209: Middle Management Is Broken...Here’s What Actually Works | Angie Callen

In this powerful episode of The Learn-It-All Podcast, host Damon Lembi digs in with executive coach and Career Benders founder, Angie Callen to reveal why authenticity is a performance tool, how generational dynamics shape workplace trust, and what you—and every leader—can do to rally a motivated, loyal, and thriving team. 

Discover Angie's journey from civil engineering to entrepreneur, her best practices for individual growth plans, and the key conversations every manager should have with their team. From perfectionism and the myth of work-life balance to actionable tools like values exercises and curiosity-driven reflection, this episode is packed with ideas for anyone ready to take ownership of their career and lead with purpose. 

In this episode, you’ll learn: 

• The real reasons employees leave: How generational values and management misalignment fuel the leadership gap. 
• Why authenticity isn’t just a buzzword—and how to leverage it to build trust and team engagement. 
• How self-awareness, journaling, and curiosity can help you find passion and purpose at work. 
• Tips for managing and motivating different team members as individuals, not units. 
• Strategies for middle managers faced with culture clash and organizational resistance. 
• Why executive presence, confidence, and self-reflection are critical in the modern workplace. 

Timestamps: 

00:00 – Why teams aren't motivated by the same things 

01:11 – Study: 64% of employees trust robots more than managers 

02:02 – The generational gap in leadership and communication styles 

03:52 – Why authenticity matters in leadership 

06:41 – Angie's career path: from engineer to entrepreneur 

08:26 – From art galleries to coaching—embracing “career tumbleweed” 

11:32 – Why most people never find passion in their work (and how to start) 

13:20 – Taking ownership of your career trajectory 

14:04 – Tips for small, low-risk career pivots 

15:30 – Using journaling and reflection to clarify your strengths 

17:14 – The leader’s responsibility: motivating and developing teams individually 

19:38 – Simple exercises to get to know your team faster 

23:49 – Coaching frustrated middle managers: tackling organizational roadblocks 

26:32 – The biggest current challenges for today’s leaders 

28:56 – Building confidence through coaching (and why it matters) 

33:48 – Why AI can’t replace human-to-human coaching 

34:05 – How Angie’s coaching style has evolved 

37:58 – Angie’s ideal clients—and her unique coaching philosophy 

41:02 – Must-have free resources for stuck middle managers 

42:05 – Final advice: You have more control over your career than you think 

 

About Angie Callen 

Angie Callen is a former civil engineer turned executive coach, podcast host, and the founder of Career Benders. With a colorful journey spanning engineering, nonprofit leadership, entrepreneurship, and career coaching, Angie specializes in helping professionals—especially technical leaders—find their authentic path and unlock their leadership potential. Her coaching focuses on self-awareness, confidence, and finding purposeful, aligned work. Angie is known for practical, people-first strategies that inspire growth and real results. 

Resources & Mentions: 

• Career Benders Free Resources – Core Values exercise and other tools mentioned by...