Can you be too nice to lead?

In this episode, Michael Leibovich, GM and Head of Growth at Adobe, shares the career pivots, personal awakenings, and leadership lessons that shaped his unconventional journey from touring musician to executive. Michael opens up about getting fired, receiving feedback that questioned his approach to leadership, and learning how to balance empathy with outcomes. From scaling growth teams at Vimeo, Mindbody, AppFolio, and Abstract to navigating the emotional weight of letting someone go, Michael brings clarity to the messy, human side of leadership.

We explore how feedback becomes identity-shaping, what it means to truly “drive clarity” in a role, and why building a career is more about learning from missteps than chasing perfection.

In this conversation, you’ll learn:

• Why “you’re too nice” was the critique that stuck—and how Michael worked through it
• The surprising lesson a failed VP stint taught him about agency and self-worth
• A simple question that brings clarity to tough calls as a manager

Things to listen for:

(00:00 ) Intro

(01:24 ) Growing up in an artistic blue-collar SoCal home

(02:30 ) First jobs and career aspirations

(04:29 ) Journey into music and touring

(05:44 ) Transitioning to tech and SaaS

(07:24 ) How being in a band helped in learning business

(11:02 ) Thank you to our sponsor, ThriveStack

(12:20 ) Being too nice as a leader and finding a balance

(21:27 ) Paying impactful feedback forward

(23:38 ) Navigating imposter syndrome

(26:46 ) Leadership challenges and job insecurity

(29:27 ) Reflecting on career transitions

(31:45 ) A costly mistake and learning experience

(36:17 ) Managing team dynamics as a leader

(44:42 ) A useful shift in perspective

(46:46 ) Driving clarity and embracing intuition

A huge thanks to this episode’s sponsor:

ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/

Resources:

Connect with Michael:

LinkedIn: https://www.linkedin.com/in/michaelleibovich/

Adobe: https://www.adobe.com

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching