Can the seasoned pro teach the rookie?

Dear Ken Keller,

I’ve got a situation that I need some help addressing.

One of my employees has been with me for many years. He is a hard worker and knows his stuff. While he hasn’t been good about making himself better at his craft, I am OK with that because he is punctual, does quality work and works well with his fellow employees. I’ve never had an issue with him until now.

My employee is not getting any younger, and he is not in the best of health. I have no idea as to when he is planning to retire, and I am continually thinking about the risk to the company if something happens to him.

So, I’ve asked my long-tenured employee to start working with a younger guy so the younger guy can, over time, learn what he needs to know just in case something happens.

The older employee refuses to cooperate, and now I am back to square one.
—Will O.

Dear Will:

You have a problem that is happening more often than you think. It’s going to become commonplace as Baby Boomers strive to stay on the payroll as long as possible.

Unless you have had a series of discussions with your older employee about the need to start this transfer of knowledge for his benefit and to reduce the risk to the company, he may be feeling that this is some sort of betrayal and you are getting ready to give him a gold watch and send him into retirement.

This, I presume, is exactly what he is trying to avoid.

No one who works as hard or as long as you say this employee has for you is going to give up anything without a good reason. People like this are prideful of their work ethic, their knowledge and their contribution to the company they work for. It provides them with security, but what is more important is it provides them with association and stature.

You may not think this way, but your employee does.

You need to allow ample time for your treasured employee to process what you are thinking. You need to paint a picture of what his future will look like during and after this transition so he can get comfortable with what you desire to do.

How you handle this will be viewed by others in your company as a significant test of how you treat older employees who are loyal and have been contributors for many years. Take ample time and do it right by this employee.

Dear Ken Keller,

How often should I be meeting with my managers? We have a monthly staff meeting, but I don’t think that this is enough. I also meet with them informally more often.
—Pamela J.

Dear Pamela:

You should meet with each manager every week in person or on the phone and discuss their objectives, how things are progressing, what the obstacles are, and what resources and help they need to achieve their objectives.