Season 2, Episode 9: Why Does It Feel So Wrong to Be a Leader?

Episode Description

We’ve all heard it: “Leadership is lonely.” But is it? And if it is, why do so many people still chase it?

In this episode of Why Does It Feel So Wrong to Be Human at Work?, hosts Pinaki Kathiari and Chris Lee explore the complex question of modern leadership—what motivates people to lead, what makes leadership feel “wrong,” and how our outdated assumptions about leadership may be holding us all back.

From Optimus Prime and parental wisdom to feedback fatigue and executive accountability, this conversation challenges traditional ideas and invites a more human-centered definition of leadership.

Together, they unpack:

• Why people pursue leadership (and what they’re not prepared for)
• The difference between ambition and accountability
• What real influence looks like—and why it often isn’t loud
• The cultural myths around “leadership material”
• Why empathy and emotional intelligence matter more than titles
• How to deal with change fatigue, feedback droughts, and the pressure to be perfect
• And what fictional kings, volleyball teams, and business visionaries can teach us about being a better boss

Timestamps

• 00:00 – Optimus Prime, Transformers, and the quest for good leadership
• 02:00 – What makes someone “leadership material”? (It’s not what you think)
• 05:00 – The perks vs. the pressure: Why leadership isn’t for everyone
• 07:00 – What studies say motivates people to lead
• 10:00 – Leaders as guardians of people’s lives—not just KPIs
• 12:00 – The weight of being both inspiring and accountable
• 14:00 – History of CEO behavior: From stability to crisis mode
• 17:00 – Trust, ownership, and letting go: What good leaders actually do
• 20:00 – Building diverse teams that don’t all think like you
• 23:00 – Redefining real leadership: Humanocracy and beyond
• 26:00 – Why feedback is vital—and why some leaders hide from it
• 28:00 – The toll of constant change on organizations and people
• 30:00 – Leaders, slow your roll: How too much innovation overwhelms teams
• 32:00 – Wisdom That Feels So Right: Books, tools, and personal stories

Wisdom That Feels So Right

• Good to Great by Jim Collins
• Humanocracy by Gary Hamel
• Reality-Based Leadership by Cy Wakeman
• Gallagher 2025 Workforce Trends Report (featuring change fatigue insights)
• Manager Tools – Practical leadership podcast and resources
• Transform Conference – Spring HR and leadership strategy event

Mic-Drop Moments

“When we win, it’s because of the team. When we lose, it’s on me.”

“Leadership isn’t about being the loudest voice—it’s about knowing when to listen.”

“Awesome resumes don’t make awesome leaders. Human ones do.”

Connect with Us

Pinaki Kathiari – LinkedIn | Local Wisdom

Chris Lee – LinkedIn | Gallagher Communication

Special Thanks

Cheers to Local Wisdom , they are spackle for communication teams. For 25 years they've filled talent and technology gaps for the top brands in the world while leading with heart and showing what leadership can really be. Thank you to our producer Brielle Saracini and our partners at SBX Productions for keeping our sound as sharp as our thinking.

Reflect + Share

What do you wish leaders understood better? What makes a leader worth following in your experience? We want to hear from you. Tag us, review the show, or send us your “WTF leadership” moments—and don’t forget to visit whydoesitfeelsowrong.com to bring these convos into your company.

Special thanks to digital communication agency Local Wisdom (www.localwisdom.com) for really believing in our mission and making this podcast possible. 

If this episode made you think differently, laugh, or even yell out loud, we want to hear about it! Connect with us on LinkedIn, and don’t forget to rate, review, and share – maybe with your work bestie… or even your boss if you're feeling bold.

We also bring these important conversations to conferences and private workshops, creating space for real, meaningful change. Take the first step at www.whydoesitfeelsowrong.com.

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