How to Interview Prospects for Your New Startup
Wednesday, November 19, 2025, 10:00 AM PST – 11:30 AM PST
Virtual event
Hosted by Perseverance Accelerator
1.5 Hours Online Practical Workshop by Rick Moy Stop pitching. Start learning. Turn conversations into product insight with UpSight. Most founders talk too much and learn too little. This workshop shows you how to stop selling and start asking better questions so you can understand the actual needs and wants of your supposed target users. We’ll practice live interviews and use UpSight to capture signals, emotions, and next steps you can act on. What you’ll learn How to switch from “convincing” to “curious” in sales and discovery calls Question patterns that uncover pains, goals, and real workflows How to treat early customers as beta testers and co-designers How to use UpSight to plan interviews, capture evidence, and turn it into clear decisions A repeatable structure for your next 10–20 prospect conversations Who this is for Early-stage founders and product builders Solo operators validating a new idea Sales/product folks running customer discovery or beta programs AGENDA 0–10 min – Welcome & mindset reset Why most founder interviews fail “Stop selling when you need to just ask questions” Customers vs. beta testers: what changes in your conversations 10–25 min – Foundations: how to ask better questions Bad vs good questions (leading, pitchy, hypothetical vs grounded) Core patterns: “Tell me about the last time…”, “Walk me through…”, “What else?” Small group reflection: common mistakes you make now 25–30 min – UpSight demo: from questions to insights Show an example project: goal → interview plan → evidence → insights Walk through: creating an interview guide in UpSight Show how evidence gets tagged (pains, goals, behaviors, emotions) 30–65 min – Breakout practice: run real interviews Pair up: one “founder”, one “prospect/beta tester” Use a simple UpSight interview template Founder practices: asking, not pitching Prospect roleplays real objections / messy reality Switch roles halfway Repeat 65–80 min – Debrief: what did we learn? Group share: best questions that worked, where you slipped into selling Show in UpSight: pulling themes from a few example notes Connect insights to next steps (product, messaging, pipeline) 80–90 min – Wrap-up & next experiments Your “next 5 interviews” plan Quick demo: how to keep using UpSight after the workshop Follow-up resources Meeting ID: 890 2776 4503 Passcode: 441157