Use AI to uncover what your stakeholders really care about before you write your update or proposal.

Before you write that project update, proposal, or request for approval, you usually guess what your audience wants to know. But what if you could map out their actual concerns, priorities, and likely objections first — then tailor your message to answer exactly those points? This technique uses AI to role-play as each of your key stakeholders and reveal what matters most to them. You give ChatGPT a few details about each person — their role, what they're responsible for, what keeps them up at night — and ask it to voice their perspective. The result is a detailed "concern map" that shows you what each person will focus on when they read your message. Once you see their concerns laid out, you can structure your update or proposal to address them directly, in priority order. Instead of writing a generic message and hoping it lands, you're speaking directly to what each stakeholder actually cares about. Your message becomes shorter, sharper, and far more persuasive — because you've done the empathy work upfront.

February 23, 2026