Originally published on LinkedIn on 15 October 2026.
The Stay Conversation
This series looks at the conversations most leaders know they should have, and don’t. This week: the stay conversation, asking your steadiest people what would make them leave, before they decide for themselves.
The blind spot
Your most reliable senior associate hasn’t raised a concern in two years. The work arrives on time, the clients are looked after, and nothing about how they operate suggests a problem. You rely on them, and you read that steadiness as loyalty. If something were wrong, you are confident they would speak up.
From their side, there may be things they’ve thought about raising. A workload that crept up, a route to partnership they can’t quite see, a decision that went over their head. Whether those get raised often depends on whether anyone has ever invited the conversation. A quiet person who delivers may rarely be the one who gets asked.
Why this happens
Two things:
Complaints are the signal leaders are used to acting on. A concern that is raised gets a response. A concern that isn’t raised gets nothing, so silence is easy to read as a sign that all is well. A person who hasn’t raised a concern may be content, or may be weighing what raising it could cost them.
Research by Detert and Edmondson (Academy of Management Journal, 2011) found that employees hold largely unspoken beliefs about when speaking up is risky, such as that it could harm their career, or that they need a solution before they raise a problem.
Those beliefs were linked to silence even when the idea was in the organisation’s interest. Someone who is content and someone who is holding back say exactly the same thing, which is nothing. Only asking tells you which one you have.
In pressurised environments, blind spots stay invisible until something surfaces. Research on urgency suggests why. In experiments published in the Journal of Consumer Research in 2018, Zhu, Yang and Hsee found that people often chose an urgent task with a small reward over a non-urgent task with a larger one, and the effect was stronger among people who see themselves as busy.
A steady associate who keeps delivering is rarely urgent, so attention goes elsewhere. The gap stays out of sight until a resignation, a missed deadline or a write-down brings it to the surface, and by then the options are narrower.
What this actually costs
The first cost is attrition. Thomas Telman’s own data puts the cost of replacing a senior fee earner at between one and a half and two times their basic salary. Most employers never put a figure on it.
In the CIPD’s Resourcing and Talent Planning Report 2022, a survey of 1,055 UK HR professionals, 72% of respondents reported that they don’t calculate the cost of labour turnover. The cost is more than a vacancy. It is the client relationships a senior fee earner holds, the matters they carry, and the months it takes to recruit and bring a replacement up to speed. A departure can arrive without warning, which leaves a firm little time to plan.
The second cost is quieter. A workload that has crept up, or a brief that keeps shifting, doesn’t disappear because nobody mentioned it. It can turn into time that never gets billed in full, which shows up as write-downs and a slipping realisation rate. When a team’s realisation rate keeps falling without an obvious cause, there may be friction nobody has named.
How to have the stay conversation
The aim of the stay conversation is to learn what keeps someone at your firm and what might make them leave. It isn’t a negotiation, and it isn’t a performance review.
Ask directly, in a one-to-one that isn’t an appraisal. Say at the start that you are asking because you value them and nothing is wrong. Then: “I’d like to understand what keeps you here, and what would make you think twice about staying.” It’s easier to answer when it’s clearly separate from a conversation about their work.
Ask what they would change. “If you could change one thing about your role, what would it be?” People will often answer a question about the job more readily than one about leaving, and the answer may point to the same place.
Listen without fixing it. Don’t defend, explain, or promise. Say thank you. Promising a fix in the room can close the conversation before you’ve heard everything. Come back within a week with one thing you will do and one you can’t, and say why.
One question to ask this week
Think of the two or three people on your team you would be most surprised to lose. Ask yourself plainly: when did I last ask each of them what would make them stay?
If the answer is never, or not for a long time, that is worth noticing.
The stay conversation is one of the most consistently avoided in professional services, and one of the most expensive when it doesn’t happen. If you want to know where operational blind spots are potentially costing you money begin with our free self-assessment. It’s your own private, confidential read which takes only 3 minutes and you will see where you are exposed and what to do next.