How do I let go of someone who has worked for my family for 20 years?

To let go of someone who has worked for your family for 20 years, first be sure the decision is right and the alternatives were tried. Bring in HR and employment counsel early for the legal side. Tell your parent before anyone else knows. Then have the conversation yourself, in person and clearly, with real respect for what they gave, and protect their dignity in how the team is told.

This is one of the decisions that defines a successor. The company will remember less about the decision itself than about how it was handled.

Why is it so much harder in a family business?

A long-serving employee in a family company is rarely just an employee. They may have joined when the business was small, worked beside your parent through the hard years, and known you since you were a child. Some will have been to family weddings. Their loyalty was often to the founder personally, and the founder’s loyalty to them was real.

So the decision carries weight beyond the role. The rest of the company will read it as a signal about what the new generation values. Your parent may feel it as a judgement on their own loyalty. And you may feel you are breaking an unwritten promise the family made long before you were in charge.

None of that means the decision is wrong. It means it has to be made carefully and carried out well.

Is it the right decision?

Before anything else, be honest with yourself about why.

Is it performance, or is it fit with the future? Both can be valid, but they lead to different conversations and different alternatives.
Have they been told clearly what is expected? If someone has never been given honest feedback, letting them go without it is unfair, and often legally risky.
Is there a different role? Some long-serving people are in the wrong seat rather than the wrong company. A changed role, a smaller remit or a defined path to retirement can be the better answer for everyone.
Are you acting on your own judgement? Make sure this is not about wanting to show you are in charge, or about someone who disagrees with you. If the real issue is that they resist your leadership, read when a senior executive pushes back in public first.

If you are not sure, wait and gather more evidence. If you are sure, do not let the history make you delay for years. Keeping someone in a role they cannot do is not kind to them or to the people around them.

Who needs to be involved?

HR and employment counsel, early

This article is about the leadership and human side only. The legal side, including notice, severance, documentation, any agreements and the process the law requires where you operate, is for your HR lead and an employment lawyer. Involve them before you have the conversation, not after. Long service often changes what is required and what is fair, and getting it wrong can hurt both the person and the company.

Your parent, before anyone else

Your parent should not hear about this from the person, from a colleague or from the grapevine. Tell them yourself, privately, before the decision is final if the handover agreement gives them a say, and before it is announced in any case.

Explain your reasons plainly, with the evidence, as you would to the board.
Acknowledge what this person meant to them, and that the decision may be painful.
Ask how they would like to be involved. Some founders will want to speak to the person themselves afterwards. Some will want to stay out of it entirely.
Agree in advance that they will not reverse it. If the person goes to your parent afterwards, as many will, the founder’s answer has to support the decision. Otherwise the whole company learns that your decisions can be appealed.

If your parent disagrees strongly, you have a harder conversation to have first. Our article on how to disagree with your parent in the family business covers it.

How should the conversation go?

Have it yourself. Delegating it to HR or to another manager, when the person has given decades to your family, will be remembered by everyone. HR can be in the room if your advisors recommend it.

Prepare it, word for word

Write down the first two or three sentences and rehearse them. In a difficult conversation, people tend to talk around the point for several minutes before reaching it, which is harder on the other person, not easier.

Say it early and clearly

Within the first minute. Something like: “I have made a difficult decision. Your role is going to end. I wanted to tell you myself, and I want us to talk about how we do this well.”

Then pause. Let them react.

Keep the reasons short and honest

Give the main reason in a sentence or two. Do not reopen every disagreement of the past year, and do not invent a softer reason that is not true. If the decision is final, do not let the conversation turn into a negotiation about whether it should happen.

Recognise what they gave

Say it specifically and mean it. What they built, the years they carried, what the company would not have without them. This is not to soften the decision. It is because it is true, and they deserve to hear it from a member of the family.

Explain what happens next

The practical points your HR lead and counsel have prepared: timing, support, what will be said to the team. People in shock remember very little, so follow up in writing.

How do you protect their dignity?

Long-serving people care deeply about how they leave, sometimes more than about the terms.

Let them help decide how it is told, where that is possible. Some will want to tell their own team first.
Give them a proper farewell, if they want one. A dinner, a gathering, a few words from the family.
Never let the reason become gossip. Say less, not more.
Keep the door open where it is sincere: a reference, an introduction, a call to check in after a few months.

How do you tell the team?

The team will be anxious, and some of them will be wondering whether they are next.

Tell them quickly, ideally the same day, before rumours fill the gap.
Be brief and respectful. Thank the person by name for what they contributed. Do not explain the reasons in detail.
Say what happens next, who covers the role and when there will be more news.
Speak in your own name. Not “the family decided” or “my father agreed”.
Be available afterwards. Some people will want to talk privately. Long-serving colleagues in particular will be watching how you handled it.

Our article on keeping long-serving executives through succession covers the wider question of how to hold on to the experienced people you want to keep.

In short

Be sure the decision is right, and that clear feedback and alternative roles have been considered.
Involve HR and employment counsel early for the legal side, and tell your parent before anyone else.
Have the conversation yourself, say it in the first minute, give a short honest reason and recognise what they gave.
Protect their dignity in how they leave, and tell the team quickly, briefly and in your own name.

Hard conversations like this one are rehearsed in advance in the Second Chair™ method, using the real situation the successor is facing.