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Prioritize challenge-based discovery questions
Daily Sales Newsletter September 02, 2025 |
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Nick Cegelski: Build your discovery with hypothesis slides
Chris Bussing: Questions that prepare winning discoveries
Keith Weightman: Expand impact to strengthen urgency
Mike Gallardo: Use question flows to expose hidden gaps
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Build your discovery with hypothesis slides
Nick Cegelski explains why deals slow down when momentum fades and how to keep cycles moving in practical ways. Build high-energy, and prevent your deals from stalling:
Establish with hypothesis slide
➔ Show up to your discovery process with recent prep on a single slide.
Open with: “Here’s what I know about you and why I think you agreed to meet.
➔ Prove you did your homework, and move discovery forward quickly.
Name-drop the right people
✱ Instead of asking who else should join, recommend them directly.
Example: “I think Courtney on your team handles demand generation campaigns. She should join our demo to see how this impacts MQL scoring.”
✱ Saves your customers the effort, and potential buyer hassles
✱ Displays how you know organizational systems well enough
Pre-call before group meeting
✔ If 4–5 people will join a meeting, call each one beforehand.
Ask: “What are the main things you want to see covered?”
✔ This builds allies 1:1 so you can win group consensus faster.
Start by using “What I Heard”
⇒ Open by recapping past conversations in 2–4 bullet points.
Example: “Here’s what I heard from Val and Courtney. Michael, does that line up with how you see it?”
⇒ Proves you listened and helps stakeholders catch up in minutes.
Questions that prepare winning discoveries
Chris Bussing discusses how top-performing AEs prepare for discovery calls by asking themselves five questions before starting every meeting. Know the right questions to ask:
1. What do I already know?
Research so you can question with thoughtfulness and credibility.
➤ Review the company’s mission, values, and business model
➤ Look at revenue streams, operating costs, and 10-K risk factors
➤ Search for recent news, product launches, or funding rounds
➤ Research stakeholders on LinkedIn for additional connections
This prep helps you navigate with insights and connect professionally.
2. What questions do I ask?
Plan discovery questions that uncover what truly matters:
✔ Top business initiatives and why they actually matter
✔ Primary responsibilities and KPIs of each stakeholder
✔ Recent technology stack, and new strategic projects
✔ Costs associated with not finishing the primary goals
✔ Areas of expertise to demonstrate without outside help
Understanding gaps lets you position your solution as essential.
3. What’s my objective for this?
Understand their world and connect with how you solve problems.
❖ Prepare a 5-minute pitch tailored with a customer story
❖ Focus on business outcomes, not your product features
❖ Show relevance by framing your solution through issues
4. What’s the ideal next steps?
Go into meetings with the outcomes in mind.
↳ Secure a follow-up, like a demo or technical discovery
↳ Confirm next meetings on the spot and invite more stakeholders
↳ Ensure the next steps are meaningful, not just “let’s connect”
5. How do I want them to feel?
Sales is an emotional activity. Intentionality matters.
✱ Make your prospects feel understood, and confident in you
✱ Dress professionally and set up a background for credibility
✱ Project appropriately because emotions influence outcomes
Establish your discovery calls into well-prepared conversations.
Expand impact to strengthen urgency
Keith Weightman points out how most deals are failing because prospects choose to do nothing. Fight stagnation by asking the right questions that exposes cost of inaction:
Shift problems to outcomes
❖ Establish possible endgame scenarios if nothing changes.
“What happens if this problem doesn’t get solved?”
❖ If potential risks are described, they’re now building cases.
Expand your circle of impact
Ask: “Who else is affected by this problem?”
➤ When more people are impacted, the stronger your urgency
➤ Helps identify your stakeholders early during the process
Show respect for past attempts
Question: “What solutions have you already tried?”
✱ This portrays you really value effort beyond what’s necessary
✱ Reveals failure to avoid pitching your similar failed approach
Capture their vision of success
Ask: “What would the ideal outcome look like?”
➔ Customers words transform into a blueprint for your pitches.
➔ Reflect their definition of success, not just your assumptions.
TO-GO
Mike Gallardo: Use question flows to expose hidden gaps
Kyle Asay: Start discovery by focusing on individual victory
Brian LaManna: Must-have questions for perfect discovery
Salman Mohiuddin: Lock in time before customers get away
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QUOTE OF THE DAY
"The best discovery questions are the ones your competitors are too lazy to ask."
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