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

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:

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

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:

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

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

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

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:

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

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.