How to Have Difficult Conversations at Work When It's Your Friend

Your friend helped you land a vendor. Now your company wants to end the contract, and you get to deliver the news. Who's talking, the friend or the person doing her job?

Fresh from the Women of Pavilion summit in New York City, Heather and Blakely revisit the sticky situations women brought into the room. Rachel Johnson, founder of MoJo Marketing and co-lead of Women of Pavilion, joins them to share the answers she couldn't give while moderating their session.

They tackle a coworker who thinks women should stay home, a promotion double standard, the pressure to learn AI, and a team that's afraid of the person trying to turn things around. Blakely also revisits her answer about AI and explains why she needed to consider the pressure facing women still in the workplace.

Key Takeaways:

• Set boundaries with a dismissive coworker.

• Deliver bad news without losing a friendship.

• Ask for clear promotion criteria.

• Speak up for women who aren't in the room.

• Build AI skills without outsourcing your judgment.

• Name the problem while protecting confidential details.

• Check on the person holding everything together.

  
  

Please consider sharing this episode and subscribing to the show for more of the career questions women want answered but rarely ask out loud.

Follow Our Guest:

• Rachel Johnson on LinkedIn: https://www.linkedin.com/in/rachel-m-johnson/ 

• MoJo Marketing: https://mymojomarketing.com/ 

  
  

Follow Not All Business:

• Instagram: https://www.instagram.com/notallbiz/ 

• LinkedIn: https://www.linkedin.com/company/notallbusiness/ 

• Substack: https://notallbusiness.substack.com/ 

  
  

Links & Mentions:

• Pavilion: https://www.joinpavilion.com/ 

• Women of Pavilion: https://community.joinpavilion.com/topics/28813/page/info 

• Conversation with Dr. Amy Diehl, author of Glass Walls: https://community.joinpavilion.com/networks/events/292979 

• Pavilion Women's Summit playlist: https://open.spotify.com/playlist/3wshSFNsQTWyMIfoEbaypL?si=LJcAzXPJSY-ue-Dj74F2kQ 

• Women in the Workplace 2025, McKinsey and LeanIn.Org research on promotion gaps: https://www.mckinsey.com/featured-insights/diversity-and-inclusion/women-in-the-workplace 

• Keith Harkin, the musician Heather & Blakely met in the airport lounge: https://www.keithharkin.com/ 

• Melissa Moody, the give and the get: https://www.linkedin.com/in/melissammoody 

• Ginger Graham, whose advice to name the problem helps teams understand what's happening: https://gingerandbaker.com/who-we-are/ 

• Swati Paliwal, the ReSO AI founder who led with what she could give before making her ask: https://www.linkedin.com/in/swatipaliwal1/ 

• ReSO AI, Swati's company helping brands get discovered in AI search: https://www.linkedin.com/company/resollm-ai/ 

  
  

Submit Your Sticky Situations:

• Got a sticky situation for Not All Business? Send an email or voice recording to sticky@notallbusiness.com or drop your question in the comments.

  
  

Thank You to Our Sponsors:

• Face Five Acne Clinic, Root-Cause Acne Care, No Harsh Prescriptions Required: https://facefiveacne.com/  - code NOTALLBIZ10 for 10% off your first order

• Follow Face Five Skincare: https://www.instagram.com/facefiveskincare/ 

• Follow Wellness with Yuki: https://www.instagram.com/wellnesswithyuki/ 

  
  

Not All Business is Sex Ed for Your Career: the honest work questions women want answered but rarely ask out loud. Hosted by Heather Cooper and Blakely Graham, alongside producer and co-host Clay Carnill, new episodes drop every Thursday covering the real stuff: workplace drama, salary negotiation, imposter syndrome, and the sticky situations nobody has a script for. Subscribe so you never miss the next conversation.