You Don’t Need a Chief of Staff. Until You Really, Really Do.
Most founders I know are moving fast. The calendar is full, the ambition is real, the effort is obvious to everyone in the room.
And yet something, as they tend to put it, isn’t quite landing. Decisions get made and don’t travel. The same problem that appeared in Q1 reappears in Q3 wearing a slightly different hat. Strategic conversations happen and are absorbed by the week. The company is in motion, but not obviously moving forward. This is usually described as a capacity problem. It’s almost never a capacity problem. It’s an orchestration problem, which is different and won’t be solved by hiring faster.
The instinct when things feel stuck is to add structure. A COO. A senior hire. A new project management platform. Or the perennial favourite: “we need better alignment,” announced at the end of an offsite and achieved, in my experience, approximately never. These aren’t wrong instincts exactly, but they tend to reach for the wrong instrument. What’s missing isn’t hierarchy or tooling. It’s a person occupying the gap between what the founder intends and what the organisation actually does next.
The signs are fairly consistent. Decisions require the founder’s personal follow-up to stick. The company’s strategy exists primarily in one person’s head. Everyone is occupied; progress is thin. The founder is spending working hours tracking updates rather than making decisions worth tracking. None of this signals failure. It signals that the company has quietly outgrown the operational model that got it here. Growth doesn’t break organisations. Unmanaged complexity does.
A Chief of Staff is not an executive assistant with a grander title, and not a junior COO to whom you hand the chaos and hope for the best. The role, when it works, is about designing clarity and then maintaining it. The CoS sits close enough to leadership to see the whole system, moves decisions forward without requiring the loudest voice in the room, and asks, in the meeting, the question everyone else has quietly agreed to leave unasked.
The net effect is that the founder’s thinking becomes the company’s behaviour, which sounds simple and turns out to be quite rare.
There is also a case for not hiring one yet. If the team is under ten and still forming, if decisions are simple and reversible, if the founder is still usefully embedded in day-to-day work, a Chief of Staff is probably leverage applied before there’s anything to lever. Getting the timing wrong in either direction is expensive.
When the fit and timing are both right, the change is genuinely hard to describe because it mostly manifests as an absence of friction. Decisions are carried forward without chase. Leaders think ahead rather than react. The founder recovers cognitive space, not just calendar space. The company stops running on momentum and starts running on something more like rhythm.
The best Chiefs of Staff are nearly invisible. Until you try to imagine operating without one.
Is It Time for a Chief of Staff… or Are You Still White-Knuckling It?
