Ask a Chief of Staff: What Your CEO Is Afraid to Tell You
🗓️ Join us on July 31st!
Being a CEO is lonely. They’re always afraid of something— whether it’s missing the market, losing the team, or running out of time. But they rarely say it out loud, even to the people they trust most. In this RealTalk session, Mark Josephson — executive coach and 3x former CEO — will share the hard truths your CEO is carrying, why they’re not telling you, and what the best Chiefs of Staff do to earn that trust. You’ll walk away with a deeper understanding of your CEO, the emotional weight of the role, and simple, powerful ways to become the person they turn to when it matters most.
In this interactive workshop, Mark will cover key insights from his coaching work with venture-backed CEOs, share real-world examples, and offer practical scripts and habits you can use right away. Cameras on, questions encouraged. You'll hear the hard stuff, build real trust, and become indispensable.
✅ You should attend this workshop if...
You want a better understanding of what your CEO is carrying—but not saying;
You want to build deep, durable trust with your CEO
You want to avoid the common mistakes Chiefs of Staff make in high-stakes moments;
You want to level up from executor to trusted partner;
You want actionable tactics, not just leadership theory.
🎟️ Please note, there will be a 100-person limit on this event. If you are unable to attend live, we will send a recording of the event afterwards.
🎙️ More about the Speaker
Mark Josephson is an executive coach and 3x CEO who has built and led companies from seed stage through acquisition, including Bitly, Outside.in, and Castiron. Today, he works with high-growth CEOs and Chiefs of Staff to help them lead with clarity, candor, and confidence. Known for his no-fluff, RealTalk style, Mark brings decades of operating experience to his coaching practice. He writes the How to CEO series on Substack and hosts the Critical Moments podcast.
💜 Ask a Chief of Staff
Ask a Chief of Staff is a premier executive search and career development platform dedicated to placing top-tier Chiefs of Staff and empowering professionals in strategic leadership roles. We serve ambitious professionals and high-growth companies by offering executive recruiting, mentorship programs, and career resources tailored to Chiefs of Staff. By addressing the lack of structured career paths for this role, we provide guidance, connections, and opportunities that accelerate leadership development and organizational success.
Learn more at askachiefofstaff.com.
👋🏻 Disclaimer
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