You Might Try This – Details, episodes & analysis

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You Might Try This

Stacey Philpot and Cade Cowan

Business

Frequency: 1 episode/9d. Total Eps: 11

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.

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Score global : 73%

Publication history

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The Courage Tax: What you pay every time you delay the conversation that needs to happen

Season 1 · Episode 10

Monday, May 11, 2026 • Duration 28:34

Why do difficult conversations feel so much harder the longer we avoid them? In this episode, Stacey and Cade unpack the hidden “taxes” leaders pay when they delay hard conversations at work; from damaged relationships and declining performance to mental overload and unnecessary anxiety. They explore why silence often costs more than honesty. The conversation offers practical tools for leaders, including how to start difficult conversations, avoid climbing the ladder of inference, and use curiosity instead of judgment.

Takeaways

Avoidance has real costs
Silence is often misinterpreted
The story in your head is usually worse than reality
Start with observable facts, not assumptions
Choose the right opening

Chapters

00:00 The Cost of Avoiding Difficult Conversations

01:11 The Conversation You’ve Been Putting Off

03:05 The Hidden “Taxes” of Avoidance

06:50 Why Leaders Avoid Giving Feedback

08:22 The Cognitive Load of Unspoken Issues

10:26 Why Difficult Conversations Feel Worse Than They Are

17:52 How to Start a Difficult Conversation

If you’re a leader struggling to bring up hard topics, this is the episode for you.

To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis

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

Season 1 · Episode 9

Monday, May 4, 2026 • Duration 34:24

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 growth
High-effort, low-visibility work often stalls advancement
Saying yes to everything can reinforce the wrong professional brand
Strategic visibility matters more than constant execution
Ask 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.

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

Season 1 · Episode 8

Monday, April 27, 2026 • Duration 28:07

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 growth
Focusing on observable behavior instead of character judgments betters the feedback session
Avoid the feedback sandwich and lead with clarity
Use the SBI framework: situation, behavior, impact
Shift 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

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

Season 1 · Episode 7

Monday, April 20, 2026 • Duration 23:32

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 effectiveness
How rewriting work and “saving” your team reduces capability and trust
The difference between role modeling and coaching and why it matters
How fear, control, and identity protectiveness show up in new leaders
Practical 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)

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

Season 1 · Episode 6

Monday, April 13, 2026 • Duration 26:41

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

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

Season 1 · Episode 5

Monday, April 6, 2026 • Duration 27:35

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

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

Season 1 · Episode 4

Monday, March 30, 2026 • Duration 32:19

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 time
The trust equation breaks down trust into credibility, reliability, and intimacy
Self-interest can undermine trustworthiness
Effective leaders prioritize understanding others' needs
Building 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

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

Season 1 · Episode 3

Monday, March 23, 2026 • Duration 35:27

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

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

Season 1 · Episode 1

Monday, March 16, 2026 • Duration 26:13

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

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

Season 1 · Episode 2

Monday, March 16, 2026 • Duration 30:03

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

You Might Try This – Details, episodes & analysis

Podcast details

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Apple Podcasts

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You Might Try This – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Apple Podcasts

Spotify