Clara Ma on the Common Threads of a Good Chief of Staff, Being a Generalist, and Building Trust

This conversation is a MUST listen for aspiring Chiefs of Staff or current Chiefs of Staff looking to further define their role!

Clara Ma is the Founder and CEO of Ask a Chief of Staff and has years of experience helping Chiefs of Staff and other Force Multipliers with career development, career planning, matching with the right leader, finding their next role, and much more.

Clara spent the first years of her career at a technical recruiting firm, placing engineer talent at early-stage startups like Warby Parker, Dollar Shave Club, and Bonobos. She then worked at AngelList helping startups hire technical talent and placing over 50+ candidates at other early-stage companies. Most recently, Clara has been cultivating a community of over 500 aspiring and current Chiefs of Staff through mentoring, providing resources, and finding their next opportunities for them.

During our conversation, Clara shared how she fell into the Chief of Staff role, what distinguishes the COS role from that of the EA or COO, and gives advice to anyone who may be considering the position or looking to grow in their role as Chief of Staff.


[0:00] About Clara Ma.

[2:38] About Ask a Chief of Staff.

[8:54] The main reason execs don’t hire a Chief of Staff—even though hiring a COS would help them with that problem.

[11:03] The common threads of a good Chief of Staff.

[14:28] The Chief of Staff role will continue to grow as the “generalist” career becomes an increasingly popular.

[19:01] The difference between an Executive Assistant and a Chief of Staff.

[22:45] A series A company requires a much different COS profile than a series D company.

[25:30] Educational vs experiential needs for a Chief of Staff.

[26:31] Claras journey as a Chief of Staff.

[42:08] How does one become a confident truth teller and strategic advisor to their principal?

[46:21] Why you need to do a monthly or quarterly reflection.

[47:21] The Chief of Staff role is the ultimate example of servant-leadership.

[48:02] Do you need any particular hard skills to be a Chief of Staff?

[51:42] The best place to learn about the Chief of Staff role is from people who are currently in the role.

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