Running Strategic Executive Roundtables that Generate High-Quality Leads
Designed for Enterprise sales leaders and senior account executives responsible for B2B pipeline growth, who are tasked with designing and facilitating executive-level roundtables targeting C-suite prospects. to spark real collaboration and high-energy learning.
A 90-minute, interactive, virtual workshop for experienced enterprise sales professionals who already host webinars and lunch-and-learns but struggle to engage executives authentically and convert those interactions into real sales opportunities. Participants are keen to differentiate from generic marketing events and deepen strategic value.
The Invite You Can’t Ignore
Kick off with a rapid-fire viewing of three real-life executive roundtable invitations—one stellar, one mediocre, and one ineffective. Participants use a poll to guess which invitation drove the most C-suite RSVPs, then see the real results.
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Why this works
Curiosity and contrast activate participants’ interest and help them internalize what actually works in a crowded inbox.
Pitch vs. Peer Myth-Busting
Present this statement: 'The most effective roundtables showcase your product’s features in detail.' Invite a quick thumbs-up/down response, then share data and a brief customer quote illustrating how overt pitching actually shuts down executive dialogue.
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Why this works
Revealing misconceptions helps learners let go of unhelpful habits and primes them for new paradigm thinking.
Roundtable Icebreaker Roulette
Each participant picks a digital card revealing a low-stakes, roundtable-style opener (e.g., ‘Share one business book that changed your thinking’). Volunteers try their opener out in small breakout groups, practicing how to spark authentic conversation.
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Why this works
Low-pressure participation boosts psychological safety, letting everyone practice facilitation in a fun, zero-risk way.
Lightning Roleplay: 'Subtle Spotlight'
In high-energy pairs, one person acts as the facilitator, the other as an executive participant. The facilitator must naturally weave a customer outcome or insight into the discussion—without sounding like a pitch. After 60 seconds, pairs swap roles.
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Why this works
Roleplay in a time-boxed, fast-paced format lowers anxiety and helps participants internalize subtle advocacy skills.
The Follow-Up Fork in the Road
Pose a real-world dilemma: After a great roundtable, a high-value executive goes quiet. Give participants three actual follow-up messages from previous campaigns. Small teams debate: Which approach is most likely to re-engage, and why?
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Why this works
Anchoring learning to a real-world dilemma helps participants connect knowledge to the exact ‘now what?’ moment they’ll face.
Personal Commitment Postcard
Ask each participant to write a short ‘postcard to future me’ stating the one roundtable action or tactic they commit to try within 2 weeks. Share a few aloud and invite volunteers to explain their choice.
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Why this works
Personal reflection and future-casting increase follow-through and connect learning to real-world action.
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