​What to do. What to avoid. How to build leverage early.

​The first 90 days in a Chief of Staff role can define everything that comes after, but most operators are left to navigate it through trial, error, and instinct.

​In this live Nova Chat, we’ll walk through a clear, phased approach to the first 90 days, focused on learning before acting, making smart recommendations, and building trust and leverage early on.

​Joined by experienced operators and Nova facilitators Maggie Olson, Jillian Hufnagel, and Courtney Vincent, this conversation goes beyond theory and into real-world application: what worked, what didn’t, and what they would do differently if they were starting again today.

​What we’ll cover:

​Phase One: Learn the Business & the Team

• ​Understanding the true Rhythm of Business

• ​Observing decision-making, dynamics, and friction points

• ​Asking calibrated questions that build trust and credibility

​Phase Two: Make Recommendations & Take Action

• ​When to move from observation to influence

• ​Using tools and structure to reduce noise for your leader

• ​Identifying high-impact opportunities and driving clarity

​If you’re EA → CoS

• ​Leveraging what you already know to create strategic value

• ​Translating execution expertise into alignment and priorities

​What not to do in your first 90 days

• ​Common mistakes that slow trust-building and impact

• ​Why moving too fast or over-functioning can backfire

​This session is practical, candid, and grounded in operating experience. You’ll leave with a clear mental model for your first 90 days, and a better sense of where to focus next.

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Can’t attend live? Register to receive the recording.

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​Host and Panelist Bios

​Maggie Olson | Founder at Nova Chief of Staff

​Maggie Olson is the Founder of Nova Chief of Staff, the premier destination for Chief of Staff education, certification, and development. With 20 years of experience in retail, F&B, and tech, she has held leadership roles at Nordstrom and T-Mobile. As the first Chief of Staff to the President of T-Mobile Business Group, Maggie built the Chief of Staff model, establishing a highly efficient team and executive back-office structure supporting the President, SVPs, and over 5,000 employees. Through Nova Chief of Staff, she continues to shape business leadership, equipping Chiefs of Staff with the tools needed for success.

​Jillian Hufnagle | Executive Coach | Strategic Advisor

​Jillian Hufnagle is an executive coach, leadership facilitator, and strategic advisor who partners with founders and senior leaders to navigate growth, complexity, and high-stakes change with clarity and confidence. With over 20 years of experience across startups, SaaS, healthcare, biotech, cybersecurity, and B2B organizations, she specializes in founder coaching, executive offsites, and strategic advisory work that bridges vision, people, and execution. Prior to coaching, Jillian served as the operating “right hand” to multiple CEOs in Executive Assistant and Chief of Staff roles, supporting IPO prep, M&A, executive recruiting, major pivots, and thoughtful wind-downs. She brings a rare blend of emotional intelligence and operational rigor to leadership under pressure.

​Courtney Vincent | Executive Coach | Chief of Staff

​Courtney Vincent, MA, AMFT is a leadership therapist, executive coach, and Chief of Staff with formal training in clinical psychology, marriage & family therapy, and human resource management. She has partnered with 9+ CEOs and executive teams as an Executive Assistant, Chief of Staff, and Head of Operations across mental health, healthcare, biotech, software, and manufacturing. Courtney’s experience spans hyper-growth and wind-down environments—including scaling a startup from ~50 to 3,000+ employees and guiding a company through its final chapter as the last employee. She brings a rare blend of operational rigor and psychological insight, helping leaders build self-aware leadership, high-performing teams, and durable systems built to scale.