❓ probing questions

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Going deeper than surface-level questions

Nate Nasralla provides discovery questions that go beyond surface-level needs and uncover what really achieves complex deals by opening doors to expansion momentum:

Asking the unexpected

📌 Open by framing past wins, then push them to think beyond it.

“Obviously, [main product benefit] is the goal. But if your biggest win came in a totally different area, where would that show up?”

📌 Get prospects thinking beyond initial use case into expansion.

Dig into past failures

❖ Invite prospects to reflect on when things didn’t go as planned.

“Walk me through times when your team invested in something that worked technically but didn’t deliver the outcome. What happened?”

❖ Reveals how they define success, internal politics, and metrics.

Check resources early

💡 Highlight cross-team effort required to make projects succeed.

“If this gets approved, what’s one resource you’ll need to ‘borrow’ from another team? How comfortable are you having that conversation?”

💡 Flag in advance delivery roadblocks that might stall adoption.

Reveal exec concerns

➤ Positions the questions around heavy leadership pressures.

“When you show this to [exec sponsor], what’s one question they might ask that you hope they don’t? And what would your honest answer be?”

➤ Surfaces hidden doubts about potential executive buy-in.

Define timeline success

✅ Frame it as looking beyond accountability moments.

“Six months from now in a QBR, if someone asks, ‘Was this worth it?’ what would you show on screen? What would make you nervous to show?”

✅ Clarifies how success will be measured and tracked.

Testing for deal urgency

✱ Use this to gauge how much the project actually matters.

“What’s your Plan B if this doesn’t get approved?”

✱ If there’s no alternative, the project might not be a priority.

Reframing problems with CEO inbox questions

Steve Victor breaks down how to ask discovery questions that feel natural instead of salesy by moving prospects from surface-level issues to actual business problems:

➤ Ask why they took the call

💬 Most prospects don’t take every meeting.

💬 Asking why twice reveals actual trigger:

• If they mention a lead source → question them why again

• If they describe a situation → give multiple-choice options

• If they state what they want → invert given feature-benefits

💬 This uncovers motivation, not just polite surface answers.

➤ Use “moment” questions

➔ Shift from operational pain to executive problems.

“You probably didn’t wake up worried about renewal tracking. When did this become a problem - renewing unneeded software, over-buying licenses, or just a gut feeling?”

➔ These questions direct conversation from annoying to strategic.

➤ Trigger business impact

🎤 Connect executive problems with bigger outcomes.

“You mentioned reducing software spend from $1.5M to $1M. Would fixing renewals hit that, or is there a bigger play?”

🎤 Push-pull questions reveal whether problems are worth solving now.

➤ Imply selective response

✱ Guide prospects to pinpoint issues without pressure.

“When someone’s worried about vendor spreadsheets, it’s usually renewals or new spend. Which is it here?”

✱ Multiple-choice framing narrows their actual problems down.

➤ Impact reflection values

👉 Quantify problems by projecting into the future.

“If nothing changes in 6-12 months, does this stay the same, get worse, or become a bigger headache?”

👉 Reflection questions turn vague pain into backed urgency.

➤ Champion’s perspective

↳ Learn to know your allies and blockers early in the game.

“If you fixed this, who would be most excited? Who might push back?”

↳ Identifying your champions and resistance helps map the battlefield.

➤ Executive inbox quarters

✔ Elevate your problem to authorities with power.

Example: “If your CEO saw an email about this, what would the subject line say?”

✔ Framing problems at higher levels connects directly to high-level priorities.

Turn new features into actual solutions

Salman Mohiuddin tackles reasons why one AE consistently ranks among the high-performers globally: it’s not flashy strategic moves, but execution on fundamentals:

Fixate on the problem

⇒ He doesn’t lead with product features.

⇒ He maps the business problems deeply:

✅ What it solves for prospects

✅ How it impacts each persona

✅ How teams are handling issues

✅ What happens if they ignore it

✅ Which metrics are getting hit

⇒ So when features launch, he’s already asking:

Seller: “What real-world problem does this help solve?”

Prospects think: “He actually understands my world.”

Treat discovery as ongoing

He can outline every live deal with precision:

• The problem and what’s causing it

• The negative impact across the org

• Who’s affected and why it matters

• How it connects with exec priorities

• Risks that could be stalling the deal

• Who decides the next steps forward

Examples of how this presents realistically:

🔑 Prospect: “We’re already using workarounds.”

AE: “What’s the risk if the workaround breaks during a critical time?”

🔑 Prospect: “This is more of an IT-based problem.”

AE: “Got it. Beyond IT, who else feels the impact every day?”

🔑 Prospect: “Budget’s kind of tight this quarter.”

AE: “If this stalls, which executive priority gets pushed back?”

Activate with internal teams

He consistently equips people to add value:

➤ Prepares SEs before every call is taken

➤ Sends execs a 1-pager before meetings

➤ Brings leadership into alignment calls

➤ Creates mutual plans for both parties

➤ Partners strategically so everyone wins

Examples of how he does this:

📌 To an SE: “Here’s the client’s problem in their own words. Can you demo specifically how this particular feature fixes their challenge?”

📌 To an exec: “You’ll be meeting their COO. The biggest concern is risk during rollout. Could you address how we’ve handled this for similar accounts?”

📌 To a partner: “If we win this together, here’s the piece you’ll be leading on. What would make this deal equally valuable for you?”

These strategies are what keep him consistently at the top.

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