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Employee Termination: How to Fire a Friend (Gracefully)

Employee Termination: How to Fire a Friend (Gracefully)

By: Ronald Shapiro, author of Perfecting your Pitch (Penguin Group, 2013)

Managers sometimes have unique relationships with different members of their teams. Most, if not all, hopefully fall on the positive side of the ledger. Some may even lead to close friendships.

As a result, a manager may find himself in a bind if he shares a close bond with one of his charges who is underperforming and lacks the ability to improve.

How to Manage a Termination
It can become awkward if after trying to steer the employee to a better track the manager determines that his friend must be terminated for the good of the company. The uncomfortable task then requires communicating the termination with the hope of minimal damage to the personal relationship.

A manager’s explanations may not be sufficient to overcome the employee’s hurt feelings and preserve the friendship. But a script with a clear message may salvage a valued relationship.

The message should express a willingness to give advice as the terminated employee seeks other opportunities and — assuming the manager can candidly support it — offer to write the former employee a recommendation.

No matter what the manager says, the terminated employee may only hear “termination” and effectively shut down conversation.

You might then try to reopen a constructive dialogue with questions — “Do you understand why I’m saying this?” or “Do you have any questions?” Questions may help kick-start dialogue and open channels of communication.

Writing a Letter of Termination
As a teenager, I worked as a lifeguard at a pool in Philadelphia. One afternoon, I saw a seven-year-old boy and his younger sister sitting tearfully in the lobby of the swim club. I approached them and learned that they had just been informed of their dad’s sudden passing due to a heart attack. I took the boy, Ryan, under my wing that day and for the next five years was his “big brother” until I left for law school.

Years later, we were reconnected when my law firm’s hiring committee picked him to work in our corporate law department. Subsequently, due to a consolidation in the department and some economic changes — as well as his lack of experience in certain specialties for which the firm needed personnel — Ryan had to be terminated.

As a result of my close bond with Ryan, I decided that I would communicate to Ryan the firm’s decision. As I was jotting down some notes, I knew that I wanted to let Ryan know that, despite the conclusion of his employment, my affection for him continued and to assure him that I would be there for him in the future.


Our lives have been intertwined for a number of years. I view our relationship as special and your coming to the firm was a happy occasion for me. So telling you that your work here will have to end soon is not easy for me. The economy and the scope of your practice capabilities dictate that your position will be eliminated. As of sixty days from now, you will no longer be associated with the firm. That is a difficult message for me to deliver to you.

But I also want you to know that during this remaining period, I and others here will support you as you look for other opportunities and we will also provide you with six months’ severance until you find a job in the event your search takes longer than the sixty days.

I suspect you are overwhelmed by the news. Do you have any questions? [Listen carefully and respond.] Please remember, I view you as family, and just as I would tell any of my sons I tell you— when the shock of the decision subsides some, come to me for advice, references, and whatever other support I can give you.

Is there anything else I can explain? Would you like to have lunch tomorrow after you have had some time to digest this?

Forty-five days following our meeting, Ryan left the firm. He took a job in the corporate law department of an entertainment company. After a decade of hard work, he rose to the top of the company’s legal department and then moved to its executive suite. On my desk now sits a plaque commemorating a donation in my name that he and his wife made some years later to support a scholarship for at‑risk children.

When terminating an employee, especially one who is a friend, keep in mind:

  • Use the two key elements of this situation — acknowledging the importance of your relationship and the finality of the decision — as a guide when scripting this message.
  • Devote time practicing delivering the message to reduce discomfort.
  • Be prepared for an emotional response and possibly a significant short-term change in your relationship with the former employee.
  • Ask questions and express concern to restart the dialogue.
  • Allow time for responding or venting.
  • Make sure to follow up on that lunch.


From PERFECTING YOUR PITCH by Ronald Shapiro. Reprinted by arrangement with Hudson Street Press, a member of Penguin Group (USA) LLC, A Penguin Random House Company. Copyright © 2013 by Ronald M. Shapiro.

Author Bio:
Ron Shapiro
, co-founder of the Shapiro Negotiations Institute, has negotiated more than $1 billion in contracts. His techniques have helped resolve a national symphony orchestra strike, facilitate solutions to human relations problems, and reconcile disputes in the government and corporate world. His New York Times bestselling books include The Power of Nice and Dare to Prepare.