When to bring in a Chief of Staff: Real signs it’s time (and how to get it right)
- LBM
- Apr 11
- 3 min read
Updated: Apr 11
You’re leading the company.
But you’re also chasing status updates.
Still rewriting strategy into slides.
Still stepping into meetings just to clarify priorities.
You’re not inefficient. You’re over-embedded.
And the business is scaling faster than your time or context can stretch.
That’s when most CEOs start to consider hiring a Chief of Staff.
But the question isn’t if. It’s when, and why.
What a Chief of Staff actually does
A Chief of Staff is not a junior COO.
They’re not a fancy title for a project manager.
And they’re definitely not just a high-context EA.
The right CoS is a systems integrator around the principal.
Someone who protects your time, sharpens your focus, and turns strategic ambiguity into coordinated execution.
Translate your intent into company-wide clarity
Build decision loops and leadership rhythm
Preempt misalignment across fast-scaling teams
Clear your cognitive load by managing internal priorities, not tasks
Amplify your leadership signal without you needing to repeat yourself
They don’t run departments.
They don’t own functions.
They connect them, quietly, effectively, and without pulling attention back to you.
In many cases, this becomes the foundation for an Office of the Principal, not a job title, but a structure around the CEO or founder the company still depends on.
When the timing is right
Here are 3 important triggers when to bring in a Chief of Staff.
1. When you’ve hit product-market fit, but execution is still people-dependent
You’ve got traction.
You’re hiring.
But you’re still in every critical loop.
If execution slows when you’re offline, or if priorities lose shape after you announce them, your company doesn’t just need more people.
It needs a system for clarity and follow-through.
This is when a CoS can help you stabilize internal operations before chaos calcifies.
🔗 Related: Three-Layer Execution Model
2. When you’re forming your first leadership team
You’re starting to delegate ownership.
But ownership without structure becomes siloed quickly.
Everyone’s rowing, but not in sync.
A Chief of Staff coordinates leadership, builds your internal cadence, and ensures decisions don’t evaporate between meetings.
This prevents your org from becoming “busy” without being aligned.
3. When you’re scaling faster than you can communicate
You’re fundraising.
Expanding.
Shifting focus.
And still managing weekly planning.
This is the moment when your time becomes the bottleneck.
A CoS isn’t there to “take things off your plate.”
They make your plate smaller:
Narrow your loops from 12 to 3
Enforce internal discipline so you don’t have to
Keep the team close to your thinking, without pulling you into tactical comms
If you wait too long, you end up hiring a CoS into dysfunction.
Or worse: into an EA-shaped role that frustrates everyone involved.
What makes the CoS timing unique
Unlike other roles, the CoS adapts to your org’s shape:
Company Stage | What CoS Focuses On |
Early / post-PMF | Filling gaps, keeping leadership clear, managing context overflow |
Scaling startup | Planning cadence, decision hygiene, internal clarity |
Later stage / corp | Cross-functional coordination, staff comms, strategic initiative mapping |
It’s not about headcount.
It’s about whether you, the principal, can scale without replicating yourself.
Still unsure if it’s time? When to bring in a chief of staff?
Here are strong signals:
You repeat yourself across functions
Execution slows when you’re not driving it
You get updates, but not clarity
You’re making decisions faster than the team can follow
You’re needed in every room to keep things moving
This doesn’t mean you’re failing.
It means your organization has outgrown your current system, and needs also someone who thinks across it, to make you focused on other high value activities.
That’s what a Chief of Staff does.
If you’re not ready to hire one full-time, start with a Chief of Staff Sprint, a focused engagement that installs structure around leadership and clears internal noise.
Map your current system architecture
If you’re on the edge of this decision, let’s map your current architecture, bandwidth, and leadership model.
You’ll leave the call knowing if a CoS is the next hire, or if something else needs to be designed first.
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