Play 3: Partner with a Skeptical Executive
Every org has one: the exec who’s still unsure if AI is signal or noise. Instead of avoiding them, turn them into a partner. Invite them into an experiment where you experiment with AI within their function.
When skeptics see results tied to their goals, their resistance turns into advocacy. And once an executive becomes a public backer, org-wide momentum shifts easier.
Examples:
- Use AI to generate board-ready business updates summarizing GTM KPIs, trends, and risks
- Use AI to surface team performance patterns (e.g., rep activity vs. conversion, funnel drop-offs, coaching gaps) with actionable next steps
Common Objection:
“I’m just not sure this is ready for the level of visibility it will receive.”
How to respond:
That’s exactly why we test it quietly now, with clear guardrails. We’re not rolling this out to the board or entire team tomorrow. We’re pressure-testing it with your context, on your terms. If it works, you’ve got leverage, and if it doesn’t, we’ve de-risked early. Either way, we learn faster than waiting on a perfect solution.
