Lessons from a Long-Term Chief of Staff Partnership

An 18-year partnership between Jennifer Baron and her CEO, Justin, shows what makes a chief of staff role work over the long term. It was not planned from the start. It grew from trust, honesty, and shared effort. And it shows how one strong partnership can shape a career and a business.

Key Takeaways

  • Failure can open the right door
    Jennifer lost her job during the financial crisis. That setback led her to a temp role where she met Justin. That temp job became her long-term career.

  • Trust is built through small actions
    She did what she said she would do. She delivered work quickly and correctly. That consistency made Justin rely on her more and more.

  • A chief of staff must be honest, even when it is hard
    Jennifer learned to speak up and give feedback. She became someone who could say things others would not say.

Notable Quotes

  1. “We basically agreed to merge our careers together and keep working with each other as long as it was a positive partnership.”

  2. “One of my roles is being Justin’s truth teller. I’m going to tell him things that other people might not say.”

  3. “Relationships are the secret sauce for a team, whether you’ve got two people or 200 people.”

Real-World Applications

  1. Turn setbacks into new paths
    Example: If you lose a job, take roles that build skills and connections. A short-term contract could lead to a long-term career.

  2. Build trust through reliability
    Example: Deliver projects on time and communicate clearly. Leaders trust people who follow through.

  3. Invest in the working relationship
    Example: Learn how your leader thinks. Understand their strengths and weaknesses. Support them in ways that make them more effective.

This partnership worked because both people showed up fully. Jennifer earned trust through action. Justin gave her space to grow. And over time, their relationship became the backbone of their success.

 
 

Time Stamps:

00:31 Discovering Family History

01:54 Jennifer's Career Beginnings

03:43 Meeting Justin and Early Career at Endeavor

05:23 Becoming Chief of Staff

10:03 Private Equity and Company Growth

16:30 Current Role and Responsibilities

19:08 Role of a Chief of Staff in PE Firms

20:43 Building Trust and Dependability

24:44 Evolving Together Over 18 Years

27:41 Adventures in Scotland: A Team-Building Experience

30:55 Advice for Aspiring Chiefs of Staff

Links Mentioned:

 

About The Author

Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense. 

Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.

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