Hello and welcome to the 51 new readers of the Office of the CEO newsletter! I’m Mackenzie, and I write about all things Chief of Staff, Executive Operations and the CEO Office.

Every week, you’ll get 1 new leadership tip or tactic that you can implement, a roundup of our exclusive Office of the CEO events, a list of hot Chief of Staff jobs, and more.

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PS Join me and 100s others at our upcoming events: How to Hire a Chief of Staff Webinar, NYC Happy Hour, and more.

10 Chief of Staff Hiring Mistakes

Hiring a Chief of Staff? Avoid these top 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 and trying to unwind a Chief of Staff from a company is a tortuous path. Experts say the damage 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

The best leaders have an acute sense of their Zone of Genius and conversely, their Zone of Incompetence. They understand what tasks drain their energy and time, which ultimately they should delegate to their future Chief of Staff. Take time to do a proper assessment of yourself and your leadership team to define leadership gaps.

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

CEOs and top executives that have never had a Chief of Staff before lack the understanding of the art of the possible with this role. Avoid leaving value on the table: learn about successful Chief of Staffs and Offices of the CEO. Talk to others in your network who have one and read up on relevant literature, like The Chief of Staff Playbook, 2nd Edition.

3/ You don’t define the role clearly enough

Don’t control C and control V a Chief of Staff job description that you found online. You want to properly tailor the role based on the leadership assessment you made and your unique leadership needs. Think: what areas do you need enablement to increase your impact at the C-suite level?

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

Avoid hiring a Chief of Staff without an Executive Assistant in place or a plan to hire one in the near future. Your Chief of Staff cannot fully deliver high impact leadership without the proper support. Get an Executive Assistant.

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

Chiefs of Staff come in all shapes and sizes. The best hiring managers present diverse sets of candidates that present a range of experiences, domain knowledge, and ideas. Make sure that you go beyond the traditional consulting and MBA profile to consider non-traditional backgrounds.

6/ You don’t have a standardized scorecard for evaluating candidates

Assessing Chief of Staff candidates should be consistent across all potential hires. You must use a scorecard to ensure even evaluation by the hiring panel. DM me if you want a copy of my scorecard.

7/ You don’t include a project or work samples in the interview process

Talk interviews are inherently biased and bad at predicting future results. Reduce the risk of a bad hire by requesting work samples or even including a short project as part of the interview process. Even better, compensate candidates’ project work so that they feel that you are invested in the process and aren’t stealing their ideas.

8/ You aren’t candid about the flaws

Let’s face it, you are hiring a Chief of Staff because something is NOT working out for the leadership team, and by extension the company. Don’t say that the opportunity is all sunshine and rainbows. Frame this role as an opportunity to radically change the trajectory of the leadership team, for the better.

9/ You don’t use social media to reach candidates

Great candidates are responsive to social media outreach because they can see social proof from the hiring manager and also their future boss, the CEO. They can get a sense of company culture through the profiles and content that you put out on LinkedIn, X and Instagram. Make sure to incorporate social into your recruiting strategy.

10/ You’re slow to react to candidates in the interview process

Speed is the name of the game. You must act quickly and decisively to get A Player talent, otherwise they’ll move on before you know it. That means you have to keep in constant contact with candidates and make fast decisions en route to hiring your Chief of Staff.

And that’s it, the 10 mistakes to avoid when hiring your Chief of Staff.

Want to learn how to properly hire your Chief of Staff? RSVP to the webinar below on How to Hire a Chief of Staff from Chapter 2 of The Chief of Staff Playbook, 2nd Edition.

Join me for a Cedar webinar on How to Hire a Chief of Staff

Next Thursday April 12 at 12p ET / 9am PT / 4p GMT. Register here.

Join my how-to-recruit-your-right-hand webinar where I cover Chapter 2: Chief of Staff Search from The Chief of Staff Playbook, 2nd Edition.

Who’s Invited?

-Founders & CEOs who want an end-to-end guide to hiring their Chief of Staff
-Chief of Staff job seekers curious to learn how CEOs run a search
-COOs, CHROs, and leaders who need to hire a Chief of Staff for their CEO
-Recruiters new to the Chief of Staff role and don’t know where to start
-Investors & board members whose CEOs could benefit from a Chief of Staff

Webinar Details

Welcome to a series of webinars dedicated to the newly published The Chief of Staff Playbook, 2nd Edition. We’ll cover 9 chapters of content in greater detail, while engaging in more intimate conversations with our audience.

Join me and the Cedar team on Thursday April 18, 2024 at 12pm ET / 9am PT/4p GMT for our second webinar in the series. We’ll cover Chapter 2 of The Chief of Staff Playbook, 2nd Edition: Chief of Staff Search: How do you hire an exceptional Chief of Staff?

RSVP and share this event with your network. This event will be recorded if you can’t make it.

We’ll kick off the webinar with a 10-step guide to hiring a Chief of Staff in today’s hectic job market. We’ll cover common Chief of Staff hiring mistakes (hint: your CEO shouldn’t be running the search) and show you the background you should be looking for in your next Chief of Staff.

Then, we’ll cover how to build your customized Chief of Staff profile and the alternative titles you should consider for the role. We’ll go through the hard and soft skills a Chief of Staff needs. And we’ll end with our Chief of Staff interview scorecard - a helpful tool you can take with you to kick off your search. Questions from the audience to follow.

Register now. See you there!

Upcoming Events

Workshop: Turn Your Executive Team into Fast and Fearless Leaders: How to Build an Executive Operations Function Engineered for Speed, EA Ignite, American Society for Administrative Professionals, Nashville, TN, April 23, 2024 (Sold Out)

Roundtable: Become a Fast and Fearless Leader in the Office of the CEO (or Any Executive Office), EA Ignite, American Society for Administrative Professionals, Nashville, TN, April 23, 2024 (Sold Out)

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). Reply to this email if you are a woman in financial services and you’d like to attend.

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, Founder’s Studio, Bain, Remote, Tech, Corporate

Chief of Staff and Strategy, Uncommon Schools, New York, NY, Non-Profit

Senior Director, Chief of Staff, Field Operations, Okta, San Francisco, CA, Tech, Corporate

Chief of Staff to CCMO, Freshworks, Bellvue, WA, Tech, Corporate

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

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

Chief of Staff (GTM), Monta, Miami, FL, Tech, Startup

Help Us Grow

Our mission is to impact 1,000,000 leaders. If this newsletter would help someone in your network learn more about how to avoid hiring the wrong Chief of Staff candidate, please forward it to them.

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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.