Library/Leadership, Coaching & People Management/Team Operating Cadence/Design a 90-Minute AI Selling Workshop for Sales Kickoff
TestedLeadership, Coaching & People ManagementQuick Win (under 10 min)

Design a 90-Minute AI Selling Workshop for Sales Kickoff

Generate a fully facilitated SKO workshop agenda on AI-powered selling with notes, exercises, and a shared team prompt

About this prompt

This prompt produces a complete 90-minute sales kickoff workshop design on AI-powered selling, including facilitator notes, materials, and expected outputs for each segment. It's for sales managers and directors who want reps leaving with prompts they'll use in the field that same week. Use it when planning an SKO, a QBR, or any team enablement session where you want hands-on AI practice rather than a presentation.SKO sessions on AI tools fail when they're demonstrations rather than practice — reps watch, nod, and change nothing. This prompt designs a 90-minute workshop that sidesteps that failure mode: after a brief case for AI, reps see three live prompts that solve real daily frustrations, then small groups build their own prompt for a scenario they chose, share it with the room, and contribute it to a team library before making a specific daily commitment. Provide [NUMBER] for team size to shape the small-group breakdown. Each of the six agenda segments comes with facilitator notes, materials needed, and expected output — so you can hand this directly to whoever is running the session. This prompt targets sales managers and directors planning a live team session; if you're designing asynchronous enablement, the 30-day adoption plan prompt (260615_keepers2_b16-0030) is a better fit. The live demo in segment two is the highest-stakes moment — pick three prompts that solve problems your reps specifically complain about, not problems you think they should have.

The prompt

Design a 90-minute sales kickoff workshop on 'AI-Powered Selling' for my team of [NUMBER] reps. The workshop should be practical — reps leave with prompts they use in the field that week. Agenda: 1.
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Variables to replace

NUMBER

How to run it

  1. Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
  2. Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
  3. Make it yours — run it, keep what's strong, and tighten your inputs on the next pass. The prompt improves with your context.

What good output looks like

Make it yours

StageOngoing/Cross-Stage
SeatSales Manager, Sales Director
DifficultyIntermediate
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryLeadership, Coaching & People Management
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