How to Know You’re Ready to Hire a Chief of Staff
There’s a moment in nearly every executive’s journey when you realize you’re the bottleneck.
You’ve built something incredible, but the more you grow, the more your calendar fills with meetings, approvals, and decisions that keep you from leading at the level you want. That’s usually when this question pops up:
“Do I need a Chief of Staff?”
But most leaders don’t really understand what a Chief of Staff does or when the time is right to bring one in.
Let’s fix that.
First, What a Chief of Staff Actually Does
At its simplest, a Chief of Staff helps you operate at your highest level of impact. They make sure your ideas become action, your strategy becomes structure, and your team stays aligned while you focus on what matters most.
Depending on your needs, a Chief of Staff might:
Turn your vision into executable priorities.
Lead key initiatives or manage cross-functional projects.
Create systems for communication, planning, and follow-through.
Be your sounding board and thought partner for big decisions.
The specifics vary, but the outcome is the same: less chaos, more clarity, and better results.
7 Signs You’re Ready to Hire a Chief of Staff
1. You’re leading multiple priorities, but finishing few.
Your plate’s overflowing, and you’re spending more time context-switching than creating momentum. A Chief of Staff helps cut through noise and keep the main thing the main thing.
2. You’re the glue holding everything together.
If every decision or update runs through you, that’s not scalable. A Chief of Staff creates structure so your team can run smoothly without you in every detail.
3. Your ideas outpace your team’s capacity.
You see the big picture but your people are buried in execution. A Chief of Staff helps connect strategy to systems, so progress actually matches your vision.
4. Meetings feel busy, not productive.
You’re talking a lot but moving little. Chiefs of Staff specialize in turning meetings into movement and making sure time spent in rooms turns into real results.
5. You’re growing fast and can’t afford to slow down.
Whether you’ve just raised capital or doubled your team, growth without infrastructure leads to burnout. A Chief of Staff scales your operations without the chaos.
6. You need a trusted sounding board.
Leadership can be isolating. And super lonely, if you let it be. A great Chief of Staff brings clarity, honest feedback, and big-picture perspective so you don’t have to figure it all out alone.
7. You want to lead with more calm + less fire-fighting.
You built this business for impact. And your team is more likely to stick around if they’re not constantly fighting fires. A Chief of Staff helps you lead from a place of focus, not constant urgency.
Fractional vs. Full-Time: What’s Right for You
You don’t always need a full-time Chief of Staff. Many leaders start with a fractional partnership where you bring in experienced strategy and operational support part-time or on a project basis.
This gives you access to senior-level thinking and systems without the full-time commitment or overhead (especially useful during seasons of growth or transition!)
The Real ROI
Hiring a Chief of Staff shouldn’t be seen as an expense, but as an investment in your effectiveness as a leader. It’s the difference between doing more work and creating more progress.
When you have someone connecting the dots between vision and execution, you free up your time, focus, and energy to lead at the level your business now requires.
If you’re asking whether it’s time to hire a Chief of Staff, you’re probably closer than you think.
The question isn’t “Can I afford one?” It’s “How much longer can I afford to lead without one?”
Final Thought
Hiring a Chief of Staff isn’t about admitting defeat. You’re clearly an ambitious, talented human being. Bringing on an executive partner is about designing for the long-haul.
When you stop doing it all yourself, you gain capacity to focus in on your zone of genius. You free yourself to lead the way you were always meant to: clearly, calmly, and with space to think again.
Considering hiring a Chief of Staff?
Whenever You’re Ready, Here Are 3 Ways We Can Work Together:
Follow Me on LinkedIn. For insights on leadership, clarity, and getting the most out of the Chief of Staff role. Follow along for quick hits and real talk about making work work.
Hire Me as Your Chief of Staff. Not sure if you need a Chief of Staff? Let’s talk it through. Book a quick discovery call to find the right fit for where you’re headed.
Collaborate With Me. Work with ambitious leaders, too? Let’s dream up a win-win: podcasts, panels, trainings, or creative partnerships that help more people lead well and live well.
