Issue 18: Landing a Chief of Staff Role in Today's Market
If I was in the market for a Chief of Staff role right now, this what I would do.
Welcome back, aspiring and current Chiefs of Staff!
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How can you get a Chief of Staff role in today’s job market?
In the very first issue of this newsletter, I talked about four ways you can land a Chief of Staff role.
But Clara, you say:
My company isn’t interested in having a Chief of Staff,
Every LinkedIn posting I see for a Chief of Staff job has 200+ applicants within 2 hours,
I did all the things you said in my last newsletter and I still don’t have a Chief of Staff job,
In this week’s issue, I’m going to give you some tactical ways to increase your odds of landing your next Chief of Staff role. These tips are based on my experiences recruiting for the role, how I would approach my job search if I were actively looking now, and the advice I’ve given to many Chief of Staff hopefuls in the last 6 months.
The difficult news is: Let’s just start by saying, the job market is bonkers right now - the Chief of Staff job market especially so:
1️⃣ There are more people looking for jobs now compared to before.
2️⃣ There are more people looking for Chief of Staff jobs now compared to before.
The good news is: There are more companies hiring for Chiefs of Staff now compared to before too! Even three years ago when I was on the search for a Chief of Staff role, they were far and few in between - not to mention, many Chief of Staff roles aren’t listed (more on that later).
💪🏼 Evaluate your own strengths and weaknesses
Time and time again, this is my first piece of advice when it comes to beginning your Chief of Staff job search. And even if you’ve been searching for a while, I still recommend you do this exercise to re-evaluate your priorities and skill sets.
Being an effective Chief of Staff requires a level of self awareness unlike any other role. In Issue 16 of this newsletter, I talk about figuring out your “blindspot matrix.” Figure out what you uniquely know and understand and what you have yet to learn. Reflect on things that can be taught in the next job and things you can learn on your own while you search.
Your next step is to make a few lists. From
’s newsletter, she suggests making four lists:From these lists, you’ll be able to:
1️⃣ Learn what you are uniquely good at and what makes you happy
2️⃣ Use what you know to find the roles that are uniquely suited to you
Which leads us directly into our next step:
🔦 Get Narrow and Focused
At the start of every conversation, when I talk to aspiring Chiefs of Staff, I ask them what industries and company sizes they’re interested in. Too much of the time, the response I get back is “Anything. I’m open to all industries and all sizes of companies.” Imagine if we had that same response when asked “What are we looking for in a partner?” As much as we think just narrowing down the role to “Chief of Staff” is sufficient enough, it isn’t. There are nuances and differences between being a Series A Chief of Staff and an S&P 500 Chief of Staff. The same person will likely not be successful in both environments.
Though it might feel like you’re narrowing your possibilities by committing to a more specific set of requirements for your next role (e.g. “I would like to be a Chief of Staff at a Series A, Climate focused company”), the benefit to doing this intentional narrowing is multi-fold:
1️⃣ Your list of applications becomes much shorter and you are able to narrow your focus and apply only to roles that truly interest you. As a result, the quality of your applications will go up.
2️⃣ You get clear on the kind of Chief of Staff you want to be and studies have shown that “conjuring your future possible self” helps you take more intentional (as well as subconscious) action towards being that version of self.
3️⃣ You will refine your talking points and “career story” better when you’re clear on the role you’re looking to take on. You should be able to clearly articulate in 3-5 sentences why you are interested in being this type of Chief of Staff at this type of company. Keep it concise, pithy, and tight.
4️⃣ You will also know how to guide and steer your networking in a way that is much more focused as opposed to “spray and pray.” More on this in “Activate your network in the right ways” below ⬇️
🕰️ The 2-Hour Job Search
I was recently turned on to this resource by an aspiring Chief of Staff and it encapsulates so much of how a “modern job search” should be run. As many of you already know, the “traditional” ways of applying to a job, especially a Chief of Staff role, are wholly unhelpful. Chief of Staff job postings have over 200 applicants in two hours and truth be told, I’m wary that someone is combing through all the resumes given how strapped most companies are for time and resources at the moment.
The 2-Hour Job Search, by Steve Dalton, program director and senior career consultant at Duke University's Fuqua School of Business, teaches job seekers to do this:
1️⃣ Develop a target list of companies (“The LAMP List”),
2️⃣ Identify and connect with people at those target companies (“Contact”), and
3️⃣ Use informational conversations to convert these contacts into advocates who will ultimately refer you (“Convince”).
No need to read the whole book if you want to get right into the action items; there are great summaries such a this LinkedIn post and UVA Darden’s Career Services post.
Additional tactics I would add to the 2-Hour Job Search methodology are:
✅ Use Bridge to more easily request intros - if you want an invitation to this app, reply to this email or leave a comment on this issue and I’d be more than happy to add you to my network.
✅ Have your intro email ready to go. This is my favorite forwardable template and you want to make it as easy as possible for the folks who are helping intro you. The easier it is for them, the more quality emails you’ll get out there.
➡️ I would also additionally download a clipboard manager, such as Paste, to keep your baseline templates on hand.
✅ Don’t limit your contacts to just alumni from your school. Use contacts from communities you’ve joined, past companies you've worked at, 2nd degree connections, etc.
My favorite “Final Tip” from this summary:
Job searching is a numbers game 🔢. The more referrals you have and the more no's you get, the closer you are to a job.
But keep in mind, you want meaningful numbers. Not random job applications.
🎤 Informational Interviews
Once you land intros, get smart about conducting “informational interviews.” I often get many requests for folks to “pick my brain” about being a Chief of Staff. While I will engage in some of these conversations if they’re coming at the bequest of a close contact, I’m often cautious about taking too many of these types of calls because the agenda is unclear.
In order for an informational interview to serve its most effective purpose, both parties have to come prepared. The interviewer should be clear in their intentions about what they want answers to, and the person being interviewed should be clear about what what information would be most productive to bring to the conversation.
In my mind, there are two types of informational interviews you should be aiming for:
1️⃣ People currently or formerly working for the company you hope to work at:
In these calls, you should be asking questions about the company and what they look for in a candidate. The goal of these calls isn’t to fish for a job, but to better understand what can make you a standout candidate. Get clear about the company culture and values, and then map them against what you’re looking for. You can wrap up the conversation by letting your contact you know that you’d be interested in working for the company and your specific skills that you bring to the table. Ask for any advice they’re willing to give about making yourself a stronger candidate, follow the advice, and then follow up to report back on how those actions panned out. It also never hurts to buy the person a coffee (in person or virtual) to thank them for their time ☕️
2️⃣ People who have the job you are aiming for:
In these calls, you’re seeking patterns. Again, using the specific role as guidance, look for people who have the job you’re looking to land. Ask questions about how they came into the role, what skill sets were transferable from previous roles, and what advice they would give to someone in your position who is looking to follow in their footsteps. If you have really great chemistry with them, consider asking them to be a mentor.
Informational interviews accomplish two things: you’re getting more information on how to be a better candidate for the roles you’re interested in, and you’re making yourself top of mind when openings for new roles arise. It’s happened before where a current Chief of Staff is actually looking for their replacement and the right timed conversation has led to a Chief of Staff role that was never even posted. Remember what I said earlier about some Chief of Staff roles not even being listed?
🤝🏼 Activate your network in the right ways
In prior issue, I talked about building your LinkedIn brand. Building your brand includes expanding and activating your network in the right ways. With LinkedIn in particular, you have the ability to better tailor your feed to surface more positions that meet your criteria. On a weekly (if not daily) basis, you should be connecting with folks that have your dream role and people who talk about topics adjacent to your dream role. Again, using the “Series A Climate related Chief of Staff” archetype as an example, you should be connecting with folks who are either “Series A Climate Chiefs of Staff” and/or “people who have founded companies and/or are thought leaders in the space.”
When connecting, I like including a short message to give people an idea of why you’re reaching out. Make it easy for folks to connect the dots and understand how you might fit into their network.
Hi [FIRST NAME], excited to connect with you! I’m looking to grow my career in the climate space and thought your experience at [COMPANY] was fascinating. Would love to add you to my network so I can follow along in your journey.
The more relevant people you add to your network, the higher the likelihood that new job postings that are of interest will come into your feed. You’re also increasing your chances of network effects so that the right person for you to meet becomes only a 2nd or 3rd degree connection.
The last point I’ll add is to spend time scrolling through your LinkedIn feed, but time box it. LinkedIn is a social media feed at the end of the day, albeit a more “professional” one, and you can spend infinite hours scrolling. Remember this is only part of the strategy and not the whole strategy when it comes to job search.
💖 What to do when you see a job posting you like
So you’ve done everything above and a connection of yours posted a job that you’re interested in. Now what?
Since you’re connected, you can reach out and send them a direct message letting them know you’d like to put yourself up for the position. Express your interest in a targeted and specific manner. I posted a job a few months ago and this was by far the best inbound message I received:
Similar to the forwardable intro I wrote about above, make it easy for people to understand your interest in the role and how your skillsets map directly to the role at hand. But far too often, I receive messages like this:
This gives the hiring person no context on which role you’re interested in, no sense of how you might be a good fit, and puts the burden on them to figure out why and how they should advocate for you.
Additionally, if you receive a reply and request for more information on how you’re a relevant fit, give them the information but keep it concise. I often ask the candidates in my pool to expound on a few skillsets that I know hiring managers are looking for, and then specifically ask for 3-5 more detailed sentences. Stick to the suggested 3-5 sentences, when asked in your conversations. Most recruiters only spend 6-7 seconds looking at a resume and it’s the same of an introductory email. Not to mention, clear and concise communication is a mandatory skill of any Chief of Staff and your follow up message will reflect that.
🔍 Traditional job search strategies are broken and tired - especially when it comes to Chief of Staff roles. To land a role that is uniquely positioned and relies heavily on creative solutions and nontraditional problem solving, you need to apply those same skillsets even before you’re in the role.
These are the steps I would personally take if I was actively looking for a new Chief of Staff position. If you follow these tactics, let me know how they work out for you! And if you’ve recently landed a Chief of Staff role and you have additional tactics to share, reply to this email and I’d love to include them in an upcoming issue.
Hope you’ve enjoyed the latest issue of this newsletter and we’re looking to you for future newsletter topics! If you have any questions around being a Chief of Staff, tactical takeaways that you can apply, or other curiosities about the Chief of Staff role, submit a question below and we’ll answer it in a future newsletter issue:
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Additional Chief of Staff Related Reads:
How to get a Job as a Chief of Staff
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👋🏼 Until the next issue,
Clara
PS: I’m going to work hard to keep all the content in my newsletter free so that it’s accessible for everyone, but if you want to help support my writing endeavors, you can buy me a matcha or upgrade to a paid subscription 🍵 Special shoutouts to Ashima for supporting the last issue and to the 4 new readers who became paid subscribers!
Shoot me an email at clara@askachiefofstaff.com and I'll send you my network!
Hi Clara! Thank you so much for this post! I would love an invite to your Bridge network.