We are a 30-agent real estate brokerage company with one administrative assistant, our lone employee. She has been with us for more than 30 years and is loyal and cheerful, and always answers the phone with a smile. However, her professional abilities have not kept pace with the times. She has no technical skills and can’t keep up with her other tasks. She is 75 years old and we are at a loss regarding how to handle easing her into retirement.

This is tough, because she’s a long-term employee who has done great work. If she was someone you hired two months ago, I’d say it’s time for a “it’s been great, but here’s the door,” conversation. That won’t work here.

And the age thing makes it a bit more complicated. Whoever you hire to replace her will be younger (almost assuredly) and you don’t want it to look like age discrimination — because it’s not. She simply can’t keep up with her other tasks.

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You may ask why you can’t just say, “Jane, you’re 75. Are you thinking about retirement?” You can, but you need to do it correctly. If she says she plans to work up until she dies, you have to take her at her word. You can say, “Jane, you’ve been here 30 years and I’m surprised you’ve put up with us for that long. Do you have any plans to retire?”

If she indicates that she has been thinking about retiring, then you can address a timeline or talk about working reduced hours. But if she says she has no interest in retirement and then you jump into performance issues, it will look an awful lot like you want her to retire and are just making up issues to get her out the door. So I’d skip the retirement talk and start with the performance issues.

Speak to her directly: “Jane, you are awesome at answering the phone and the clients love you. But, we also need X, Y and Z done. What can we do to help you learn these tasks?”

Now she may say, “Oh, if I could have a formal email training class that would be great!” Or she may say, “Oh, I could never learn to do that fancy technology.”

If she says the former, then you send her to the email training class and your problem may be solved. While learning new things does become more challenging as our brains age, it’s certainly not impossible.

If she says the latter, however, you have your opening. “Jane, I know it’s hard, but it’s a critical part of your job. We’re willing to do whatever it takes to help you, but you need to do this.”

Document all of this, of course. If she refuses to learn or tries and fails, then you can put her on a formal performance improvement plan, otherwise known as a PIP. If she doesn’t meet the criteria after 90 days, you can terminate her.

On the other hand, if she really is great on the phone and she’s cheerful and loyal, those are harder skills to find than someone who can do the other side of the business. Have you considered splitting the job?

You can do this two ways. One, you can hire a second person to take over those tasks your current administrative assistant can’t handle. The upside of this is you get to keep your long-time employee with great people skills and you get someone who can carry out the more technical aspects of the job. The downside is now you have two salaries to pay. That’s a big bite out of your profits.

Or you could propose a job share. “Jane, we really need someone who can do X, Y and Z and it’s clear you’re not that person. Would you be interested in working part-time while we hire someone else part-time to do these other tasks?”

She may jump at that chance. It’s quite possible she would like to work fewer hours (although she may not; I admit to using stereotypes here). It’s quite possible that she’ll feel relief at not being pressured to learn new things she has no desire to learn.

She may say no, that she’s perfectly happy with how things are. In which case you have to go back to being the bad guy who says, “You have to either learn to do these things or we’ll have to let you go.” And it’s back to the PIP.

This is harsh and unpleasant, and an action you may not wish to do. You may wish to suck it up and work around her until she decides, on her own, to leave. I can’t make that judgment for you. Ultimately, you need to do what is right for your business, which might mean showing a bit of compassion to a loyal employee. Remember, everyone else in your business is looking at this as an example of how they will be treated. 

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