2023 Chief of Staff job search strategy

Aspiring Chiefs of Staff, are you banging your head against the wall? Does this job search process look familiar?

1. You enter “Chief of Staff” into a job board.

2. You make a “reasonable” shortlist of 50 jobs.

3. You send out the same resume/cover letter.

4. You pray that you get a few interviews.

5. You wonder why you hear crickets.

It’s time to change your job search strategy. Unless you like getting rejected…

Read on for my full teardown to update your approach for 2023.

1/ Identify your ideal target boss, company and role.

Channel your inner Socrates and his Socratic method.

Ask yourself questions about your target boss’ leadership style, Zone of Genius, and personal values. Ask yourself about your target company’s size, capitalization, and culture while also examining risk factors. Then turn to the Chief of Staff job itself… ask yourself what you want to be doing in the role.

Reference my videos for the full set of questions here, here and here to get a full picture of your target boss, company and role.

2/ Optimize your LinkedIn profile to show off your best assets as a candidate.

Make sure that you're using a snappy tagline, have a modern profile pic and that your “Work Experience” and “About Me” sections pop off. Everything needs to be written in a way that stops a recruiter dead in their tracks to say, “I need to reach out to this person.”

Translation: you have to lead with your unique value proposition that puts you in the top 10% (ideally 1%) of candidates.

Cheat code: Watch my video here to create a memorable LinkedIn headline. Reference my newsletter here to optimize your LinkedIn profile.

3/ Create a shortlist of Chief of Staff jobs that fit your target boss, company, and role.

Read up on lots of JDs and do lots of sleuthing on LinkedIn. Create a shortlist of jobs that fit 80% of your criteria. Discard the jobs that don’t fit your target. Trust me, the smaller your shortlist is, the better. There’s a reason why it has the word “short” in it.

4/ Find people that work at companies on your shortlist and interact with them on LinkedIn.

Choose 30-35 people at those companies and split it across a 50%/30%/20% ratio of Directors, Recruiters, and Hiring Managers.

Interact with their content every day. Drop a like on their posts. Leave insightful comments as well. Remember to engage fully with everyone on a regular basis.

5/ Connect with a few folks in the DMs and then on Zoom.

After you’ve built a burgeoning relationship with these folks, send personalized connection requests. When they connect, send a thank you direct message (DM). In your message, request an informational interview.

In your interview, ask about an internal introduction to the hiring manager or recruiter. Be sure to ask for a referral.

Watch my video here to learn how to complete LinkedIn and cold email outreach.

6/ Connect with a recruiter during a first-round interview.

Land a 1st round interview and you're off to the races. Repeat the same strategy to get more interviews and to connect with people on LinkedIn.

In Sum…

Use LinkedIn as a free outreach tool to create new warm connections. That's the way that you're going to get in the door.

You're not going to have success competing against hundreds of other candidates out there that are also cold applying. Modify your strategy to break through the noise.

Chief of Staff Job Seekers Masterclass.

I’m building a community-powered course for aspiring Chiefs of Staff to land more interviews based on the coaching tips I listed above. This month I’ll publicly open up my Chief of Staff Job Seekers Masterclass on Circle.

It already exists. I’ve privately invited a small number of people in to get the party started… and if you’ve made it this far in the email, I want to give YOU the opportunity to join too.

Membership will be $200. But if you trust me enough to join sight-unseen, you can join for half price by replying to this email and saying you want to join (offer ends Monday March 12).

What you’ll get out of my Community-Powered Course:

1. Identify your ideal target CoS job

2. Make a plan to become an A+ CoS candidate

3. Create a unique story for your CoS candidacy

4. Update your resume, cover letter & LinkedIn

5. Define a LinkedIn outreach strategy

6. Receive feedback from your peers & from me

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