🚦 better discovery

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Sharpen discovery with layered questions

Jan Benedikt Mundorf outlines C-level discovery calls by following an established track helping set your meetingz, ask the right questions, while guiding next steps confidently:

1. Establish tone during first seconds

“[Name], appreciate you making time. My goal today isn’t to pitch, but understanding if we can help. If not, I’ll say so. Sound good?”

“Let’s keep it sharp. I’ll ask a few quick questions to learn more, then I’ll share what we’ve done for similar teams if it’s relevant.”

✔ This establishes mutual respect while getting permission to lead.

2. Open things with relevant contexts

Example:

“Saw you [recent change — e.g., raised Series B / hired new CFO]. What’s the biggest change ever since then?”

➔ Gets prospects talking about change, not just business operations.

3. Ask prospects with layered questions

A) Business Objectives

❖ “What are top 1–2 outcomes you’re responsible for this quarter?”

❖ “What’s currently in the way of you from making this decision?”

B) Process + Painpoint

✱ “Walk me through your current [X] processes.”

✱ “What’s broken or inefficient happening now?”

✱ “What are costs associated of not solving this?”

C) Strategic Outcomes

➤ “How visible is this problem across your board?”

➤ Slow down when talking. Use pauses and silence.

4. Build revelant mid-call summaries

“So, you’re spending [X] hours/week on [pain], it’s affecting [team], and there’s pressure to fix it by [timeline]. Is that accurate?”

↳ Confirms your understanding while providing solution alignment.

5. Guide prospects next step instantly

“Sounds like a fit based on what we’ve seen with [similar customer]. I’d suggest:

1. Bring in [decision maker, stakeholders]

2. Walking through customized solution

3. Aligning towards your business cases

   
   “Does early next week work?”

4. Direct, specific, and outcome-driven

6. End with a confident close

“Thanks for your honesty. I’ll follow up with a quick recap of the call + proposed next steps. Anything you’d like to add before ending this call?”

✔ Leaves no room for ambiguity behind.

Better customers data procurement

Andy Whyte and Pim Roelofsen breaks down three proven discovery questions making salespeople feel almost certainly leveraged during sales conversations with prospects:

1. Look backward, not forward

Instead of asking on “decision process,” ask:

“What happened the last time you bought a solution like this?”

➤ Prospects recall actual steps, not just future guessing

➤ Reveal hidden blockers: legal reviews, multiple checks

➤ If they’ve never bought, extra coaching will be needed

2. Anchoring with benchmark

Prospects often avoid giving metrics.

To unlock, frame with proven number:

“With companies like yours, churn is around 20%. How does success look like for you?”

❖ Gives prospects something concrete to respond on

❖ Builds credibility: “others have shared this with me”

❖ Open space for numbers instead of vague answers

3. Trigger decisions naturally

Near the end of a meeting, try asking questions:

“It sounds like you have few next steps in mind.”

✱ Feels like actual recognition, instead of sales-driven trap

✱ Prospects often respond with actions, people, timelines

✱ Works globally through consistently effective disarming

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Connect discovery pain to business impact

Celeste Berke Knisely discusses how the first discovery call question possibly make or break your ability to sell in business levels. Look for problems using the right questions:

1. Asking “by design,” not “by default”

If potential buyer says, “We want our team to be more efficient,” respond with:

➔ “When you say more efficient, what does that really mean?” (pause)

➔ Link process challenges to business problems: weak quota attainment

↳ Once they confirmed, you’re now aligned to problems leadership cares for.

2. Buyer says, “I want better reporting.”

❖ “What’s currently driving your need for better reporting strategy now?”

❖ Connect answer to missed revenue targets, poor forecasting accuracy.

3. Prospect looks for smooth processes

➤ “What is the current impact of slow onboarding on revenue or customer retention?”

➤ Link delayed time-to-productivity, or missed deals from poor experiences.

4. Customer search better automations

✔ “If you had automations today, what measurable business outcome improves first?”

✔ Push toward cost savings, quicker deal cycles, or increased deal volume per rep.

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