Most mid-market CFO departures we see are set in motion between month 15 and month 20 of tenure. The chair conversation that would have prevented most of them is short, direct, and rarely happens.
Here is the conversation.
When to have it
Around month 18. Not month 12, which is too early because the CFO is still landing. Not month 24, which is too late because the decision has usually been made by then.
The window is roughly month 17 to month 20. Book 45 minutes. In person if possible, private, no CEO in the room.
What to open with
Not the annual review. Not a performance framing. A specific opening question:
"You are 18 months in. I want to have an honest conversation about how you are finding the role, whether it is what you thought it would be, and what you would want to change. Not the version you would say to the CEO. The version you would say to me."
Then be quiet. The pause after that question is the most important part. Most CFOs will pause because nobody has framed the conversation this way before.
What to listen for
Three specific things.
Gap between the job as pitched and the job as experienced. Every CFO finds the role slightly different from what they expected. The question is how much, and how much it bothers them. A CFO who describes small gaps has a manageable friction. A CFO who describes large gaps is often at the early stages of deciding to leave.
Which parts of the mandate they wish they could hand off. Strong CFOs, given permission, will name the parts they find most draining. Sometimes those parts can be structurally shifted (a stronger number two, a different reporting cadence). Sometimes they cannot. Naming them is what matters.
Whether they have been approached recently. Not in a paranoid way. Direct. "Have you had any material outside conversations in the last three months you want to tell me about?" Most CFOs at 18 months have been approached. The question is whether they engaged.
What to offer
Two things, both structural.
A concrete change the board will make. Not aspirational. Actual. "I will authorise a second-tier hire by end of quarter." "I will move the board pack cadence from monthly to six-weekly." "I will support you reshaping the audit relationship." One meaningful, specific change makes the conversation land.
A conversation about the next 18 months. Ask what they want their next milestone to look like. A promotion in scope, a business achievement, an exit, a listed listing, more equity in the next round. The strongest chairs make the CFO's next milestone as visible as the current mandate.
Both together tell the CFO that the chair is invested in keeping them, not just checking a box.
What to avoid
The two failure modes.
Framing it as a performance review. As soon as the CFO reads it as an evaluation, they perform rather than answer honestly. The value of the conversation collapses.
Overpromising. Do not offer changes the board cannot deliver. The commitment is only useful if it is real. A CFO who is offered an aspirational change and does not see it happen within a quarter will interpret the whole conversation as manipulation and accelerate their exit rather than delay it.
Why the conversation works
Most CFOs at 18 months are in an ambiguous state. They are not actively looking, but they are open to conversations. They have friction they have not articulated to anyone. They are wondering whether the chair actually values them or just tolerates them.
The 45-minute conversation resolves the ambiguity in the chair's favour, usually for another 12 to 18 months of tenure.
Compared to the visible plus invisible cost of a failed CFO transition (£1m plus for a mid-market business), a 45-minute chair conversation is the highest-return time investment a chair can make.
If you have a CFO approaching the 18-month mark and would like to think through how to structure the conversation, get in touch. We coach the specific framing directly.
