Side Hustle School Ep. 3244 - Q&A: “How do I upsell without sounding pushy?”
Nov 18, 2025
Discover how to upsell without coming off as pushy! Learn key principles such as timing and clear outcomes to make your offers feel natural. Hear a real-life dilemma from a copywriter about spotting client issues while fearing pressure tactics. Unlock a two-step framework that helps you diagnose problems before proposing solutions. It's all about making the upsell a win-win for both you and your clients!
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Episode notes
Copywriter Notices Client Funnel Gaps
- Leela describes writing copy for clients who then reveal larger funnel problems she could fix.
- She feels awkward offering audits because it makes her feel like a pushy used-car salesperson.
Two-Step Upsell Framework
- Lead with a short diagnostic step before offering fixes to clients.
- Offer a fixed-scope, outcome‑anchored solution tied to revenue impact so clients can easily say yes.
Framing Upsells As Responsible Help
- Pointing out a client's problem can be framed as responsible help rather than pushing an extra sale.
- Timing, evidence, and clear outcomes turn an upsell into an obvious win for everyone.