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September 29, 2025 26 mins

What if leadership isn’t something you’re born with? In this episode, Alyssa sits down with Jen Silva Boucher to explore why leadership is a skill you can learn, practice, and grow.

Jen shares her own origin story of moving from individual contributor to people leader, the struggles of being a first-time manager, and how she built For the Middle Academy to support others in the same place. Alyssa and Jen talk openly about the mindset shifts, the importance of communication, and why middle managers are often the most overlooked but most important leaders inside a company.

This conversation will challenge how you think about leadership and leave you with practical ideas you can use right away.

3 key takeaways:

  1. Leadership is not a personality trait — it’s a set of skills that can be developed.
  2. Middle managers need resources and support just as much as executives and individual contributors.
  3. Great leaders adapt to their teams instead of expecting teams to adapt to them.

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