Are Your Employees About to Join the Great Resignation?

Conversations to have with employees at least once a year to head off surprise resignations.

It can come as a great surprise when an employee, whom you thought was happy in their job, tells you they are leaving. I wanted to find out if there were conversations you could have with employees at least once a year to head off a surprise resignation.

I found this article on the Harvard Business Review Website by Christopher Littlefield that offers conversation-starter questions. Here are several:

  • How have you been feeling about work in general?
  • What part of your job are you enjoying the most?
  • What aspect of your job do you enjoy the least?
  • How have you been feeling about being able to balance work and home?

If I were asking an employee these questions, my concern would be that they answer honestly. To find out, I would try asking follow-up questions. For example, if they say in response to the first question about how they feel about work in general, that “it’s great,” I would drill down and say: “I’m glad to hear that! What makes it great? What are examples of some of the great things about your daily routine with us?”

It wouldn’t be hard for me to answer that question because my personality tends toward introspection and self-expression. Some people, however, have personalities that are not analytical, especially about their own feelings and thoughts. If the employee is at a loss for words, I then might say: “Well, what’s a typical day like for you?” You might get clues about overwork or boredom that way. The employee might tell you they usually wrap up work by around 7:30 p.m. or 8 p.m. most days. With some employees still working from home, and others on a hybrid model with just a couple days per week in the office, quitting time each day probably has been extended. With the time for the commute removed, additional work time may have filled the void, so that rather than turning off the computer at 5 p.m. or 6 p.m., as they did when they were commuting, some employees may find they are struggling to enforce a quitting time of 8 p.m.

“You certainly are making the most of your time working at home,” you might say, “but I want to make sure you are not, ironically, working even longer hours now that you’re home. Even though we no longer go to the office every day, it’s still important to enforce a reasonable quitting time each day, so you have time for yourself to refresh and re-energize.”

A clue to an unmanageable workload can be unused vacation days. If you notice that in the previous year the employee had a week, or more, of unused vacation time, it’s worth having a conversation about it. “I noticed you had a lot of unused vacation time last year. Was there a work-related reason that you didn’t take that time for yourself? What is your schedule like in the days leading up to a vacation?”

“It’s torture for me to take vacation time,” I once said to a manager. “I have to do so much work ahead of time that I sometimes have to do work two weekends beforehand and work until 11:30 p.m. every night the week before to make sure everything is in place for when I won’t be there.”

What is a good response to such a statement? “I’m glad I asked, and that you were honest with me,” I would say to an employee. “Let’s see what we can do to make it easier for you to take time off. You should be able to use all, or almost all, of your vacation time every year. If you don’t use all of it, it shouldn’t be because of your workload.”

One way to make it easier for an employee to take time off is hiring a junior employee, even if only on a part-time basis, to lessen the workload and pick up the slack while the employee is away, reducing—or even eliminating—the need for work to be done ahead of time. Another solution is finding weekly deliverables that can be eliminated or assigned to another employee, who has more time or already has a junior employee.

Asking an employee whether they feel like they are continuing to learn new things may be a good way to head off an employee leaving due to boredom and lack of fulfillment. If you ask an employee if they are “bored,” most will not be honest with you. If they tell you they are learning new things, ask for examples of things they learned over the last year.

Happiness is just one factor deciding if an employee stays with you. Unfortunately, another important factor is money. I know this because there are many jobs I would love, but simply cannot afford to take. If you have an employee whose business unit is profitable, maybe even highly profitable, and their salary is a real steal for the company—in other words, a person you know you’re under-paying—don’t wait for that employee to ask for more money. It’s hard for many people, especially women, to do that. Be proactive, and offer a merit-based increase that goes beyond a standard cost-of-living adjustment. You may think you’re getting away with something by not paying the employee as much as you know you should, but when a mission-critical employee gives you their two-week notice, you won’t feel so smart.

What questions do you train managers to ask as conversation-starters to gauge how likely it is that a high-performing employee will stick with you?