You Might Try This

Stacey Philpot and Cade Cowan
  • 5.0 (17)
  • 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. EPISODE 3

    The Logic Illusion: Why facts and ROI fail to win real commitment

    In this episode, Cade Cowan and Stacey Philpot talk about what influence really means in leadership and why it often matters more than having a title. They explore the idea of leading beyond your role and how real influence comes from how you relate to people, not the authority you’re given. Stacey breaks down the difference between “pushing” influence versus “pulling” it, sharing why influence works best when you focus on understanding what others care about instead of trying to persuade or control them. They also touch on common assumptions we make at work, like jumping to conclusions about people’s intentions, and how those habits can quietly undermine communication. Takeaways: Lead the way you wish leadership showed up for you, not just the way it’s modeled around you.When you push, you might get compliance, but not real buy-in.Influence grows when you understand people’s goals, concerns, and circumstances.Most people are looking for fairness and a sense of give-and-take.Leading with grace can strengthen trust and working relationships.How well you listen directly affects how much influence you have.Good communication creates value instead of friction. Chapters 00:00 introduction 01:39 Leading without authority: influence vs persuasion 06:10 The fundamental attribution error and workplace misunderstandings 11:20 Push vs pull communication: why curiosity works better 15:00 Understanding people: purposes, concerns, and circumstances 20:40 Power dynamics at work: role, expertise, and relationships 31:45 What to try: practical influence strategies that work To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #leadership #communication #persuasion

    35 min

  4. EPISODE 4

    The Trust Equation: Why social capital isn't a "vibe"—it's a calculated asset

    In this conversation, Stacey and Cade take a closer look at social capital and why trust sits at the center of it. They break down what trust really means in practice, introducing the trust equation and its core components: credibility, reliability, and intimacy. The discussion also examines how self-interest can either strengthen or undermine trust, depending on how it shows up in our actions and decisions. Together, they explore how these dynamics play out in leadership and everyday relationships, from building influence to maintaining strong professional connections over time. The conversation offers thoughtful, practical insights into how trust is earned, how it can be damaged, and what it takes to intentionally build and sustain social capital in meaningful, lasting ways. Takeaways: Trust is an asset that accumulates over timeThe trust equation breaks down trust into credibility, reliability, and intimacySelf-interest can undermine trustworthinessEffective leaders prioritize understanding others' needsBuilding trust requires a balance of generosity and reliability Chapters 03:08 Understanding the trust equation 06:54 Credibility and leadership perception 11:05 Reliability and keeping commitments 13:47 Building connection and psychological safety 24:53 Givers, takers, and building social capital To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #leadership #credibility #trust

    32 min

  5. EPISODE 5

    The Delegation Bottleneck: Why your desire to "help" is secretly stalling your team

    Delegation is one of the most important leadership skills, and one of the hardest to master. In this episode of You Might Try This, executive coaches Stacey Philpot and Cade Cowan unpack why delegation creates so much discomfort for managers and leaders, and how shifting from assigning tasks to delegating responsibility can transform your team, your leadership impact, and your workload. In this episode, you’ll learn: • Why delegation is about responsibility, not just tasks • The emotional barriers that make delegation so difficult • How poor delegation creates burnout and bottlenecks • A three-part framework for delegating effectively • How to launch work in a way that builds trust and ownership • Why asking better questions leads to better outcomes Chapters 03:09 Distinguishing tasks vs. responsibilities in delegation 06:00 Common fears leaders experience when delegating 10:52 Stacey’s three-part rubric for effective delegation 16:35 Asking questions to guide and support delegated work 24:34 Key takeaways: delegating as a process, not a one-off conversation To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #delegation #leadershipdevelopment #managementskills

    28 min

  6. EPISODE 6

    The Harmony Illusion: Why a nodding team is more dangerous than a resisting one

    When leaders encounter resistance, the instinct is often to push harder, explain more, or shut down the conversation entirely. But what if resistance is actually a sign of engagement and silent agreement is the real danger? In this episode, Stacey and Cade unpack why a nodding team can be more harmful than a resistant one, and how leaders can turn pushback into energy, insight, and momentum. What You’ll Learn: • Why resistance is a sign of engagement, not failure • How stress responses like control and avoidance shape leadership behavior • The hidden dangers of “artificial harmony” and passive agreement • How to work effectively with skeptics, protectors, experts, and silent resisters • Practical questions leaders can use to turn resistance into insight and buy-in Chapters 00:00 Why every leader faces resistance 03:08 Your stress response is making it worse 05:09 Resistance vs. apathy (this changes everything) 09:58 The 4 types of people who push back 16:17 How to turn resistance into buy-in To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis #leadership #management #workplaceculture

    27 min

  7. EPISODE 7

    The Expert Trap: How being the smartest person in the room can become your biggest liability

    In this episode of You Might Try This, hosts Stacey Philpot and Cade Cowan explore a critical leadership shift many high performers never see coming: when the skills that earned you a promotion start holding you back. They unpack the “expert trap”: how relying too heavily on your own expertise can turn you into a bottleneck, undermine your team’s confidence, and quietly derail your leadership trajectory. Through real-world examples and research-backed insights, Stacey and Cade explain why rewriting your team’s work, stepping in too fast, or role-modeling instead of coaching can erode trust, limit growth, and prevent future promotions. This conversation dives into the identity shift required when moving from individual contributor to leader, the hidden costs of control, and why organizations promote leaders who build successors, not bottlenecks. You’ll also hear practical strategies for delegating without disengaging, coaching without rescuing, and creating real ownership across your team. In this episode, you’ll learn: Why being an expert can quietly damage your leadership effectivenessHow rewriting work and “saving” your team reduces capability and trustThe difference between role modeling and coaching and why it mattersHow fear, control, and identity protectiveness show up in new leadersPractical ways to delegate, build successors, and scale your impact Chapters 00:00 When your strengths start holding you back 01:15 The promotion shift no one explains 02:53 How experts become bottlenecks 09:16 The gap leaders don’t see (and why it matters) 12:05 Why you won’t get promoted without a successor 17:22 How to stop overworking and start leading If you’re an emerging leader, newly promoted manager, or ambitious professional aiming for your next level, this episode will help you rethink how you create value and what to let go of to grow. #leadership #management #careergrowth

    24 min

  8. EPISODE 8

    The Feedback Friction: Why “constructive criticism” usually constructs a wall

    In this episode of You Might Try This, Stacey Philpot and Cade Cowan explore why leaders avoid giving feedback. They break down the psychology behind feedback fear, including how negative feedback triggers a real pain response in the brain and threatens identity. Challenging outdated methods like the feedback sandwich (also known as a sh*t sandwich), they introduce practical tools like the SBI (situation-behavior-impact) framework, an “adjective ban,” and feedforward strategies. The result: clearer, more constructive conversations that build trust, improve performance, and turn feedback into a powerful tool for leadership growth. Takeaways Clear, direct feedback builds trust and supports growthFocusing on observable behavior instead of character judgments betters the feedback sessionAvoid the feedback sandwich and lead with clarityUse the SBI framework: situation, behavior, impactShift the conversation toward future improvement Chapters 1:01 – Why leaders avoid feedback 7:23 – Selfishness and moral contagion 10:57 – Neuroscience of negative feedback 17:44 – Fundamental attribution error 20:06 – Adjective ban and SBI model 25:03 – Three experiments to try If you’re an emerging leader, newly promoted manager, or ambitious professional aiming for your next level, this episode will help you rethink how you create value and what to let go of to grow. #leadership #management #feedback

    28 min

  9. EPISODE 9

    The Good Soldier Trap: Why being dependable can become a liability with LaToya Jordan

    In this episode of You Might Try This, Stacey Philpot and Cade Cowan welcome Executive Coach and She Leads and Succeeds host LaToya Jordan for a powerful conversation about the “good soldier” trap: the career pattern where being dependable, helpful, and highly capable can quietly limit long-term growth. Together, they unpack how high-performing professionals, especially women, can become boxed in by their own excellence as executors, fixers, and problem-solvers. From “office housework” to low-visibility, high-effort tasks, the episode explores why saying yes too often can keep leaders stuck in support roles rather than strategic ones. Takeaways Working harder can become the ceiling that limits career growthHigh-effort, low-visibility work often stalls advancementSaying yes to everything can reinforce the wrong professional brandStrategic visibility matters more than constant executionAsk questions before saying yes to new work Chapters 00:00:00 – The hidden cost of saying yes 00:01:15 – When hard work stops working 00:02:24 – The good soldier trap 00:06:24 – Office housework & invisible labor 00:09:00 – Every yes is a tradeoff 00:11:53 – How to say no (without damage) 00:17:48 – From note-taker to thought partner 00:21:09 – Auditing your work & shifting perception 00:23:56 – What leaders really look for 00:28:13 – Experiments to change your trajectory If you’ve ever wondered why hard work alone isn’t translating into advancement, this episode offers the language, frameworks, and courage to rethink what you say yes to. #executivecoaching #careeradvancement #growth

    34 min

  10. 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
  • 10 Episodes

5
out of 5
17 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
    10
  • Seasons
    1
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Stacey Philpot and Cade Cowan
  • Show Website
    You Might Try This

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