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Transformative Leadership Conversations with Winnie da Silva

Transformative Leadership Conversations with Winnie da Silva

By: Winnie da Silva
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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.Copyright 2026 Transformative Leadership Conversations with Winnie da Silva Career Success Economics Leadership Management Management & Leadership
Episodes
  • Ruthlessly Prioritize Today
    Oct 28 2026

    Everyone has an opinion on what you should be doing, and that’s exactly why it’s so hard to figure out what actually matters.

    In this episode of Winnie Unscripted, I’m using fall as a reason to step back and get honest about priorities. I share the simple way I connect the dots between what the company needs, what my boss cares about, and what I really want to work on, so I can find the one essential thing. My advice is to skip the big annual plan for now and just start with today.

    Resources

    Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

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    3 mins
  • The Promotion Free Fall
    Oct 21 2026

    The pressure to prove you deserve a promotion can actually be the very thing holding you back. And here's the kicker: that pressure doesn't always disappear once you get promoted.

    In this episode, I'm talking about the anxiety and self-doubt that come with promotions and why constantly trying to prove your worth can undermine your confidence. I share an analogy about the uncomfortable feeling of free fall during career transitions and explore how to recognize where insecurity comes from, shift the stories we tell ourselves, and embrace the idea that sometimes, less really is more.

    Resources

    Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

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    4 mins
  • Should I Stay or Should I Go?
    Oct 14 2026

    Should I stay or should I go? How long is too long to wait for that next promotion, bigger opportunity, or the recognition I've been working toward?

    It's a question I'm hearing more and more from my clients, especially as the job market gets tougher and the decision to leave a company isn't so straightforward. In this episode, I'm digging into the growing issue of mid-career stagnation, sharing what I'm seeing with clients who are weighing loyalty against new opportunities, why staying isn't necessarily a bad move, and why leaving isn't always the answer either.

    Resources

    Burning Glass Institute - "Sidetracked: The Hidden Crisis in Mid-Career Mobility"

    Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

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    5 mins
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