We had a client recently, who is in rapid growth mode. They needed to hire several positions, including an HR director, chief revenue officer, administrative assistant, and a COO/Integrator. The Visionary was overwhelmed and wasn’t sure where to begin. This is a common frustration leaders have when they are in growth mode and need to make multiple key hires. The question is where to begin?
There are lots of different approaches leaders can make when they need to make multiple hires like this. Some choose to hire the least expensive roles first, some leaders choose to higher the most impactful roles first, some leaders choose to hire the easiest roles first, and some feel so overwhelmed they don’t do anything.
When looking at these types of roles for a leader our recommendation first and foremost is to hire an administrative assistant. This role can be a game changer for the Visionary as it frees them up from a lot of administrative activity and gives them much more time. It’s also generally an easier role to hire for, but has lots of different complications (virtual EA are also a strong option for the leader). Before the Visionary hires their executive assistant, they need to map out exactly what they’re looking for out of the role and then make this higher first.
The next priority for a Visionary is to get their number two on board. Whether this is called an Integrator, COO, or Chief of Staff, doesn’t matter; this is the person who is going to be responsible for all the other openings. We do not recommend hiring positions that will report to a COO who is not yet in place because the COO is now going to inherit these newcomers. We recommend getting the COO in place first and letting them be responsible for hiring the rest of the team. The COO is going to own these hires and it is important for them to be involved in making the hiring decision and for the new hires to be comfortable with who their boss is going to be.
So the short answer when a Visionary is growing rapidly and looking at multiple hires is first bring on that executive assistant, and second bring on the COO/Integrator. After that, let the COO decide who to bring on next and how.
Making Multiple Key Hires: Where Growth-Stage Leaders Actually Get Stuck
Growth doesn’t announce itself politely.
One quarter everything feels manageable. The next, four roles are suddenly open at the same time. HR leadership, revenue leadership, administrative support, and a true #2. Each one feels essential. Each delay feels risky and every decision seems like it could either unlock momentum or create months of drag.
This is the moment many founders recognize they can’t keep carrying the organization the way they have been. It’s also the moment where hiring decisions quietly become harder, not easier.
When Everything Feels Urgent, Leaders Freeze
The tension isn’t indecision. It’s overload.
As growth accelerates, decisions start rolling uphill. The founder becomes the default owner of context, coordination, and judgment. Every open role depends on the same person to define success, make tradeoffs, and hold the whole picture together.
When multiple key hires are on the table at once, leaders often feel pressure to “just start somewhere.” What looks like hesitation from the outside is usually a signal the process for sequencing hires hasn’t kept up with the scale of the business.
The Common Misdiagnosis: It’s Just a Prioritization Problem
In this situation, leaders tend to default to familiar logic.
Some hire the least expensive role first to protect cash.
Some chase the most impactful role, hoping it will fix everything else.
Some pick the easiest role to fill, just to regain momentum.
And some delay all of it, absorbing the pressure themselves.
Each choice sounds reasonable. Each one misses the real constraint.
The issue isn’t prioritization. It’s that leadership capacity and ownership are being addressed too late.
The Real Process Gap: Capacity Comes Before Capability
When multiple hires are needed at once, the first thing that breaks is not talent. It’s capacity.
Administrative work, scheduling, follow-up, and coordination quietly consume the founder’s attention. Strategic thinking gets fragmented. Hiring decisions become reactive. Even strong leaders start making judgment calls under pressure.
Until that capacity constraint is relieved, every additional hire increases risk.
This is why the first role that stabilizes growth is rarely the one leaders expect.
Why the First Hire Creates Leverage, Not Just Help
The role that most quickly changes the equation is administrative support.
Not because it is strategic on paper—but because it gives the founder their time back.
When this role is clearly defined, it absorbs operational noise that doesn’t require founder-level judgment. Space opens up for clearer thinking, better role definition, and more deliberate hiring decisions downstream.
When it is poorly defined, it becomes another source of friction. Expectations blur. Delegation fails quietly. The role ends up reactive instead of stabilizing.
The difference is not effort or talent. It is whether success for the role was explicitly designed before hiring.
Why Ownership Must Be Established Before the Team Is Built
Once capacity is stabilized, the next failure point becomes visible: ownership.
Whether the role is called COO, Integrator, or Chief of Staff, this is the person meant to own execution and accountability across the organization. This role does not exist to add leadership—it exists to absorb responsibility that currently sits with the founder.
When leaders hire downstream roles before this person is in place, they create inherited misalignment.
New hires arrive without a long-term owner. Reporting lines change. Expectations shift. The future #2 is asked to lead decisions they were never part of shaping.
What follows is rework, restructuring, and frustration—often misattributed to the people involved rather than the order in which roles were designed.
What Quietly Breaks When the Order Is Wrong
Sequence errors don’t announce themselves.
They show up later as stalled leadership development, inconsistent accountability, and performance conversations that never seem to land. Teams feel the instability even when leaders can’t name it. High performers get frustrated by shifting expectations. Trust erodes slowly.
At that point, organizations often invest in coaching, training, or development programs to fix what feels like a people problem.
But the root cause sits earlier in how roles were sequenced and ownership was established.
The Order That Reduces Risk
When growth demands multiple key hires, the stabilizing move is not speed. It’s order.
First, restore capacity so the founder can think clearly again.
Second, establish ownership so execution has a natural home.
Only then does it make sense to build out the rest of the leadership team.
Once a true #2 is in place, decisions about HR, revenue, and operations stop competing with each other. Roles are designed with their future leader involved. Accountability has somewhere to live.
If this feels familiar, the frustration isn’t personal. It’s structural.
This moment doesn’t require better instincts. It requires a hiring process that matches the scale of the business.
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