Can I ask my boss for pet insurance?

Dear J.T. & Dale: I have several pets — my fur-babies. My company offers amazing health benefits for families. I'm not married. I'd like to see if they'd cover my pet insurance. Do you have a good way for me to ask them to offer it for those of us with pets as families? — Ellen

DALE: You bring back a memory, a case relayed to me by a friend who worked in human resources. There was a woman working in the company who was a cat lover. Then, one of her cats died. The company had a policy of compassionate leave, whereby if a member of your immediate family passed, you got time off. Well, you guessed it — the cat lover, declaring that the cats were her family, wanted paid time off, feeling that it was "only fair." Did she get it? Not a chance. Our friends in HR are obsessed with precedents and not setting them.

J.T.: But there's no harm in asking about a potential benefit. That said, it's going to be the way you present it that will dictate how much they may pay attention. I would start by quietly figuring out how many people in the organization have pets. I would then also do a little research on what pet insurance costs. Then I would set up a meeting with your boss and go over the information and ask if she or he might suggest how you could submit this as a benefit request to management. By showing the data and expressing how much you'd love to have this feature for yourself and your teammates, it will sound more attractive than saying that it's not fair that there are benefits for humans and not for your furry loved ones.

DALE: I have to disagree. I know the dead-cat story only because it was routinely told by my HR friend when griping about employee requests. It's possible to get branded as someone who is overreaching, and that can start to seem like ingratitude. My point: Before you do all the research, go to your boss or HR and ask if they'll be giving thought to new benefits anytime soon. If they seem open-minded, then you offer to do the research on pet insurance.