At my previous company, I used to share a story during onboarding.

It wasn’t about a big win. It was about a mistake.

In my first two months, I made a critical error. The details matter less than the response: my leaders at the time handled it with grace, empathy, and a forward-looking mentality. We didn’t sweep it under the rug, but we also didn’t spiral into blame. We focused on understanding what went wrong and where systemic improvements could make us stronger.

I told this story for two reasons:

  1. We’re human, and we’re all learning. Especially in R&D on the bleeding edge of innovation: no one has done this before, mistakes will happen.
  2. We tackle challenges together. Forward-looking, constructive, and with an eye toward improving the system, not punishing the individual.

By openly sharing my own mistake, I wanted new team members to know that psychological safety here is real. You don’t have to hide mistakes (and you really shouldn’t). You can admit them, learn, and grow, and in fact, that’s how we become resilient together.

That’s what “modeling humanity” means. It’s not oversharing. It’s showing that being human is allowed, and that’s how teams actually thrive.

Augmenting your humanity with AI

Now imagine if AI could help leaders do this more often and more effectively.

  • Onboarding Story Builder: Capture and distill real mistakes into stories of learning and resilience that new hires hear on day one.
  • Conversation Practice Lab: Roleplay tough moments (admitting uncertainty, apologizing, giving feedback) so leaders and teams build muscle memory for psychological safety.
  • Reflection Nudges: Tools like Microsoft 365 Copilot could surface subtle signals from our own communications, when humility or openness is showing up and when it’s missing, giving us all a chance to do better.

AI can help us practice, remember, and retell the moments that remind teams that humanity is not a weakness.

Question for you: If you could AI-ify one thing about modeling humanity as a leader, what would you want AI to support? Join the conversation on LinkedIn.