Running High-Impact Customer Q&A Webinars that Drive Upsells
Designed for Customer Success Managers and Sales Enablement Specialists responsible for driving product adoption and upsell opportunities via customer-facing webinars to spark real collaboration and high-energy learning.
A 90-minute virtual workshop for CS and sales enablement teams at SaaS companies. These professionals are comfortable with presenting but struggle to convert live Q&A moments into upsell conversations without losing credibility or sounding salesy. The session focuses on practical tactics for making Q&A webinars feel authentic while opening doors for expansion.
Upsell Opportunity Mystery Reveal
Kick off with a quick poll: 'What percentage of our webinar attendees ever ask about advanced features?' Gather instant guesses, then reveal real company stats showing how often upsell signals appear in Q&A sessions. This sparks curiosity about what’s hidden in plain sight and primes minds for opportunity-spotting.
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Why this works
Curiosity gaps drive engagement; showing surprising data creates a puzzle participants want to solve, focusing attention on actionable insight.
Upsell Myths Busted
Facilitator shares three common misconceptions: e.g., 'You can’t mention upsells in a Q&A or you’ll lose trust,' 'Q&A is only for troubleshooting,' 'Premium features are for sales calls only.' Participants vote on which they’ve seen or believed, then discuss why these myths persist and how to reframe them.
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Why this works
Addressing misconceptions reduces internal resistance, allowing learners to adopt new approaches without fear or guilt.
Easy Upsell Icebreaker
Invite everyone to write (just for themselves) one upsell phrase they’re comfortable using during Q&A—no pressure to share! Then, ask volunteers to read theirs aloud if they wish. This low-stakes method builds confidence and surfaces practical language for the group.
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Why this works
Low-pressure participation lowers anxiety and allows cautious learners to experiment and reflect before risking public exposure.
Upsell Pitch Showdown
Split participants into breakout groups. Each group gets a real customer question (e.g., 'Is there a way to automate reporting?'). Teams brainstorm a 30-second Q&A response that subtly includes an upsell offer, then perform their pitch in rapid-fire succession. Fast, fun, and energizing.
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Why this works
High-energy competition activates creativity and keeps attention high, while group work helps participants practice skillful upsell language.
The Tough Question Twist
Present a dilemma: 'A customer asks, “How does this compare to the cheaper competitor?”' Invite the group to brainstorm how to address this honestly while pivoting toward upsell value, either via chat or quick round-robin. Explore different responses and discuss which build trust and which miss the mark.
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Why this works
Real-world dilemmas increase relevance and allow learners to problem-solve collaboratively, deepening their commitment to the skill.
Personal Upsell Action Commitment
End with a guided reflection: 'Think of your next webinar Q&A—what’s one upsell opportunity you’ll intentionally watch for and act on?' Have participants write their commitment on a sticky note (or digital post-it), then share with a partner or buddy for accountability.
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Why this works
Personal reflection and peer accountability increase follow-through and ensure new skills translate beyond the workshop.
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