“I Wish I’d Had This…”: My True Story as a Leader Who Could’ve Used AI Role-Play
There’s a series of conversations I still think about more than I’d like to admit.
It was with a direct report—a smart, ambitious guy who was hungry for a promotion and very proactive about asking for one. He brought it up constantly. The problem was, he wasn’t ready. He hadn’t demonstrated the leadership skills required for the next level, and he didn’t seem interested in growing into them, either. I’d suggest development opportunities, share resources, and remind him of his unused professional development. He’d nod along and smile. And then… nothing changed.
Eventually, he went over my head to lobby for the promotion directly with my senior leader (that didn’t work either). Regardless, our trust fractured and we never really repaired it. By the time I left my role, I think we were both pretty frustrated with each other.
When I look back on my time managing him, I have to face a hard truth about myself. I wasn’t direct enough. It was my first time managing, and I wanted to be encouraging! Supportive! I avoided saying, plainly, “You are not there yet, and unless you do XYZ, you will not get there.” I wasn’t firm. I wasn’t clear. And I definitely didn’t practice the conversations before they happened.
Enter: Regret—and Then, a Better Way
This is one of the reasons I love building for Tenor.
We don’t talk enough about how hard these kinds of conversations are. How easy it is to overcorrect either by being too soft and vague, or too blunt and cold. How few chances we get to say it right, and how rarely we get the feedback we need to course-correct in time.
Tenor’s AI-powered role-play scenarios are designed for exactly this: the conversations that feel high-stakes and high-risk, but that don’t come with a rehearsal button.
With Tenor, I could’ve run those conversations with an AI character first. I could’ve tried a few approaches, seen how they landed, and gotten feedback on tone, clarity, and alignment with best practices. I could’ve adjusted. Learned. Tightened my language. Prepared for resistance.
Maybe it still wouldn’t have gone perfectly, but I would’ve gone in more grounded, more practiced, and more clear. Ultimately, I think my relationship with my direct report would have been all the better for it, too.
And I wouldn’t still be haunted by my mistakes.
And it seems I’m not alone. When I meet someone new and tell them about what Tenor does, almost every time the reaction I get is a variation of,”Wow! There were many times in my career I could have used that. I made some big mistakes in some important conversations.”
We Don’t Need Perfect. We Need Practice.
Tenor wasn’t built to replace instinct or empathy, it was built to hone them.
Because the best way to show up better for the real conversation is to try it first somewhere safe. Somewhere that gives you space to stumble, regroup, and try again—before it really counts.
If you’ve ever walked away from a hard conversation thinking, I wish I’d said that differently, you know what I mean.
We built Tenor so that next time, you can.