Convincing a Millennial to keep her job


(MoneyWatch)Dear Evil HR Lady,

Any thoughts about how to convince a Millennial to stay in a perfectly good job? My sister is 25, and she has a really "awesome" pattern of employment -- get a job, stick around long enough to get insurance and quit.

I think that in the millennial brain, there's motivation in having a job to gain insurance. But once gained, the motivation is gone. She has health issues and requires regular health care, so she pays for COBRA between jobs. Now she's in a good job with health insurance and is pregnant and still contemplating leaving her job. What can I say to her?

"Please pass the mashed potatoes," comes to mind. Because that will at least get you mashed potatoes, which happen to be delicious. Anything else you say will likely go in one ear and out the other. Little sisters, of any generation, tend to think their older sisters are being ridiculous. (I say this as a little sister.)

But on the off chance that she will actually listen to you, instead of telling her what to do (stay in the job, duh!), ask her a question. Or rather, ask her a bunch of questions. If you can make it sound like casual conversation, all the better. Here are two questions to get your started:

"What would make you happy in a job?"

"Why do you think the next job will provide that?"

And then listen to her answers. If she's after the challenge of getting a job and/or getting insurance and then feels let down after achieving that, what she needs is to identify a challenge in her current job. Even if that job is flipping burgers, the next challenge is to get moved up to cashier, then shift coordinator. If it's an office job, there's always a task that can be done more efficiently, a coworker who needs to be trained, a boss who needs to be understood, a promotion that can be gained, a stellar performance rating to be earned, or a year-end bonus to strive for.

She's neglecting to see the challenge in staying in the job she has and making that worthwhile. And she's underestimating the increasing difficulties she's going to face going after the next job. When someone is young, their resume is typically full of short term jobs because of school schedules, internships, summer jobs, and the like. But, as more and more of those short term jobs pile up, the harder it is to find the next job.

The better the job, meanwhile, the less likely the manager is to want to hire a job hopper. Lots of people (even lots of her peers) are willing to take a job and stick to it and work their tail off. And managers would rather hire that person than the person who left her last 3 jobs after 3 months.

And then, let's talk about the baby. Here is a super good (obnoxious) question for a big sister to ask:

"Do you think it will be easy to find a new job when you're visibly pregnant?"

Because the answer to that is no. It is strictly illegal for people to consider a pregnancy as part of the hiring decision, so people will not say, "Gee, you sound great, but since you're pregnant, no." Ideally, no one would even notice, but we, here at Evil HR Lady Central deal in reality, and the reality is that when the manager has 10 resumes on her desk and every single one of those people could do the job, then the pregnant woman is going to be last choice.

Why go through the hassle of teaching and training her when she'll be out on leave four months down the road? If she's outstanding and better than all the others, she will be hired, regardless of pregnancy status, but with that job-hopping thing that's enough to beat any legal challenge right there. No lawyer would even touch her case, and every hiring manager would say the same thing: "I'm looking for someone capable of a long-term commitment, and since she left her last three jobs in less than six months, she was not the right fit for our organization."

Of course, since we're dealing in realities your sister probably won't listen to a thing you have to say. But if she is willing to listen, then I'd definitely help her find ways to set goals and accomplish them within her current job. That can give her the thrill of the chase without the permanent damage to her career.

Have a workplace dilemma (or an annoying sibling)? Send your questions to