Should I try to convince someone to stay?

It’s a common management situation: someone walks into your office, and says “I think I’m leaving.” The next move is yours, and it stumps a lot of managers. Should you:

  • Try to talk them out of leaving
  • Beg and plead for them to stay
  • Wish them the best of luck in their new job
  • Advise them to be careful of the door on their way out

Of course, your answer is highly dependent on the situation, the person, and the timing. If this is a crucial position, and you’re within weeks of a crucial deadline, you will respond differently than if it is a loser who you’ve been trying to figure out how to handle for months. So I can’t give a single, pat answer for every situation. But I can tell you how to approach the decision.

Are they special?

First, you need to ask yourself honestly how important this person is to your organization. And here, it is important to differentiate the person from the position. Right now, it’s all about the person. (We’ll assume for the moment that this is a position the organization really needs.)

If this is someone you can see in almost any position, then they are worth saving

If this individual is quite special, someone you can see in almost any position in your organization, then they are worth saving. If they are good, even if they have years of experience, but not truly special, you should probably just let them go.

This is the crucial choice, the one that deserves the most attention. And you need to be very self-critical on this. Are they honestly unique? Or can you imagine finding someone as good within weeks? This is the crux of the decision, but if you are honest with yourself, it’s not that hard to make.

Why are they leaving?

Assuming they are worth saving, you should place yourself in the other person’s head, for just a minute. Ask yourself how hard this decision was to make, and how difficult you think it was for them to tell you. If you think this was a very big decision for them, that they anguished over it for weeks, and they have been dreading coming to tell you, you need to take that into account. In such a situation, trying to talk them out of it will only make them feel worse, solidify their decision, and make you look desperate.

How you approach this conversation is critical

If, on the other hand, you think they just got an offer and decided quickly to take a shot at it, perhaps you do have a chance to convince them otherwise. How you approach this conversation is critical. If you are flippant or ridicule the other opportunity, you are essentially telling them how stupid they are for considering it. Not a good approach.

If you are calm, reasoned, and considerate, you may have a chance to convince them to stay. You need to move into “trusted advisor” mode, and try to help them evaluate the choice. This is your only chance to change their mind. If you become someone they can trust, and rely on to be objective, maybe they will want to stay. It’s a slim chance, but well worth a try. And if it fails, you still have credibility — and perhaps they will return when the grass isn’t that much greener over there.

Is it a ploy?

Quickly wish them well, and offer to help clean out their desk

Another possibility is that they are threatening to leave simply to gain concessions from you (more compensation, for example). If this is the case, you need to call their bluff. Quickly wish them well, and offer to help clean out their desk. If it is a ploy, it speaks volume to their character, their dedication, and their relationship with your organization. You don’t want/need them.

If they are willing to leave on those terms, what will happen when the going really gets tough? And if you cave, what’s next? Will you offer them your job to stay? No, just let them go, and send a clear message to all in the organization that this behavior is not condoned.

Can you afford it?

Finally, if you find yourself needing to make some kind of committments to keep them (more money, fewer hours, new manager, etc.) you need to do so very carefully.

You may end up with a parade in your office

First, be sure you can actually deliver. Nothing could be worse that for you to convince someone to turn down another offer, and then not follow through on your part. They will never trust you again.

Second, be sure it is something you are willing to do for similarly placed individuals. Word will get out, and you may well end up with a parade in your office looking for the same concession. This is another reason to be sure the person is truly special before you make the decision to convince them to stay. That way, you can differentiate when the others come marching in.


I’m a “thanks for playing our game” kind of manager

In summary, the important decision is the uniqueness of the individual. If they are truly special and unique, try to save them. Otherwise, simply let them go. And if you want to save them, it’s vital you understand their motives, so you can best change their mind. In general terms, I’m a “thanks for playing our game” kind of manager. Special people just don’t come around that often.