You Might Try This

Stacey Philpot and Cade Cowan
  • 5.0 (3)
  • MANAGEMENT
  • WEEKLY SERIES

Leadership is complicated, especially when you’re figuring it out in real time. You Might Try This is a weekly podcast for people who want to lead well without , burning out, selling out, or pretending they have it all figured out. Hosted by executive coaches Stacey Philpot and Cade Cowan, the show brings decades of experience working with leaders at global brands like Nike, Google, Walmart, and Microsoft into honest, practical conversations about what leadership really looks like day to day. Each episode explores the messy, human side of work, from managing your first team and navigating power dynamics to building confidence, handling conflict, and staying grounded in high-pressure environments. Through real stories, proven frameworks, and thoughtful coaching, Stacey and Cade offer tools you can actually use, not just theories that sound good on paper. If you’re ambitious, thoughtful, and trying to grow your career while staying true to yourself, this show is for you. New episodes drop weekly. Listen wherever you get your podcasts and join the conversation on Instagram @YouMightTryThis.

Season 1

  1. EPISODE 1

    The Authenticity Paradox: Why "bringing your whole self to work" is a leadership disaster

    Welcome to You Might Try This! In this episode, Cade Cowan and Stacey Philpot unpack what authenticity really looks like in leadership, challenging common assumptions about transparency and vulnerability. They discuss why authenticity must be intentional and selective, the role of boundaries in professional relationships, and how leaders can stay grounded in who they are while adapting to different responsibilities. Takeaways: Authenticity is frequently mistaken for total transparency.Being “more authentic” does not automatically create stronger relationships.Authenticity should be shaped by context, audience, and role.Vulnerability can build connection, but it works best after trust and competence are established.Authentic leadership requires flexibility and a willingness to evolve.Strong professional relationships depend on clear, well-defined boundaries. Chapters 00:00 Introduction 1:09 Myth One: Authenticity is the same thing as transparency 8:31 Myth Two: The more authenticity, the better 11:32 Myth Three: Authenticity is all about staying true to your past self. 14:53 Creating boundaries 21:46 What You Might Try To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #leadership #Authenticity #coaching

    26 min

  2. EPISODE 2

    The Promotion Deficit: Why becoming a boss feels more like a loss than a reward

    In this episode of You Might Try This, Cade Cowan and Stacey Philpot unpack the realities of stepping into leadership, especially the emotional and mental shifts that often come with a promotion. They explore why new leaders can feel isolated and overwhelmed, even when the role they worked hard for finally arrives. The conversation dives into the complex contrast of the excitement of moving up with the weight of added responsibility, changing relationships with former peers, and the pressure of managing expectations from all sides. Cade and Stacey also talk about the loneliness that can come with leadership and the trust gap that often appears when someone transitions from teammate to manager, offering insight into how organizations can better support people in these moments. Takeaways Leadership can feel isolating, especially when responsibilities and expectations increase.Promotions often bring emotional challenges that aren’t always anticipated.Trust can shift when moving from peer to manager, requiring careful navigation.New managers must adjust how they see themselves and how they lead others.Effective leadership is rooted in helping others grow and make meaningful progress. Chapters 00:00 Introduction 1:27 The Isolation of leadership 6:34 Earning authority and building trust 11:59 The SCARF model 22:16 Founder mentality and relational leadership 25:56 What You Might Try To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #leadership #Authenticity #coaching

    30 min

  3. FEB 5

    You Might Try This - Trailer

    Coming soon... a new podcast—You Might Try This! Leadership is complicated, especially when you’re figuring it out in real time. You Might Try This is a weekly podcast for people who want to lead well without , burning out, selling out, or pretending they have it all figured out. Hosted by executive coaches Stacey Philpot and Cade Cowan, the show brings decades of experience working with leaders at global brands like Nike, Google, Walmart, and Microsoft into honest, practical conversations about what leadership really looks like day to day. Each episode explores the messy, human side of work, from managing your first team and navigating power dynamics to building confidence, handling conflict, and staying grounded in high-pressure environments. Through real stories, proven frameworks, and thoughtful coaching, Stacey and Cade offer tools you can actually use, not just theories that sound good on paper. If you’re ambitious, thoughtful, and trying to grow your career while staying true to yourself, this show is for you. New episodes drop weekly. Listen wherever you get your podcasts and join the conversation on Instagram @YouMightTryThis.

    1 min
  • 3 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

Leadership is complicated, especially when you’re figuring it out in real time. You Might Try This is a weekly podcast for people who want to lead well without , burning out, selling out, or pretending they have it all figured out. Hosted by executive coaches Stacey Philpot and Cade Cowan, the show brings decades of experience working with leaders at global brands like Nike, Google, Walmart, and Microsoft into honest, practical conversations about what leadership really looks like day to day. Each episode explores the messy, human side of work, from managing your first team and navigating power dynamics to building confidence, handling conflict, and staying grounded in high-pressure environments. Through real stories, proven frameworks, and thoughtful coaching, Stacey and Cade offer tools you can actually use, not just theories that sound good on paper. If you’re ambitious, thoughtful, and trying to grow your career while staying true to yourself, this show is for you. New episodes drop weekly. Listen wherever you get your podcasts and join the conversation on Instagram @YouMightTryThis.

Information

  • Creator
    Stacey Philpot and Cade Cowan
  • Episodes
    3
  • Seasons
    1
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Stacey Philpot and Cade Cowan
  • Show Website
    You Might Try This

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