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, is not quite landing.
Decisions get made and do not travel. The same problem that showed up in Q1 reappears in Q3 wearing a slightly different hat. Strategic conversations happen and get absorbed by the week. The company is in motion but not obviously moving forward. This usually gets described as a capacity problem. It is almost never a capacity problem. It is an orchestration problem, which is a different thing, and hiring faster will not solve it.
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 are not wrong instincts exactly, they just reach for the wrong instrument. What is missing is not hierarchy or tooling. It is a person occupying the gap between what the founder intends and what the organisation actually does next.
The signs are consistent. Decisions need the founder’s personal follow-up to stick. The strategy lives mainly in one person’s head. Everyone is busy and progress is thin. The founder spends working hours tracking updates rather than making decisions worth tracking. None of this is failure. It means the company has outgrown the operating model that got it here. Growth does not break organisations. Unmanaged complexity does.
A Chief of Staff is not an executive assistant with a grander title, and not a junior COO you hand the chaos to and hope. The role, when it works, is about designing clarity and then maintaining it. The Chief of Staff sits close enough to leadership to see the whole system, moves decisions forward without needing the loudest voice in the room, and asks, in the meeting, the question everyone else has tacitly 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 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 the day-to-day, a Chief of Staff is leverage applied before there is anything to lever. Getting the timing wrong in either direction is expensive.
When the fit and the timing are both right, the change is genuinely hard to describe, because it mostly shows up as an absence of friction. Decisions get carried forward without chasing. Leaders think ahead instead of reacting. The founder gets back cognitive space, not just calendar space. The company stops running on momentum and starts running on something closer to rhythm.
The best Chiefs of Staff are nearly invisible. Until you try to imagine operating without one.
Related: Recruiting a Chief of Staff: read this before you post the job spec.
