Cover Image for [Webinar] Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now
Cover Image for [Webinar] Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now
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The Offsite Calendar is your hub for curated gatherings designed for Chiefs of Staff, People leaders, and executives to build meaningful connections.

[Webinar] Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now

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About Event

Over the past 12–18 months, we’ve seen something interesting…

Every high-growth company seems to be hiring a Chief of Staff.

But ask five companies what that role actually does, and you’ll get five completely different answers.

  • Some Chiefs of Staff are running exec offsites and driving alignment.

  • Others are acting as extensions of the CEO.

  • Some are basically operators… and others still are strategic advisors.

ALL are figuring it out in real time.

So what does a “great” Chief of Staff actually look like in 2026?

And what will this role look like in the next 12-18 months with AI and other advances in technology?

We’re bringing together Clara Ma (founder of Ask a Chief of Staff) and other experienced operators to break down what’s really happening inside the role right now… what’s working, what’s not, and where it’s all heading.

In this live session, we’ll cover:

  • How the Chief of Staff role has evolved over the past year (and why expectations are changing fast)

  • What high-performing Chiefs of Staff are actually spending their time on

  • The biggest challenges Chiefs of Staff are facing in 2026 (and how they’re navigating them)

  • How the role differs across company stages, founders, and leadership teams

  • Where Chiefs of Staff are driving the most impact right now (hint: it’s not just meetings and notes)

This isn’t a generic panel.

It’s a candid conversation with people actually in the role… sharing what they’re seeing behind the scenes.

If you’re a Chief of Staff, work closely with one, want to be promoted into the role, or are thinking about hiring a Chief of Staff… this is worth your time.

Save your spot today!

Avatar for The Offsite Calendar
The Offsite Calendar is your hub for curated gatherings designed for Chiefs of Staff, People leaders, and executives to build meaningful connections.