Listener Question: How to Handle a Boss Who Won’t Listen

Leveraging Leadership

Emily answers a question from someone struggling to work with a new boss at a family-owned business who ignores process, oversells services, and doesn't value their input. She shares practical advice on "increment training"—giving the boss positive feedback for following the right process and building small wins over time. Emily tells her own story about working with a difficult, charismatic sales leader and highlights the importance of meeting halfway, using patience, and looking for ways to turn friction into teamwork.

Links Mentioned:

• Email Emily for your questions
• Message her on LinkedIn
• Clarity Call with Emily

Free Resources:

• Strategic Planning Checklist
• Chief of Staff Skills Assessment Checklist
• A Day in the Life of a Chief of Staff
• Chief of Staff Toolkit

Get in Touch With Emily:

• Connect on LinkedIn
• Follow on YouTube
• Learn more about coaching
• Sign up for the newsletter
• Clarity Call with Emily

Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:

01:11 Challenges with the New Boss
02:38 Possible Reasons for the Boss's Behavior
06:12 Training the Boss Incrementally
07:27 Personal Story: Handling a Similar Situation
13:53 Conclusion and Final Advice

Chapters

1. Listener Question: How to Handle a Boss Who Won’t Listen (00:00:00)

2. Challenges with the New Boss (00:01:11)

3. Possible Reasons for the Boss's Behavior (00:02:38)

4. Training the Boss Incrementally (00:06:12)

5. Personal Story: Handling a Similar Situation (00:07:27)

6. Conclusion and Final Advice (00:13:53)