Aaron Wilkerson has spent nearly two decades in data and analytics — working his way up from individual contributor to Director of Data Strategy and Product at Carhartt. In this conversation, he pulls back the curtain on what leadership actually looks like from the other side: how directors prioritize requests, what it really means to bring an idea to your manager, why staying comfortable in your role is a quiet career risk, and why even senior leaders are figuring out AI as they go.
If you've ever wondered what your manager is thinking — this episode is for you.
In this episode:
Why there's no single "right answer" in data work
How to bring ideas to leadership in a way that actually gets traction
What directors look for when prioritizing analyst requests
The difference between AI and automation (and why it matters for your career)
Why building empathy for your manager can change everything
Follow Aaron on LinkedIn:
https://www.linkedin.com/in/aaron-wilkerson-81bb21a/
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The Quietly Ambitious Analyst–where business context meets data communication.
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