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Here’s the Chief of Staff paradox: you’re exceptional at what you do, but there’s no clear ladder to climb. You’ve learned to flex across functions, speak every department’s language, and make your principal wildly successful—but what does all that experience actually add up to for your career?
This workshop cuts through the noise with a deceptively simple framework: Operating Principles, Strengths, and Passion Areas. No more analysis paralysis or FOMO about closing doors. Just a clear lens for evaluating what’s next based on who you actually are—not just what looks good on paper.
If you’re 3️⃣ years in and wondering “is this it?” or navigating leadership turnover and questioning your path, this is your roadmap out of the trap.
Cydnee DeToy is a career coach and speaker who’s helped over 1️⃣ 1️⃣ 0️⃣ ambitious women design careers that actually align with their lives. As a former Chief of Staff who managed a team of 7️⃣ while supporting 3️⃣ co-CEOs simultaneously, she intimately understands the unique challenges of the role—the access, the ambiguity, and the “now what?” moment that inevitably comes.
Cydnee brings experience from strategy consulting, C-suite leadership, and Head of People roles, plus an MBA from NYU Stern and certification from the Co-Active Training Institute. She’s worked with clients at Meta, BCG, Bain, and numerous startups.
This isn’t your typical career planning session. Cydnee introduces a 3️⃣ part framework designed specifically for multi-talented generalists who struggle with having too many options (and not enough clarity). Through guided reflection questions and real examples, you’ll learn how to identify what truly matters to you—both professionally and personally—and use that as decision criteria for your next role.
The workshop includes practical tools you can use immediately, plus extended Q&A where Cydnee coaches attendees through real career dilemmas like navigating internal moves, escaping pigeonholing, and managing the FOMO that comes with closing doors.
Why being exceptional at everything makes it harder to know what’s next
The unique challenge of a role with no clear ladder or conventional next step
How supporting others’ success can obscure your own career development
The mix of values, priorities, and anchors (professional AND personal) that make you feel grounded and aligned
Why “whole human” matters as much as “quality time with stakeholders”
How to identify the conditions under which you actually thrive (not just survive)
The critical difference between learned strengths and innate abilities
Why your function (not your industry) dictates 80% of your daily satisfaction
How to translate Chief of Staff skills for other roles without losing your value
Identifying the topics, industries, and challenges you want to meaningfully impact
Moving from “I could do anything” to “this is what I actually want”
Building your legacy criteria (what do you want to have changed?)
How to generate your “long list” of possible next moves
Narrowing to a short list using your three framework pieces as decision criteria
Finding the right answer between your spreadsheet and your gut
Managing FOMO when you have multi-hyphenate talents
Escaping pigeonholing when you’re “too good” at things that don’t energize you
Telling your story when making an internal move (especially during leadership chaos)
Building your value proposition as a generalist in a specialist world
Whether you’re a current or aspiring Chief of Staff, I invite you to check out the Ask a Chief of Staff community. We’re now 4️⃣ 5️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:
💬 Members-only Slack workspace for peer support & real time question answering
🖥 Exclusive workshops & events (virtual & in-person)
🤝 A supportive network of peers facing similar challenges
🧑💼 Direct access to experienced Chiefs of Staff and mentors
🌟 Curated job opportunities from leading companies
🙌 Resources and frameworks for immediate impact
Visit our website and click the “Join our community” button to start your journey!
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