Emily Sander talks about how Chiefs of Staff often feel guilty or frustrated about things like not working long enough hours or not helping a struggling teammate. She explains that being too empathetic or self-critical can backfire and suggests telling yourself, "and that's okay," to relieve pressure and keep perspective. Real examples include feeling called out for working from home or regretting not helping someone in a team meeting.

Get in touch with Emily:
Feeling the pressure to do more, be more, or fix everything? Book a clarity call w/ Emily here.

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Who Am I?
If we haven’t met 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:
00:25 Common Chief of Staff Struggles

01:04 When Empathy Becomes a Detriment

04:16 The Power of Saying It's Okay

06:17 Mountains Out of Molehills

08:03 Building a Higher Baseline

09:00 Try This Exercise

Emily Sander talks with Lindsey Gardner, a multi-time Chief of Staff and co-founder of Sapphire Chief of Staff, about balancing people and business priorities. Lindsey Gardner shares lessons from working with the same CEO for a decade, why she always puts people first, and how clear communication builds trust. She also explains Sapphire’s approach to Chief of Staff recruiting and development and discusses how AI should be seen as a tool—not a replacement for humans.

Links Mentioned:
Sapphire Chief of Staff Website

Connect with Lindsey Gardner on LinkedIn

Get in touch with Emily:
Want to chat with Emily? Book a quick clarity call here.

Free Leadership Resources

LinkedIn

Website

Newsletter

Who Am I?
If we haven’t met 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:
02:00 Selling the Chief of Staff Role

04:08 A Decade With One CEO

10:05 People First vs Numbers

13:45 Kindness vs Niceness

17:46 AI and Company Stage

21:45 Hard Tradeoffs in Practice

28:38 Sapphire Chief of Staff Wrap

Emily Sander answers a listener question from Sarah in Charlotte, a Chief of Staff handling board governance, leadership meetings, and benefits rollout. The episode covers how to build strategic relationships with the board, use back channels professionally, and avoid being seen only as admin support while keeping the founder focused and the team aligned. Real examples include collaborating with consultants and prepping the chairman for meetings.

Get in touch with Emily:
Want help building stronger board and executive relationships? Book a clarity call w/ Emily here.

Free Leadership Resources

LinkedIn

Website

Newsletter

Who Am I?
If we haven’t met 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:
00:25 Listener Question Setup

01:20 Sarah’s Challenge

03:00 Leverage Board Access

05:20 Build Allies and Backchannels

08:03 Talk Strategy Not Admin

10:30 Coach the Board on Focus

13:15 When Founders Spiral

16:07 Create More Board Touchpoints

17:48 Wrap Up and Next Steps