How to Leverage your Chief of Staff Experience to Find a Dream Job

My experience as a Chief of Staff (twice!) prepared me to excel at almost any job that requires someone to focus on building team alignment, maintaining a macro perspective, and comfortably working cross-functionally. Here’s how I approached my job search, and found my dream job, without knowing exactly what I wanted.

Emotionally Begin Your Search

  • Be honest about the parts of your last role that you hated. Don’t pursue a role that focuses on these parts. Just because you can doesn’t mean you should.

  • Check your ego. Your proximity to power as a Chief of Staff wasn’t actually power. Unless you’re joining a tiny startup, your next title probably won’t start with a C and you probably won’t report to the CEO.

  • Keep an open mind about where your Chief of Staff experience can take you and explore as many opportunities as possible. Your goal should be to have as many conversations as possible so you can learn about your options.

  • Create your dream wishlist. Go hog wild. Don’t worry, no one has to see it. Let your mind expand as far as possible. In my experience, this exercise made me aware of opportunities that tangentially hit most of my list. To appreciate the nuance of an opportunity, we first have to be aware that it is an opportunity. 

Tactically Begin Your Search

  • Save searches for the parts of the role that you enjoyed the most e.g. external communications, alignment building, culture, strategy so you can learn the titles and types of jobs that most often appear for these keywords. 

    • During my late 2019 search, I used Google job search because it aggregates postings from most websites & LinkedIn

    • Receive results daily & commit to reviewing these emails daily. You’ll start to see trends and can use this data to refine your search.

    • Note the vocabulary and use it to expand your search: alignment = OKRs = Workboard, Betterworks, 15Five

    • Do the same for any title that sounds interesting to learn the associated vocabulary & to practice mapping your experience to another role’s requirements.

  • If you want to jump industries, educate yourself about the key challenges, and frame your experience in the context of what these organizations likely need. What phase of growth are they in / what are the growth phases in their industry? What macro-economic forces are impacting their industry now?

  • Create a list of 100 leaders you’d love to work for. Pat yourself on the back when you get to 50. This task will require you to research companies/leaders and begin to create filters based on what’s most personally interesting.

  • Find lists of questions, write answers, and then practice out loud. Get comfortable talking about yourself and using 1-2 experiences to answer 80% of the questions. Talking out loud, without looking at your written answers, will help you identify which questions trip you up and require practice. 

Meet, Talk, Rinse, Repeat

  • When explaining the previous Chief of Staff role in your cover letter or resume, focus on the parts that apply to what you want to do next e.g. working cross-functionally, working on strategy & tactics. If the role doesn’t require interfacing with the Board of Directors, position that experience more generically e.g. Experience communicating to and collaborating with C-Suite and Board-level leadership

  • Cold contact your target list of 100 (above). Seriously.

    • Buy LinkedIn premium (it’s the best $60-ish dollars you can spend) to research targets

    • Use a tool like Hunter.io to find email address

    • Craft an email that focuses on the value you want to bring that person’s company & send it off

    • Include a link to your website

    • If the email bounces back, use your LinkedIn credits

  • Success = Opportunity + Preparation. This method WILL get you conversations. Your job is to be over-prepared. Prior to any conversation, digest everything you can about the person and the organization. YouTube videos, Tweets, blog posts, personal websites, LinkedIn pages, Glassdoor reviews, AngelList pages. Anything you can find. Use this prep to ask smart, C-level questions about the company’s priorities and current challenges.

  • Say yes to every conversation. The hiring manager in me hates this because I would only want to talk to someone seriously interested, but it’s important to take every opportunity to practice your narrative. Keep an open mind as project work may pop up, or the hiring manager may change companies and pursue you to join her team elsewhere.

In the Interview

  • Learn from every conversation. What about your pitch resonated, where did it fall flat, where you did stumble over your words, what do you want to do differently next time?

  • Use your Chief of Staff wizardry to help your interviewers map your skills to the role. As Chiefs, we’re often expert listeners with high emotional intelligence. Use these skills in your interview process to tease out what matters most to the hiring manager and feed the flow of the conversation

  • Share your experience managing problems that never appear in job descriptions. Did you help bind a fragmented exec team? Help breakthrough to a non-communicative leader? I can’t imagine a job description that reads “responsibilities include trying to mend the broken relationship between this position’s boss and the rest of the company”, but that might be exactly what the company needs. 

  • Do 80% of the work for the hiring manager, just as you did for your principal. Shortly before the last round of the interview process, prepare a 90-day plan for how you would tackle the role. Show your work, make your assumptions obvious (just as you did to earn partial credit back in school!). Make it easy for your future boss to say “you have most of it, but here’s what I’d change”. It’ll show your initiative, that you’re willing to do the work to make their job easy, and it’ll give a blueprint for success before you start in the role.

Job search resources

  • Tim Guthrie’s OneJob substack a weekly free newsletter (or triweekly $12/month newsletter) with “under-the-radar opportunities at top startups”. A lot of Chief of Staff & Chief-of-Staff-like roles in SF & NYC.

  • Invest in a professional resume writer. This paid for itself almost immediately via inbound interest that helped me learn more about what I want.

Alicia DiamondChief of Staff