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This package is designed for candidates preparing to excel in Chief of Staff interviews, where strategic thinking, executive communication, and adaptability are key. With customized preparation and 1-on-1 coaching, you’ll build the confidence and skills needed to perform strongly in both scenario-based strategic interviews and behavioral interviews, positioning yourself as an indispensable partner to senior leadership. Key components of this package include: - Deepening your understanding of Chief of Staff interview themes such as executive problem-solving, prioritization, cross-functional alignment, and organizational effectiveness - Framework development sessions to help you structure solutions to strategic and operational challenges clearly and persuasively - Mock interviews (strategic cases and scenario questions) with detailed feedback to refine your approach and sharpen your responses - Behavioral interview preparation to craft compelling stories that highlight leadership, adaptability, and impact across diverse situations - Company- and executive-specific research to tailor your answers and demonstrate insight into leadership priorities - Techniques for effective communication, executive presence, and structured storytelling - Strategies to manage ambiguity, stress, and high-pressure questions with composure - Continuous improvement through iterative feedback, tailored drills, and practice sessions By the end of this package, you’ll have honed the unique interview skills required for Chief of Staff roles, developed a compelling personal narrative, and gained the confidence to stand out in interviews and secure the offer.
Refined interview techniques through mock interviews with detailed feedback
Compelling behavioral stories that effectively highlight your skills and experiences
In-depth knowledge of industry and company-specific information to tailor your responses
Strategies for managing stress and maintaining composure during interviews
Coaching delivered via live sessions and .
Additional expectations or terms of engagement may be provided by coaches (e.g. expected response times, etc.).
Services included:
Interview Prep
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
$80110h of coaching
Expert help on everything from getting the interview to landing the offer.
$2,06420h of coaching
Targeted coaching to help you break into Chief of Staff roles
Starting at $6125h+ of coaching
Get help with Interview Prep, LinkedIn Review, and .
Katy also coaches for MBA, Career Coaching, and Leadership Coaching. View all.
Joined January 2025
5.0
Former Chief of Staff (now COO) of YCombinator-Backed Startup
I'm an experienced startup Chief of Staff; I served as a fractional Chief of Staff for 10+ companies as a self-employed startup consultant, and later joined one of my clients (a YCombinator-backed leading Democratic political tech startup) in-house as founding Chief of Staff. I was later promoted to COO of the same company, which I've led for several years. Importantly, I've been an informal leadership coach and Chief of Staff mentor to numerous peers and junior staffers along my journey. I have formal experience developing a coaching and professional development program for second-in-command executives. I'm extremely familiar with the unique dynamics and demands of the Chief of Staff role - as a middleman between executives and staff, as a combined strategist-and-executor, and all of the other many ways that being a Chief of Staff is different than almost any other role in the professional world. I'm here to help you find a Chief of Staff role for the first time, and/or navigate a new role as a Chief of Staff.
5h+ of coaching