Kyle McDowell - Start with We: Leading without Ego

What does it really mean to lead with authenticity and move from “I” to “We” in today’s ever-evolving workplace? In this episode of Legendary Leaders, host Cathleen O’Sullivan is joined for a second time by Kyle McDowell, bestselling author of Begin With We, speaker, leadership coach, and former Fortune 10 executive. They talk about what’s changed since his book came out, how toxic cultures take hold, and why leading with principle matters more than ever.

Episode Timeline: 

1:38 Kyle’s mission: moving from “I” to “We” in leadership 

03:13 Cathleen invites listeners to reflect on their own leadership style and authenticity.

08:38 Kyle opens up about his long-standing experience with imposter syndrome.

12:16 The fine line between confidence and cockiness

15:31 Kyle shares his anti “fake it till you make it” stance 

18:26 The continued growth of Kyle’s book, Begin With We, and teases a second book.

23:03 The value of clear, jargon-free communication in leadership 

26:24 How empathy and practical advice guide Kyle’s evolution as a leader.

39:09 The challenges and impact of growing polarisation and toxicity in workplaces.

01:06:46 Kyle names his struggle with obsessing over details and how he balances strengths and weaknesses.

 

Key Takeaways:

• Real Leadership Starts with Principles: Kyle and Cathleen talk about what it really means to lead with values. For Kyle, it’s about shifting from “I” to “we” and living out a set of clear, practical principles.

• Toxic Cultures Can’t Always Be Fixed: They unpack what toxicity can look like, from one bad boss to a whole system. Kyle shares why it’s important to know when you can create change and when it’s time to walk away. 

• Doubt Happens, lead anyway: Both Cathleen and Kyle open up about imposter syndrome and how it shows up, even years into their careers. Kyle explains how he uses self-doubt as a check-in rather than a barrier. 

 

About Kyle McDowell:

Former Fortune 10 Executive turned inspirational speaker, bestselling author and leadership coach Kyle McDowell is on a quest to create cultures of excellence and reignite leaders’ passion and purpose. With nearly three decades of experience leading tens of thousands of employees at some of America’s biggest firms, McDowell’s philosophy is rooted in his trademarked principles, The 10 WEs. While today’s workforce is plagued with uncertainty and apathy, his strategy is simple - Begin With WE. McDowell’s mission is clear: crush the deep-rooted dysfunctions so many organizations passively accept. During his incredibly successful run in corporate America, McDowell’s leadership legacy was born from delivering superior results, empowering leaders, and driving massive cultural transformations. His Wall Street Journal and USA Today bestseller, Begin With WE, delves into the root causes of business dysfunction, offering a remedy through The 10 WEs framework. Rather than outsourcing solutions or ignoring cultural challenges, McDowell elevates leaders and sparks massive change within organizations by adopting a mindset that prioritizes

“WE” over “I,” “you,” or “me.” McDowell’s insights have earned him invitations to speak at prestigious business, educational, and nonprofit institutions, and his expertise has been featured in major national publications, including The Wall Street Journal, Forbes, and Inc. Magazine.

Connect with Kyle:

Instagram: www.instagram.com/kylemcdowellinc/

TikTok :www.tiktok.com/@kylemcdowellinc

YoutTube: www.youtube.com/@kylemcdowellinc

Facebook: www.facebook.com/KyleMcDowellInc

X: x.com/KyleMcDowellInc

LinkedIn: www.linkedin.com/in/kylemcdowellinc

Website: www.kylemcdowellinc.com

Connect: 
 

Find | Cathleen O’Sullivan 

Business: https://cathleenosullivan.com/