"My Manager Doesn't Understand Me... Help!"

About this episode

The episode discusses how to improve communication and understanding between an employee and their manager.

Have you ever felt misunderstood by a manager? If so, you know how frustrating—and downright demoralizing—it can be. Today’s caller, Mike, is stuck in that very situation. His manager constantly second-guesses his work, and Mike is desperate to find a way to get on the same page. To tackle this challenge, Jason is joined by Jenny Wood, former Google executive and author, to break it all down. Together, they equip Mike with a clear, actionable framework to transform his next conversation with his manager—turning tension into trust and frustration into forward momentum. Buy Jenny's book Wild Courage ⁠here⁠!

People in this episode

Host: Jason

Guest: Jenny Wood

Topics covered

• manager relationships
• communication
• workplace frustration
• trust building
• career advice

Keywords

• manager misunderstanding
• workplace communication
• employee advice
• trust in management
• career development

Mentioned in this episode

Organizations: Google

Books & works: Wild Courage

More episodes of Help Wanted

• Why Asking for Help Makes Relationships Stronger · June 11, 2026 · 13 min
• How To Turn Cold Outreach Into a Lasting Network · June 9, 2026 · 37 min
• Handle Awkward Conversations Like a Pro · June 4, 2026 · 11 min
• Why You Should Network Like Goldilocks · June 2, 2026 · 25 min
• Inside Pitching Shark Tank and How Old School Businesses Win in an AI-Powered World with Sabin Lomac · May 28, 2026 · 51 min
• "I'm Not Popular At Work— Will That Affect My Growth? Help!" · May 26, 2026 · 37 min