🎙️ discovery made simple

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Crush discovery with these 12 questions

Mike Gallardo reveals 12 discovery questions AEs use to guide better conversations.

Ask questions that show curiosity, context, and control.

Center on their priorities

💬 “Let’s start with what brought you to us today. What are you looking to accomplish?”

This opens the call with their goals, not your agenda.

Map their friction points

💬 “Can you put me in your shoes and walk me through your process step by step?”

Uncover the workflow gaps your solution can address.

Understand their world

💬 “Most founders I speak with have priorities like [X]. Is that true for you, or is something else top of mind?”

Position yourself as a peer, not just a desperate vendor.

Confirm sales alignment

💬 “Looks like we’re in a great position to help. Do you mind if I recommend next steps?”

Ensure your customer’s buy-in before moving forward.

Clarify what matters most

💬 “It really stood out when you said [X] — can you share more about that?”

Show you’re listening closely and value what they say.

Summarize often:

💬 “Here’s what I’m hearing so far… did I get everything correct?”

Prevent misalignment and reassure you understand their needs.

When you’re demoing:

• “What stood out to you about what we just walked through?”

• “Who else on your team would benefit from this feature?”

• “What was running through your mind as I showed that?”

For next-stage alignment:

↳ “Would you be open to connecting on Slack for quick communication?”

↳ “What steps would need to happen to make a confident yes or no decision?”

↳ “If both parties align on pricing, would we be your first vendor of choice?”

Each question builds momentum and trust without forcing the sale.

Free resource 🎁 

Transform discovery calls into your best rebuttal

Ray Green explains why most deals are being won early in the discovery stages.

A strong discovery builds the foundation for an easy deal close.

Discovery is your genuine close

✔ Uncover motivation, and the buying process itself.

✔ When discovery is targeted, closing feels natural.

“How many users?” “What servers?”

✔ If it’s weak, objections start piling up at the end:

Engineer discovery around the close

Every question you’re asking should serve closing your deals.

✔ Identify pain and define gaps between today and tomorrow

✔ Clarify urgency: “Why are we talking now and not six months ago?”

✔ Map the buying process: “Who’s usually involved in decisions?”

✔ Expose price sensitivity beforehand during sales conversations

Ask questions about what you’ll need later - your case for change.

Use their words as your close

✔ When a buyer says, “We’re not ready,” point back to what they said earlier.

Example:

“You mentioned your current provider’s slow response time caused a client issue and missed deadlines. Are those no longer a priority?”

✔ Your best rebuttal isn’t a script - it’s what they’ve mentioned in discovery.

Handle objections before they surface

Waiting until the proposal stage to uncover objections is too late.

At that point, decisions are often made, and defenses remain high.

✔ Discovery is the cheapest time to address objections because:

➤ Buyers are more willingly open

➤ You’re still controlling the pace

➤ Money talk triggers resistance

✔ Document your top five objections. Rewrite them as discovery questions:

• “What are you currently investing in IT services?”

• “Who else is involved when you evaluate vendors?”

• “If we find the right investment, is that possible?”

Recap to reinforce alignment

✔ At the end of discovery, summarize what you’ve heard:

“Here’s what your challenges are, why they matter, what success looks like, and who’s involved.”

✔ Check for mutual agreement and show you’ve listened.

Sell with math, not charm

Meredith Chandler tells the story of a rep earning $750K annually.

It wasn’t because of charm, friendliness, or rapport. It was because he only asked quantifiable questions.

This post breaks down exactly how he did it and how you can apply the same approach to your own discovery process.

Ask about time first

Start by quantifying effort:

➤ “How long does it take you to [do X]?”

Example: “How long does it take to calculate commissions each quarter?”

Buyer: “About 30 hours.”

That’s your wedge. Now start stacking.

Break the problem into costs

Use simple math to expose hidden pain.

✔ Time cost: “So that’s 4 full workdays. What’s your time worth? Or, what could you have done instead?”

✔ Error cost: “How often do mistakes happen? Have you ever overpaid?”

✔ Ripple effect: “What happens when reps don’t trust their comp?”

When they say reps re-run numbers, ask:

→ “What does that cost in time or output?”

→ “Has anyone ever left because of comp issues?”

Keep going until you uncover all the downstream impacts.

Go deeper to uncover business impact

Don’t settle for surface-level data—push further:

➤ “What’s your hiring cycle cost when someone leaves?”

➤ “Recruiter fees? Ramp time? Missed quota?”

Buyers will start to stack their own numbers. That’s when the conversation shifts from problem → business case.

Make the math undeniable

Once you’ve gathered all the inputs, recap the totals clearly:

✔ “30 hours + $20K in errors + $5K in lost productivity + $20K recruiter fee + $200K in missed ramp = $240K/year. Do I have that right?”

Now you’re no longer solving a spreadsheet problem.

You’re solving a $240K business problem.

Key mindset shift

✘ Don’t focus on feelings
✔ Focus on financial impact

Small talk and charisma won’t drive urgency.

Math will.

Recommended tools*

• Mailshake: Cold email made simple and effective

• Smartlead: Automate outreach without losing the human touch

• La Growth Machine: Multichannel prospecting that actually scales

• Systeme.io: All-in-one platform to launch and sell your products

Check them out!

P.S. Stay tuned for tomorrow’s issue that breaks down what great demos do differently.