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🗝️ demo ≠ pitch
Use these questions to make buyers talk
Daily Sales Newsletter October 01, 2025 |
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In today’s issue:
Mor Assouline: Prospect alignment before moving forward
Zac Rattcliffe: Why sales pitches need an upfront contract
Mike Gallardo: Strategize your demos with buyer workflows
Max Lupertz: Make your demos feel valuable, not instructive
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Prospect alignment before moving forward
Mor Assouline breaks down why micro-closing defeats vague demo questions.
Keep your customers aligned by confirming value before moving forward.
Ask alignment questions
➔ Confirms your solution matches expectations before moving forward.
↳ “Do you feel this is aligned with what you’re looking for?”
Alignment questions ensure you’re building on the right foundation.
Gauge satisfaction directly
➔ Highlight gaps early so you can address them immediately.
↳ “On a scale of 1–10, where do you feel this sits?”
Satisfaction establishes how well the prospect sees your fit.
Connect features to pain
➔ Keep your conversations anchored in their words, not yours.
↳ “Is this what you had in mind when you said you needed to [solve pain]?”
↳ “Does this feature address the challenge you mentioned earlier?”
Linking features back to pain points shows direct relevance.
Involve decision-makers
➔ Promote multi-threading and prevent surprises later.
↳ “Will [other stakeholder] think this solves [problem]?”
Involving stakeholders reduces risk and accelerates buy-in.
Test their confidence
➔ Surfaces hidden doubts early so you can address them.
↳ “Based on [your problem], how confident do you feel this will solve it?”
Confidence uncovers objections before they stall deals.
Fitting into strategy
➔ Forces prospects to see how your solution aligns with their priorities.
↳ “Would this approach fit within your current strategy?”
Strategic fit proves your solution isn’t just tactical - it’s essential.
Why sales pitches need an upfront contract
Zac Ratcliffe outlines a 7-step pitch framework that keeps customers engaged, builds authority, and leads to more closed deals.
Structure your pitch like a movie - build momentum towards your close.
1. Upfront contract
🔑 Establish how the meeting will run, and when you’ll ask questions.
💬 Example: “Here’s how we’ll use our time: I’ll ask a few questions to understand your situation, then walk you through how we help companies like yours, and if it makes sense, we can cover next steps at the end. Does that sound good?”
Rules keep you in control and drop the buyer’s defensive guard.
2. Fact-finding
🔑 Investigate problems and their position during operations.
💬 Example: “How long has this issue been costing you time and money? What happens if it’s not solved in the next 6 months?”
You can’t provide solutions if you don’t understand their problem.
3. Story and big idea
🔑 Share the origin story behind your solution.
💬 Example: “We struggled with the same bottlenecks you’re facing. That’s why we created a solution that cut our process time in half and helped clients free up 20 hours per week.”
Clients buy proven outcomes, not raw data.
4. Create intrigue
🔑 Back up your stories with credibility and testimonials.
💬 Example: “One of our clients in your industry was losing $50K a quarter due to delays. After using our system, they cut that loss in half within 90 days.”
Make them want your solution before they even see it.
5. Product breakdown
🔑 Now reveal the offer - features connected to their problems.
💬 Example: “You mentioned manual reporting takes 10 hours a week. Let me show you how our dashboard automates that in under 10 minutes.”
Personalization makes your demo memorable and relevant.
6. Value proposition
🔑 Bridge problem cost and solution price. Anchor outcomes, not your pricing.
💬 Example: “Right now, this inefficiency costs your team about $100K annually. Our platform is $25K a year, which means it pays for itself four times over.”
When value is established, price becomes irrelevant.
7. Closing deals
🔑 Use language that invites a “no” to avoid fake yeses.
💬 Example: “Would you be opposed to moving forward today if everything we discussed feels like the right fit?”
Closing becomes easy when steps have momentum.
Visual of the week:

Match demos to buyer workflows
Mike Gallardo shows how to ask stronger questions that get to the truth.
Use stronger questions that tie your product directly to the buyer’s situation.
“What was running through your mind as I was sharing that?”
📌 Use this right after showing them a feature to capture live reactions.
This surfaces unspoken thoughts before they turn into objections.
“Before I show you how to X, can you walk me through your process step-by-step?”
📌 Ask this before showing features to compare your solution with their workflows.
Their detailed process gives you the language for framing your product demos.
“When you need to X, what happens?”
📌 Helps you learn their exact movements for core workflows.
This reveals inefficiencies you can offer direct solutions to.
“Who else on your team would benefit from being able to X?”
📌 A natural way to multithread and involve other stakeholders.
Strong demos plant seeds for broader team adoption scope.
“If a new solution was live tomorrow, what’s the first thing you’d want to try?”
📌 Reveals the product features they value most.
Use their priority as the anchor for your pitch.
“Walk me through the last time you had to [process]. What steps did you take?”
📌 Provides you with detailed, real-world examples.
Stories convey pain better than high-level talk.
“What would you say is the most time-consuming part of that process today?”
📌 Surfaces the bottleneck you should emphasize.
Highlighting time drains makes your ROI clearer.
“When are you hoping to have a solution in place?”
📌 Simple but effective way to align on timelines.
Knowing urgency helps you pace deals correctly.
TO-GO
Krysten Conner: Close your deals using the STAR method
Chris Orlob: Discounts are weaker than lost sales revenues
Max Lupertz: Make your demos feel valuable, not instructive
Gabe Lullo: Potential demo mistake that signals carelessness
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QUOTE OF THE DAY
"Make the presentation 100% in terms of the customer’s needs. Engage with questions and promote dialogue."
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