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Questions making trial runs into closed deals

Marcus Chan discusses how majority of sales trials fail because reps make them like demos instead of risk minimizing exercises. Eliminate weak opportunities and lock in:

1. "What happens if you don't solve this instantly?"

➔ Search for measurable pain like “47% lower productivity.”

➔ Vague answers= no sense of urgency = missing deals

2. "Have you solved this with your current vendor?"

❖ If not, 90% of CFOs will usually send them back

❖ Document why current tools fail before starting

3. "Who else needs to be on board? Who can say no?"

↳ Map technical evaluators, political influencers, and status quo

4. "If trial goes perfectly, what results are needed?"

✱ Document required features, and business metrics

✱ Get written confirmation. Lock everything in place

4. "What might stop you after few successful trials?"

↳ Red flags: “We’ll see” or “Maybe next year.” 

↳ Secure with date commitments for clarity

5. Define success by lockinng agreements upfront

• Confirm technical, business, adoption goals in legal writing.

• Make stakeholders agree with meeting goals by a set date.

• Have legal review the agreements for clear post-trial delays.

6. Handle vendor objections before they surface

Ask early questions like:

➤ “How did your current vendor respond to challenges?”

➤ “What specific capabilities have they been lacking of?”

Document answers to strengthen business cases later.

7. Implementation from high-performing trials

✔ Run with fewer users, including decision-makers

✔ Do observation sessions for execs to view usage

✔ Mae weekly success updates against given metric

✔ Pre-schedule discussion before product trial start

5. Utilize“trial success kit” for more conversion

1. Decision matrix (stakeholder map)

2. Signed success criteria document

3. Current vendor analysis discussion

4. Weekly given progress dashboard

5. Sure purchase timeline agreement

Why demo features aren’t selling products

Denis Shatalin warns that most B2B SaaS reps kill their close rates by turning sales demos into 20–40 minute feature run instead of straightforward, outcome-driven conversations:

Establish discovery calls beforehand

✱ Identify their current situation, dream outcome, and gaps between them.

✱ Ranking customers main problems by linking with personal experiences.

✱ If you can’t do everything by then, don’t show customers anything yet.

Problems→ Solution → Outcomes

Example:

↳ “You said tax optimization this quarter is critical. With our automated invoicing, your tax criteria are always met across the finance team.”

Then subsequently check in:

“Does this get you closer to your desired goal?”

Repeat for the other problems

Example:

↳ “These features save 20–30 hours/week on manual quote creation, so you won’t need to hire extra staff, making it easier to grow your accounting firm by $3M next year.”

Target customers using problem-based solutions.

Why this works

❖ Focused, and Relevant: Every pillar ties directly with stated challenges.

❖ Ongoing Check-ins: Prevent sudden overwhelm, keeps them engaged.

❖ Prospect’s Language: Makes your connection feel natural, and specific.

❖ Outcome Framing: Supports higher pricing by attaching value to goals.

Keep demos from becoming a feature dump

Richard Harris provides the difference on presentations building trust and those missing on securing closed deals. Know how to present good demos, while avoiding bad ones:

Bad sales demo: Death by mouse click

A small business owner needs simple CRM tracking.

However, reps go into complex automations instead.

Instead, the rep could have started with:

➔ “Before we jump in, what are you hoping a CRM system will do for you? I have no desire to show things you don’t feel matter.”

Good sales demo: Prospects feel heard

A good demo is tailored for customer’s headspace.

Great solutions link features to problems experienced:

• Pre-demo Discovery – identify attendees, decision roles, key priorities, and skepticism points before starting discovery.

  
  Example:

  “What challenges are you facing now that you want to make sure we cover?”

• Prospect-centric Opening – use “assumptions we’ve made” slide with 5–7 reasons you think clients are potentially here for.

  Example:

  “What did we get right, what did we miss?”

• Engaging Narrative – establishes the product as hero in their story.

• Interactive Flow – stop yourself if you’ve been talking excessively.

  Example:

  
  “I’ve been talking for way too long. What questions do you have?”

• Visual problem-solving – help “see the bigger picture” by establishing the potential “after” state your offer will enable for them.

• Proactive Objection Framing – prioritize the urgent issues right away.

  Example:

  
  “Which might still be a concern for you?”

Example:

A SaaS company demos a project management tool for reps struggling with group collaboration.

The primary focus is on:

❖ Real-time project collaborations

❖ Integrations with existing stacks

❖ Custom dashboard for efficiency

Sales reps confirm their pain points, while asking for the “next challenges”.

Worst demo question possible:

Don’t ask prospects: “Does that make sense?”

This question usually get vague “yes” responses.

Better alternatives:

✱ “How does our solution compare to your way of doing things?”

✱ “What potential concerns have you been thinking of so far?”

✱ “Does this meet your objectives? What would make it a 10?”

✱ “How does this compare from what else you’ve seen publicly?”

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