The old order isn’t coming back, traditional leadership development is not enough…
June 17, 2025
“My business needs to achieve X. I’m being asked to do Y. What would you do if you were me?”
That was the question posed by Eileen Cooke, Chief Learning Officer at Amtrak, during the opening session of last week’s CLO Exchange in Boston.
And it was brilliant.
In a single prompt, she captured the heart of what the entire gathering was about.
The first part, “My business needs to achieve X,” reminds us that L&D is not a side function. It’s core to performance. As Cooke put it, this work isn’t just about helping people learn for the sake of development or providing essential skill training. It’s about enabling results. Learning leaders exist to propel the business forward.
The second part, “I’m being asked to do Y,” names the real-world tension. This is where leaders navigate messy dynamics and try to decide which levers to pull. Is this a training challenge? A culture issue? A systems gap? A failing process? Or a matter of priorities and timing?
And then comes the final part: What would you do if you were me?
That’s where the magic happens.
It’s a humble, human question. It works best when you’re surrounded by people you trust – people who are thoughtful, honest, and doing the work. It invites dialogue rather than defensiveness. Empathy instead of ego. It helps bridge the gap between intention and impact, and builds the kind of brain trust every leader needs.
From that opening session on, the prompt echoed through nearly every hallway conversation and panel discussion. It surfaced again and again as leaders explored how to support teams, prioritize the right capabilities, and make learning actually stick.
It also reminded me of Leaps.
Leaps live at the intersection of what the business needs (X) and how a person needs to grow to make an impact (Y). They unfold within a cohort of peers who support, challenge, and learn from one another.
In other words, it’s not just about understanding the problem you need to solve. It’s identifying how you need to grow in order to solve it. And then leveraging the people around you as support.
So this week, try building your own brain trust. Fill in the blanks below, then share it — on LinkedIn or with a trusted friend or group:
My business needs to achieve ___. I’m being asked to ___. What would you do if you were me?
It might open a conversation you didn’t know you needed. And it just might unlock your next step.
Erin and me and our crew of Chief Learning Officers at Little Donkey in Cambridge, MA.
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