The AE Who Converts 89% of Discovery Calls to Opportunities
One of our AEs converts 89% of his discovery meetings to opportunities. Then he wins 61% of those deals.
His secret? He challenges prospects early in discovery calls.
Here’s what that looks like: As he gets through discovery, he helps the prospect understand which other teams need to be involved to successfully test and deploy our solution. Then he challenges his contact to get them involved early.
If they won’t (or can’t), he knows he’s either talking to the wrong person or there isn’t a big enough pain to solve. He DQs the opportunity and moves on.
When they do engage the right team members, the deal accelerates. He immediately has access to all relevant stakeholders, the proof of concept is seamless to set up, and evaluation moves quickly.
This simple approach means he spends all of his time working with the right people in the right accounts. No wonder he’s always winning.
How to Challenge Prospects Early in Discovery Calls
Most AEs ask surface-level questions that sound like everyone else: “What’s your biggest challenge?” or “What tools are you using today?” These questions don’t differentiate you or test for real commitment.
The most effective discovery questions challenge prospects to think beyond their current situation and test their willingness to take action. Here are three types of questions that separate real deals from time-wasters:
Vision & Commitment Questions test for urgency and timeline:
- “Are there any deadlines tied to getting this addressed?”
- “What would your process look like if it worked well?”
- “How would you measure success in fixing this?”
Impact Amplification Questions move the conversation from problem to pain to urgency:
- “How does that affect your ability to hit [team/company goal]?”
- “Who else is impacted when this breaks down?”
Problem Discovery Questions uncover what’s broken and open the door to pain:
- “What’s the hardest part about [key process] right now?”
- “When that happens, what’s the impact on your team?”
But here’s the key: the best questions rarely move the conversation to a new topic. Instead, they open up the current conversation for the prospect to share more. The most powerful questions are often the simplest: “Can you tell me more about that?” or “I’m not sure I completely followed — can you rephrase that?”
When you prepare for discovery calls that actually convert, you’re not just planning questions — you’re planning challenges that test whether your prospect is serious about solving their problem.
Why Most AEs Are Afraid to Challenge Their Prospects
Most AEs are afraid to challenge their prospects. They’re worried about “losing the deal.”
This fear comes from buyer bias and the uncomfortable tension that exists at the start of most discovery calls. Prospects enter sales conversations with skepticism, thinking sellers are all the same, don’t listen, and will push their product regardless of fit.
When AEs feel this tension, they often retreat into safe, generic questions that don’t rock the boat. They ask about roles and priorities without any point of view. They avoid pushing back on vague answers or testing commitment levels.
The result? Discovery calls that feel good in the moment but lead nowhere. The prospect gives surface-level responses, the AE fills out their opportunity record with details, and the deal sits in pipeline for months before going dark.
The Reality: No Challenge Means No Real Deal
Here’s the thing: if your champion can’t (or won’t) engage the right people early, you don’t have a deal. You have a time-waster that’ll sit in your pipeline for months before going dark.
Every executive you talk to has fires burning across the business. And they’re choosing — consciously — which ones to let burn. All companies are full of problems, but executives only have time, money, and people to fix a select few.
The biggest mistake in discovery isn’t asking the wrong questions. It’s asking the right questions about the wrong priority. You can run a textbook-perfect discovery call and still lose the deal if you focus on the 4th or 5th biggest problem your prospect has.
When you challenge prospects early, you’re not being pushy — you’re helping them identify whether this problem rises to the level of “the” problem they need to solve, not just “a” problem they’re aware of. If they can’t engage the right stakeholders or commit to a timeline, that tells you everything you need to know about where this sits in their priority list.
This is why getting access to the right stakeholders is so critical. Without it, you’re solving problems that executives will ultimately decide to let keep burning.
What Happens When Prospects Accept Your Challenge
When prospects accept your challenge and engage the right stakeholders early, everything changes. The deal accelerates because you’re no longer working through intermediaries or waiting for information to filter up and down the organization.
You immediately have access to all relevant stakeholders who can provide technical requirements, budget parameters, and decision criteria. The proof of concept becomes seamless to set up because the people who will actually use and evaluate your solution are involved from the beginning.
Most importantly, evaluation moves quickly because you’re working with people who have the authority and urgency to make decisions. This is the foundation of the early stakeholder engagement playbook that top performers use to achieve 61% win rates.
When prospects can’t or won’t take these steps, you’ve learned something valuable: this isn’t a priority worth your time. You can DQ the opportunity and focus your energy on prospects who are serious about solving their problems.
The good news is you can learn to identify real deals from fake ones in discovery — and accelerate the real ones by challenging your prospects to take action. It starts with understanding that challenging prospects isn’t about being aggressive. It’s about being protective of your time and theirs by focusing only on problems they’re committed to solving.
