Leland+ for Chief of Staff
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Myths and Tips About Chief of Staff Roles
What’s a Chief of Staff and why are these roles so popular now? The CoS role isn’t just for government anymore. These days, the important roles are everywhere. Join us to learn the real info about these roles from former 8x Chief of Staff Cherizza L. Cherizza’s been a CoS at Google, Stitch Fix, Intel, on campaigns and in non profits. She’s been in the room and she’s sharing the goods!
Mastering the Chief of Staff Interview
Join us for a practical breakdown of what top Chiefs of Staff look for when hiring this uniquely high-leverage role. Expert Leland Coach and ex-Google and Stitch Fix CoS Cherizza L. will cover how to tell your story, demonstrate strategic thinking, and show you can operate as a true force-multiplier to executives. You’ll gain insight into the interview styles, case prompts, and signals that matter—so you can walk in prepared, confident, and ready to stand out.
Chief of Staff 101 FAQ
An unfiltered guide to CoS. Learn what the job actually entails, who thrives in it, how to break in, and what no one tells you until you're in.
Translating Military Leadership into a Chief of Staff Role
Military leaders bring exactly the kind of operational rigor, decision-making under pressure, and cross-functional leadership that Chief of Staff roles demand, but translating that experience for civilian employers can be tricky. In this session, you’ll learn how to reframe military responsibilities into executive-ready language, position your leadership experience for strategic Chief of Staff roles, and avoid common pitfalls that can undersell your impact. Whether you’re transitioning now or planning ahead, you’ll walk away with a clearer playbook for turning military leadership into a compelling Chief of Staff candidacy.
Nailing the Chief of Staff interview
Landing a Chief of Staff role starts with acing the interview—and that can be one of the biggest hurdles for top candidates. In this session, you’ll hear from Julianne Z., a two-time Chief of Staff with experience across private equity and VC-backed companies. Julianne will walk you through what CoS interviewers are evaluating at each stage, how to frame your thought process under pressure, and how to draw on your past experiences to position yourself as an indispensable partner to leadership. You’ll also learn how to handle tough questions, structure your responses, and avoid missteps that derail many CoS candidates. Whether you’re interviewing for your first Chief of Staff position or trying to level up your candidacy, this session will give you clearer insight and tangible prep strategies.
What Does a Chief of Staff Really Do? AMA with an Ex-Google Ops Leader
Curious about what a Chief of Staff actually does day-to-day and how to prepare for one of these high-impact roles? Join Regan R., former Strategy & Operations leader at Google Cloud and current Chief of Staff at Verily (and a Harvard MBA), for an AMA where she’ll pull back the curtain on the role—from leadership mindset and stakeholder alignment to career trajectory and essential skills. Bring your questions and walk away with a clearer sense of what it takes to thrive in this unique role and how to prepare accordingly.
Tips & Tricks for Applying & Interviewing for the CoS Role
Landing a Chief of Staff role takes more than luck—it requires a clear strategy for how you present yourself, connect with the right people, and stand out in interviews. In this session, experienced Chief of Staff and hiring expert Sivan R. will break down the process into three actionable parts: Tailoring the Resume – How to position your transferable skills, highlight impact, and use the key words hiring managers are looking for. Elevating the Outreach – How to identify the right people to get you in the door, craft effective messages, and build meaningful connections. Mastering the Interview – How to prepare with confidence, anticipate common Chief of Staff interview themes, and tell your story with clarity. By the end, you’ll have a clear playbook for navigating the Chief of Staff application process from start to finish—equipped with practical tips you can put into action right away.
