You Might Try This artwork

Management · Stacey Philpot and Cade Cowan

You Might Try This

by Stacey Philpot and Cade Cowan

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.

Latest episodes

Showing 20 · updated from the feed

The Politics Paradox: What’s really happening to leaders who say they don’t play politics

What does it really mean to “play politics” at work? In today’s episode, Cade and Stacey challenge the idea that organizational politics is something good leaders shoul

Aug 31
23 min

The Lateral Challenge: Why leading your peers is harder than leading your team

Working with your peers can be one of the hardest parts of leadership. You may have no authority over them, yet you still need their support to get things done and someti

Aug 24
27 min

The Name in the Room: The power of people who advocate for you

What moves a career forward: great advice or someone willing to advocate for you? In this episode, Cade and Stacey explore the critical difference between mentors and spo

Aug 17
17 min

The Visibility Paradox: Why the leaders who get noticed most aren’t the ones trying hardest to be seen

Why do some talented people get overlooked while others seem to attract every opportunity? In this episode, Stacey and Cade explore why great work doesn't always speak fo

Aug 10
26 min

Truth Before Optimism: Shawn Quinn on why leaders must honor hard truth before reaching for hope

Leadership can be lonely, uncertain, and emotionally exhausting… but we rarely talk about pain at work. In today’s episode, Shawn Quinn shares his research on professiona

Aug 3
53 min

The Age of Assumptions: How generational stereotypes cost you more than generational difference ever will

In today’s episode of You Might Try This, Stacey and Cade explore how assumptions about age shape the way leaders see, support, and develop their teams. They unpack why g

Jul 27
29 min

Belonging Is a Practice: Why Great Leaders Build Inclusion Intentionally

In today’s episode, Cade and Stacey explore why a sense of belonging is one of the most important, but overlooked, drivers of team performance. They explain that employee

Jul 20
27 min

The Learning Advantage: Pascal Finette on why learning speed is the only competitive edge that can't be copied

Today on You Might Try This, Cade and Stacey speak with Pascal Finette, author of Outlearn, about how organizations can accelerate learning by lowering the cost of failur

Jul 13
47 min

The Graceful Stumble: How to own what went wrong without letting it own you

Leadership isn't about avoiding mistakes, it's about what happens after you make one. In today’s episode, Stacey and Cade explore why the moments after a leadership stumb

Jul 6
30 min

The Authority Illusion: Why the leaders with the most influence often have the least formal power

Many new leaders assume that a title automatically gives them power, but they quickly discover that authority alone can only take them so far. In today’s episode, Stacey

Jun 29
31 min

The Chemistry Problem: Why stress and burnout aren’t mindset problems

Welcome back! In today’s episode, Stacey and Cade speak with executive coach and performance expert Jenny Evans about why stress and burnout are not just mindset proble

Jun 22
36 min

The Slow Drain: The early signals of burnout that high performers miss every time

Welcome back! In this episode, Cade and Stacey explore the hidden burnout signals that leaders and high performers often miss until it’s too late. Drawing on the origina

Jun 15
33 min

The Silence Tax: Why psychological safety isn't soft—it's the operating system your team runs on

Psychological safety shapes team performance more than talent alone. In this episode of You Might Try This, Stacey and Cade unpack the real meaning of psychological safet

Jun 8
34 min

The Pressure Decision: How to think clearly when the stakes are high and the clock is running

When the pressure is on and the clock is ticking, most leaders don’t rise to the level of their best thinking, they fall back on instinct. In this episode of You Might Tr

Jun 1
31 min

The Boss Equation: How to build the most important relationship in your career without losing your integrity

Managing up can feel uncomfortable, but avoiding it can quietly stall your career. In this episode of You Might Try This, hosts Stacey Philpot and Cade Cowan unpack why y

May 25
28 min

The Conflict Reflex: Why your default response to tension is working against you—and what to do instead.

Why do we still avoid difficult conversations, even when we know the cost? In this episode, Stacey Philpot and Cade Cowan explore the hidden reflexes driving conflict avo

May 18
29 min

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

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 c

May 11
28 min

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 abo

May 4
34 min

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, inclu

Apr 27
28 min

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

Apr 20
23 min

Chart trend

Position in the Management chart (US), last 90 days.

#33
all-time peak
4
days in the top 50 since Mar 2026

Chart positions

Where You Might Try This ranks today in each Apple Podcasts chart (US, Nov 1, 2026).

#159 ▼ 51 Management US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

Leaders need training. It’s not innate trait. A great podcast with fantastic lessons for all potential leaders.

Chris2206step · Mar 2026

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