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Package Description:
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.
What you'll get from this package
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
Additional details
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
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Offered by Gaylan G.
Joined October 2021
✨ You're Chief of Staff coach with 11 years of Naval Leadership experience
With extensive experience in strategic leadership and operational excellence, I am exceptionally qualified to serve as a Chief of Staff Coach on Leland, guiding professionals seeking to excel in this pivotal role. My background includes over 11 years as a Naval Officer, culminating in my position as Deputy Chief of Staff to the Navy Chief of Legislative Affairs, who reports directly to the Secretary of the Navy and the Chief of Naval Operations. In this capacity, I collaborated closely with US Senators/Congressmen and Senate/House Committee staff, managing high-stakes legislative initiatives and ensuring alignment across executive branches. Complementing this, my five years in product management at leading tech companies such as Amazon, LinkedIn, and Guideline have refined my expertise in cross-functional coordination, strategic planning, and driving organizational priorities to achieve measurable results. As a coach, I am dedicated to empowering people to break into the Chief of Staff role and enhance their strategic leadership capabilities. My approach draws from proven experience as a strategic partner in executive stakeholder management, optimizing operational workflows, and delivering high-impact organizational outcomes in dynamic environments. By providing tailored guidance on frameworks such as OKRs, stakeholder mapping, and strategic communication, I equip people with the tools to articulate their value, build executive trust, and navigate complex challenges effectively. My commitment is to offer people actionable strategies and personalized mentorship to realize their Chief of Staff aspirations with confidence and precision.
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5h+ of coaching