Work-Bench is a NYC-based $160M enterprise software Seed stage VC fund. If you are or know anyone thinking about founding an enterprise/vertical AI or infrastructure startup - we’d love to meet! Please reach out to chat.
💡 THE TIP
The best demo question is not "any questions?" It is "if this were yours, what would you do with it?"
When Nick Cegelski runs demo calls, there is one question he’s found to improve prospect engagement. Instead of narrating through a screen and stopping to ask “any questions?”, he asks prospects to hold the product: “If you were looking at this dashboard, which KPIs would you drill into first?” or “Where would you integrate this into new hire onboarding?” or “What data here would you want to show your COO?”
The question does two things. It gets the prospect to picture life after they sign, and it surfaces real signal about how they would actually use the product. That is more useful than anything “any questions?” would ever uncover.
Special shoutout to Nick Cegelski for this tip! Read his full post here.
✅ THE TO-DO
Before your next demo, pick one screen and write a “hold” question for it specifically. Not “any questions?” but something like “if you were running this report, what would you be looking for?” Use it once and watch how the conversation shifts.
If you found this tip helpful, please share with a fellow b2b founder 😎
🤖 THE CLAUDE SKILL
Paste this into Claude before your next demo to generate a full set of “hold” questions for every screen you plan to show.
You are a sales coach helping me prepare demo questions that get prospects
to envision using my product.
My product: [ONE OR TWO SENTENCES ON WHAT IT DOES]
My typical buyer: [ROLE, COMPANY SIZE, INDUSTRY]
Screens or features I plan to show in my next demo: [LIST 3-5]
For each screen or feature I listed, write one "hold" question I can ask
the prospect mid-demo. Each question should:
1. Invite them to imagine they already own the product
2. Be specific to that screen or feature, not generic
3. Surface how they would use it in their actual workflow
Format: [Screen / Feature]: [Question]
Then give me one fallback "hold" question I can use on any screen if I
go blank mid-demo.📰 For Your Additional Reading
Last week we published our Work-Bench AI Snapshot report covering the biggest developments in tech and AI over the first half of the year. Visit our blog post here to download the full report and join us July 1 at 1pm ET for our webinar — signup here.
Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.