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Chapter 4, First the Team

How should a leader let someone go?


The leader holds the conversation privately and in person, keeps the reasons about fit rather than failure, offers real support into the next role, tells the remaining team with discretion, acts promptly rather than letting it drag, and stays in the relationship afterward. The team watches the departure as closely as it watched the hire.

Letting someone go is the leadership practice the operators I interviewed talk about least and feel most. Some hires turn out to be the wrong fit through no one’s fault. Some people underperform persistently and cannot be coached up. The leaders who have handled this well told me the goodbye is the truest test of their posture toward the team they have built, because the people who remain are watching every step of it.

The first discipline is framing. The late Patrizio Cipollini, general manager of Four Seasons Hotel Firenze, watched many colleagues who had grown up under him move to other Four Seasons properties around the world and into very senior positions. He described the feeling without pretending it was easy.

“I am very proud of them and am grateful that they had the chance to grow with us first.” Patrizio Cipollini, general manager, Four Seasons Hotel Firenze

The leaver is a graduate rather than a defection. That framing is what makes a dignified parting possible, and it is also what sends the kind of word back to the property that becomes, over time, its most reliable recruiting channel. The same posture applies when the departure is the leader’s decision rather than the employee’s.

From there, the leaders I interviewed describe six practices in common. The difficult conversation is held privately and in person, by the leader, never delegated to a more junior manager. The reasons are made clear without becoming personal: this role is no longer the right fit for what the operation needs, rather than you have failed. The support into the transition is real rather than performative, meaning references, severance, time to find the next role and an introduction to operators who might be hiring. The team is told, with appropriate discretion, what has happened and why, in language that does not undermine the departing colleague. The conversation happens promptly. And the leader stays invested in the relationship after the working tie has ended.

The point about promptness deserves a closer look, because it is where most leaders fail. The team can usually see for months what the leader is reluctant to acknowledge. Every week the gap drags on, the colleague’s continued presence corrodes the standards of the people working alongside them, and the right hires begin to resent carrying someone who is not pulling their weight. That resentment, accumulated, eventually pushes one of the right hires out the door. Delay feels kind. It is not.

The continuing relationship is the practice that distinguishes the best operators. Recommending a departing sous chef to a chef across town who is hiring. Taking the call six months later from the former front desk supervisor who is stuck in a difficult conversation at their new property. Over a career these relationships build one of the most durable professional networks the industry can produce, and they tell the team that remains something important about how they will be treated if their own time comes.

Temperament underwrites all of it. Jonnie Boer, chef and co-owner of De Librije in Zwolle, put every applicant on trial in his kitchen for a few days, and his description of how he ran those days applies just as well to the hard conversation at the other end.

“I believe that people perform better when they are treated well, so I always stay calm, take everything step by step and maintain a birds-eye view.” Jonnie Boer, chef and co-owner, De Librije, Zwolle

A departure handled with that calm is one more act of leadership by example for the people who stay. It tells them this is an operation they can give themselves to without fear. A departure handled badly teaches the opposite lesson, and the team, having learned it, adjusts accordingly.

Chapter 4, First the Team, sets the dignified departure alongside hiring for character, onboarding, culture and the leader’s role as protector of the people who report to them.