice, honest feedback, and repetition over time.
- Practice with specific role plays
Start with role play, but make it specific. We like to call the exercise “Have You Met TED?” The reference is intentional, and the format is simple:
- Set a realistic customer scenario.
- Pair people up.
- Have one person play the customer while the other practices turning closed questions into open and layered questions.
The goal is not to perform perfectly. The goal is to notice where you stop digging and why. Make it a habit, not a one-time exercise.
- Use AI as a practice partner
AI can do more than research accounts. It can help sellers practice. Run a discovery scenario, ask AI to play a skeptical economic buyer, and then debrief where you led the witness instead of following the customer’s thread.
The feedback is immediate, and there is no ego in the room.
- Review calls for missed opportunities
Record discovery calls and listen back, but do not listen only for what you said. Listen for what you did not ask:
- The follow-up question you skipped.
- The thread you dropped.
- The moment you pivoted to pitch because the silence felt uncomfortable.
That is where the real coaching lives.
- Invest in discovery as a craft
For teams that want to go deeper, the Doing Discovery Workshop led by the Great Demo! team is built on a seven-level repeatable methodology designed for exactly this purpose.
The sellers and SEs who treat discovery as a craft, not a checkbox, are the ones who compound over time.
Coaching for Curiosity: A Leader’s Role
Leaders can teach questioning techniques quickly. Coaching genuine curiosity takes longer. It requires a more deliberate, systematic approach.
The guidance above applies to individual practitioners. For leaders, the challenge is helping others build the habit of curiosity and use it consistently in customer conversations.
- Make it safe not to know
If your team feels pressure to have the answer in every customer conversation, they will stop asking questions and start presenting.
Create room for responses such as, “I don’t know. Tell me more.” Treat that as a sign of discipline, not weakness.
- Debrief the questions, not just the outcome
After a discovery call, do not stop at, “What did we learn?” That question matters, but it is not enough.
Ask questions that reveal how the conversation developed:
- What question opened the conversation up?
- Where did we stop digging too early?
- What thread should we have followed further?
That is where the real coaching lives.
- Model curiosity in the moment
If you are on a call and something genuinely interests you, ask about it. Let your team see you follow the customer’s thread instead of forcing the conversation back to your own agenda.
Over time, that example teaches more than any coaching framework. It shows that curiosity is not a technique. It is a leadership behavior.
Curiosity Compounds
Customer-facing team members and leaders who commit to curiosity don’t just close more deals.
They build sharper instincts, stronger relationships, and careers that hold up over time.
It’s also the hardest thing to teach, which means the people who develop it deliberately have a real and durable edge.
That’s the whole point of discovery.
Not to extract information.
To genuinely understand someone well enough to help them.
Be curious. Everything else follows.
About the Authors
Paul H. Pearce is President of Great Demo! LLC. He works with sales and presales organizations to improve discovery, customer engagement, and demonstrations that align to business outcomes.
Ryan Garrett is a technical sales leader known for his thoughtful approach to customer discovery, coaching, organizational learning, and the practical application of AI. He is passionate about helping teams improve customer engagement through curiosity, effective questioning, and continuous learning.
A Note from Paul
One of the unexpected benefits of teaching, coaching, and working with sales teams is the opportunity to learn from others.
Ryan’s willingness to challenge assumptions, connect ideas across disciplines, and focus on understanding what truly matters to customers was a significant influence on this article. Our conversations about curiosity, discovery, and AI pushed my own thinking and ultimately helped shape many of the ideas presented here.
If the ideas discussed in this article resonate with you, I encourage you to connect with Ryan on LinkedIn and continue the conversation with either of us. I believe you’ll find him to be as thoughtful, insightful, and generous with his ideas as I have.