I personally have definitely come to stakeholder meetings with a lot of baggage of my own. Iāve felt defensive before the conversation even starts. Iāve spent a lot of time worrying about what happens if we disagree. Whoās going to make the call? Whose call is it? Iāve lost quite a few hours of sleep catastrophizing and replaying in my head past conversations and whatās going to happen.
Most of my relationships with stakeholders are good. Theyāre not free of conflict, but the conflict is the kind that strengthens us. However, I think all of us PMs can relate to having at least one or two stakeholders where itās really hard to get that relationship off the ground or build that emotional bank account to establish trust. Those conversations just donāt naturally get easier.
Weāve all heard the phrase āhave the meeting before the meetingā ā now weāre going to do that with AI. The way weāre going to practice and improve our skills is in two ways.
First, weāre going to have AI play the stakeholder and simulate the other person while we talk to them.
Then weāre going to turn things around and have AI play us while we play the stakeholder.
The goal is that we arrive at the real meeting more emotionally mature, more prepared, feeling much more open to genuine empathy. The most important thing of any conversation, regardless of the action items or results, is that the other person feels genuinely heard.
Iām going to simulate a stakeholder meeting with a scenario I definitely made up and has never happened to me: Marketing has some ideas for the onboarding.
Using my copilot playbook in Claude (ChatGPT has projects, Gemini has gems - itās just a nice way of organizing things and giving context), I start with: āHelp me simulate a stakeholder meeting with the new head of marketing Frank and prepare me in advance. Frankās been at the company a few months, has ideas for onboarding, wants them prioritized on the near-term roadmap.ā
Frank opens: āThanks for making time. Iāve been diving into our flows and seeing a lot of drop-off. Iād love to get these prioritized.ā
My response: āHey Frank, thatās really awesome. Iām so excited youāre thinking so deeply about this and Iād love to hear the ideas. I will say that Iām getting a little nervous because we just have so much planned this quarterā¦ā
The AI coaches me: āYouāre being polite, but youāre starting with caution rather than curiosity. Try to first understand the full context.ā
Frank mentions theyāve done homework, created proposals, sketched designs - āI think we just need two to three weeks of engineering time.ā The ultimate trigger sentence for a PM.
I stay resistant: āIt sounds like you guys have really dug into thisā¦ but I will say, I just really feel that we should have our eyes towards the next quarter.ā
The coach calls me out: āYouāre still in a defensive posture rather than exploratory.ā
I go completely off track: āListen, weāre doing what the CEO told us to do, so you should take it up with him.ā The AI gives me yellow and red cards.
Then I flip it: āIād like to be Frank, and you simulate me.ā Now Iām saying Frankās words - about having ideas, seeing low-hanging fruit, wanting to partner. Just saying that out loud, I can feel it in my body.
The AI shows what an ideal PM would say - taking notes, showing genuine interest. If the Dalai Lama was a PM, this is what he would say.
Even though Frank isnāt real and this was a complete simulation, I feel it affect me every time.
ā”ļø Use AI to simulate both sides of difficult stakeholder conversations. Practice being yourself AND seeing through their eyes. The emotional preparation matters more than the perfect script. AI simulation creates a safe space to feel your defensiveness, practice curiosity and literally embody your stakeholderās perspective. The emotional rehearsal is as valuable as the tactical preparation.
Soft skills & hard conversations
Simulate a hard conversation
Use AI to rehearse - as both sides.