How to Know When it’s Time to Hire a Chief of Staff in a “Small” Company

If you’re leading a small to mid-sized business or family office, chances are you’ve built something meaningful. You’re the person people come to for decisions, direction, and reassurance. You hold the vision, the relationships, the nuance. And lately, you’re holding a lot! 

You may not call it overwhelm; but you feel it.

The calendar is packed. The inbox is layered. The strategic work (the stuff that actually moves the needle) is getting squeezed between approvals, logistics, and “quick questions.”

This is often when someone says, “You need a Chief of Staff.”

And you pause.

Because you’re not sure what that means.

And also, aren’t Chiefs of Staff for tech CEOs and political leaders?

Let’s clear that up.

A Chief of Staff is a strategic partner who helps you run the business you’re already building.

They’re not a second CEO.

They’re not an assistant.

They’re not a fixer, a ghostwriter, or a shadow.

They’re the person who holds context, connects dots, and helps you lead more efficiently.

They make your leadership feel like you again.

What a Chief of Staff Actually Does

In a small or mid-sized business, a Chief of Staff might:

• Run point on internal operations and cross-functional projects
• Prepare you for board meetings, investor updates, or team offsites
• Shape messaging and tone across the company
• Spot risks before they become problems
• Hold the rhythm of the business so you can hold the vision

They’re often the person who knows what’s happening before it happens.

They’re trusted, discreet, and deeply attuned to how you lead.

Signs You’re Ready

1. You’re the bottleneck.
   Decisions wait for you. Approvals wait for you. People wait for you. And you’re starting to feel like the company’s growth is tied to how fast you can type.
2. You’re context-switching so often it feels like a sport.
   One minute you’re reviewing a contract. The next you’re brainstorming a product name. Then you’re in a hiring debrief, followed by a budget review, followed by a Teams message that says “Got a sec?”
3. You’re craving more time for the work only you can do.
   Vision. Relationships. Culture. The stuff that doesn’t fit in a task manager but defines everything.
4. You’re hiring fast and building even faster.
   And you need someone who can help shape systems, hold context, and make sure your team isn’t just moving quickly but moving well.
5. You’re tired of being the only one who sees the whole picture.
   A Chief of Staff doesn’t just manage tasks. They manage meaning. They connect dots, hold tension, and help you lead with precision.

What It’s Not

Hiring a Chief of Staff is not a sign that you’re overwhelmed.

It’s a sign that you’re ready to lead differently.

It’s a sign that your business has reached a level of complexity that deserves strategic support.

It’s a sign that you’re building something worth protecting, and worth growing with care.

And when you find the right one

You’ll wonder how you ever did it without them.