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

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.

#executivecoaching #careeradvancement #growth

Challenging outdated methods like the feedback sandwich (also known as a sh*t sandwich), they introduce practical tools like the SBI (situation-behavior-impact) framework, an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 #feedback

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:

1. Why being an expert can quietly damage your leadership effectiveness
2. How rewriting work and “saving” your team reduces capability and trust
3. The difference between role modeling and coaching and why it matters
4. How fear, control, and identity protectiveness show up in new leaders
5. 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)

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

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

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

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:

1. Trust is an asset that accumulates over time
2. The trust equation breaks down trust into credibility, reliability, and intimacy
3. Self-interest can undermine trustworthiness
4. Effective leaders prioritize understanding others' needs
5. 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

#leadership #credibility #trust

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:

1. Lead the way you wish leadership showed up for you, not just the way it’s modeled around you.
2. When you push, you might get compliance, but not real buy-in.
3. Influence grows when you understand people’s goals, concerns, and circumstances.
4. Most people are looking for fairness and a sense of give-and-take.
5. Leading with grace can strengthen trust and working relationships.
6. How well you listen directly affects how much influence you have.
7. 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

Takeaways

1. Leadership can feel isolating, especially when responsibilities and expectations increase.
2. Promotions often bring emotional challenges that aren’t always anticipated.
3. Trust can shift when moving from peer to manager, requiring careful navigation.
4. New managers must adjust how they see themselves and how they lead others.
5. 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

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:

1. Authenticity is frequently mistaken for total transparency.
2. Being “more authentic” does not automatically create stronger relationships.
3. Authenticity should be shaped by context, audience, and role.
4. Vulnerability can build connection, but it works best after trust and competence are established.
5. Authentic leadership requires flexibility and a willingness to evolve.
6. 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

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.