10 Chief of Staff hiring mistakes

Avoid the risk of a bad hire

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Hello, and welcome to the Office of the CEO newsletter! I’m Mackenzie, and I write about all things Chief of Staff, Executive Operations and the CEO Office.

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Hiring a Chief of Staff? Avoid these 10 mistakes.

CEOs, top executives and hiring managers, listen up! The Chief of Staff is a highly specialized role and it’s tricky to get right. A bad hire will cost you dearly.

Trying to unwind a Chief of Staff and find their replacement is a tortuous path. Experts say the cost can amount to 213% of their salary.

Reduce the risk of a bad hire by NOT making the following mistakes:

1/ You don’t take time to properly assess your leadership needs

If you don’t know what your CEO and C-suite teams needs, stay away from hiring a Chief of Staff for now. Don’t act on a whim to hire a Chief of Staff. Figure out what you really need.

2/ You don’t understand the art of the possible with a Chief of Staff

Many CEOs and hiring managers don’t know the full impact that a Chief of Staff can bring. Take a look at my Chief of Staff playbook here for a full review of the impact this new team member can bring to the CEO, C-suite and entire organization.

3/ You don’t define the Chief of Staff role clearly enough

I’ve seen too many hiring managers control-C and control-V another company’s Chief of Staff job description. It’s lazy AND dangerous. Take some time to craft the exact roles and responsibilities.

4/ You don’t equip the Chief of Staff with an Executive Assistant

Your Chief of Staff needs to be free to focus on strategic, high priority matters. Make sure you hire an Executive Assistant who can take on the usual calendar, travel and admin responsibilities as well as any overflow work from the Chief of Staff.

5/ You don’t look for a diverse set of candidates

McKinsey, Bain, and BCG plus HBS, GSB, and Wharton aren’t the only sources for top candidates. And be sure to look internally as well as externally to find your next Chief of Staff.

6/ You don’t use social media to reach top candidates

Top candidates are highly LinkedIn savvy and can appreciate a note direct from your CEO. Make sure to leverage the power of the social network to attract the best candidates.

7/ You aren’t candid about your company’s flaws

Chiefs of Staff need to go eyes-wide-open into a new role, and better yet be super excited about all of the problems. The best candidates will reframe them as growth opportunities for themselves and the company.

8/ You don’t use a standardized scorecard for evaluating candidates

The Chief of Staff hiring process should be no different than another C-suite hire - it’s extremely high stakes. Make sure to use the same scorecard for each Chief of Staff candidate.

9/ You don’t include a project in the interview process

The CEO - Chief of Staff relationship is considered THE most intimate in the industry. You need to get a flavor of what it’s like to work with your future Chief of Staff. Make sure you assign a project, better yet compensate candidates for their work, even if you don’t hire them.

10/ You don’t close your candidates fast enough

Top candidates will get swooped up by other employers. You must act fast to get your top pick.

So there you have it, the top 10 no-no’s when hiring a Chief of Staff.

Share this with someone who is thinking of hiring a Chief of Staff or is in the middle of the hiring process right now.

And feel free to reach out if you need help recruiting your next Chief of Staff.

You’re Invited! Spring Happy Hours

Office of the CEO Happy Hour series, presented by Mackenzie and the Cedar team.

​I'm excited to host spring happy hours for my Office of the CEO community in San Francisco (April 4, RSVP), Palo Alto (April 8, RSVP) and New York (May 2, RSVP). Join us!

One of my goals this year is to host unique offline events to unite my online Executive Operations community.

This includes 1,000s of folks from my LinkedIn audience, Beehiiv newsletter, and readers of my recently published Chief of Staff playbook.

Who should attend? ​Founders, CEOs, Executive Assistants, Chiefs of Staff, aspiring Chiefs of Staff, Executive Communications professionals and Executive Operations professionals are all welcome.

​Why come to my happy hour? ​You’ll of course be able to network with like-minded Office of the CEO professionals. But also it wouldn’t be a Cedar event without some sort of thought provoking and entertaining programming from my team. And as an amateur chef, you may even get a little take home gift from me. See you there!

Secure your spot: San Francisco (April 4 RSVP), Palo Alto (April 8 RSVP) and New York (May 2 RSVP)

Share this event with a friend or colleague who also would be interested in joining.

Upcoming Events

Webinar: Chapter 1: Chief of Staff 101 from The Chief of Staff Playbook, 2nd Edition, Cedar, LinkedIn Live/Zoom, March 27, 2024, 8am / 11am PT / 3p GMT. RSVP here.

Don’t forget to register for our webinar next week! Join 50+ others.

Happy Hour: Office of the CEO 2024 Spring Happy Hours, Cedar, IRL. RSVP for SF (4/4) here, Palo Alto (4/8) here and NYC (5/2) here.

Join us for our upcoming happy hours. We’d love to see you.

Panel: Mastering Stakeholder Management and Making a Lasting Impact, Women in the COO Community, Armstrong Wolfe, New York City, NY, April 24, 2024 (Private Event)

Send me a note if you’re interested in booking me as a niche, unique speaker at your next event to speak about the Chief of Staff, Executive Operations and/or the Office of the CEO.

Chief of Staff Jobs

Welcome to our Chief of Staff job board. If you have a Chief of Staff job you’d like shared to 2,000+ readers of this newsletter or need hands-on recruiting help to hire your Chief of Staff, reply to this email.

Chief of Staff to the CTO, WorldQuant, Austin, TX, Finance, Corporate

Chief of Staff, Ohmium, Fremont, CA, Startup

Chief of Staff, TEK Systems, Los Angeles, CA, Tech, Corporate

Chief of Staff, City of Seattle, Seattle, WA, Government

Chief of Staff, Rex, Austin, TX, Tech, Startup

Chief of Staff, Glocap, New York, NY, Finance, Corporate

VP, Chief of Staff, Moody’s, New York, NY, Finance, Corporate

Help Us Grow

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Thanks for reading! Stay tuned for next week’s edition.

Until next week,

Mackenzie

Mackenzie Lee | Founder & CEO
M: 650.283.4152 | E: [email protected]
New York City, NY
www.CedarChief.com

At Cedar, we turn executives into fast and fearless leaders.

Thanks to technology, changing markets, and demanding investors, the C-suite job is tougher than ever. We help executives find freedom from blockers and busywork.

Our mission is to help 1 million CEOs and their C-suite teams let go and do more of the things that matter. We help you hire a Chief of Staff, build an Office of the CEO, and implement C-suite operating systems.

On average our clients see a 25% meeting reduction, 20% strategic sales increase, and 2x speed-to-execution in their first 90 days with us. Data is continuously analyzed to improve performance and accelerate growth.

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