Leading MultiGen Teams Through AI Change
It started with a time crunch.
The sales team was swamped, struggling to keep up with the volume of proposals. When a new AI tool came across the leadership team’s desk that could auto-generate client proposals in minutes, it felt like a no-brainer.
The decision was quick. The tool was rolled out the following week.
Training was optional.
The tone was, “This is the future, let’s go!”
And go they did. At least, some of them.
The younger half of the team jumped in with both feet. They had used generative AI before. They were curious, experimental, and comfortable with trial and error.
The more seasoned team members? They hesitated.
They didn’t push back outright.
But in the coaching sessions that followed, their language told a different story.
“I don’t want to send something that doesn’t sound like me.”
“My clients are used to a certain level of detail. I don’t want to miss something the bot overlooks.”
“Honestly, I feel like I’m being asked to trust a tool no one fully understands yet.”
Meanwhile, the newer team members were frustrated.
“They’re making it harder than it is.”
“We have to stop romanticizing the old way.”
“If we’re going to scale, we can’t treat every proposal like a novel.”
The tension wasn’t about the tool. It was about what it symbolized.
Speed versus nuance.
Efficiency versus trust.
Progress versus control.
The problem wasn’t that the AI didn’t work.
It was the rollout that ignored the human side of change.
There was no shared definition of what a “great” proposal looked like.
No space to voice what people were afraid of losing.
No pause to align on how the client experience would be preserved across automation.
The leader assumed the most significant risk was the tool failing.
But it wasn’t.
The risk was that, in trying to move fast, they never looked back to see who was struggling to keep up.
By the time the tension surfaced, it was already late.
And all of it could have been avoided with a better rollout. One that treated AI not just as a tool, but as a shift in how people work, communicate, and see their value.
If your team is wrestling with how to adopt AI without losing clarity, trust, or momentum, now’s a good time to subscribe. I’m delving into the same challenges I coach leaders through every week- real scenarios, real resistance, and how to lead effectively through them. This Wednesday, paid subscribers will get a rollout checklist for introducing AI within a multigenerational team, including how to anticipate pushback, build buy-in, and lead the change without leaving anyone behind.
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