Flirting with an employee is dicey for several reasons. It often creates an unfair power dynamic, interferes with the usual pattern of success based on merit, makes other employees uncomfortable, and exposes you to the possibility of legal or disciplinary action, including termination.
In most situations flirting is a subtle and indirect way of letting someone know you’re interested. She is usually free to respond in a way that either indicates her interest or lack thereof. When you’re her boss, however, flirting with your employee places her in an awkward position, whether or not you intend for this to happen. She may feel like she can’t reject you because you could make her life difficult at work or even have her fired. On the other hand, she may feel obliged to reject you for fear of being seen as someone who would flirt her way to the top or take advantage of her sexuality instead of her knowledge and skills, even if she might actually be interested in you.
Ideally, success at work comes from a combination of knowledge, experience, skills, and results. In reality, how well someone gets on with his superiors and co-workers is also a factor. Although some see friendly flirting as an acceptable way to network, others see it as undermining the meritocracy (even if it never existed in reality). Not only can it frustrate employees who may wonder why they’re working so hard if it all it takes to succeed is to flirt with you.
Offices are prefect environments for gossip to spread. There is little privacy and people are often looking for drama as a way to combat boredom and liven up their days. Most people love a good scandal and many others love to hate people more successful than they are, so passing on word that something’s going on between you and an employee is a juicy treat (even if it’s not true). It paints both you and the employee in a bad light. You are seen as using your power to flatter your vanity at best and as committing sexual abuse at worst, or at least as being weak and easily manipulated. She is either a pitiable victim of your abuse (hardly someone you’d want to see promoted) or as a tramp who uses her body to make up for what she lacks in skill and intelligence. It’s best to refuse to engage in any flirtation with an employee.
If these other possibilities don’t worry you, this one should. Most companies have some sort of policy regarding sexual harassment and relationships between employees. Being suspected of taking advantage of an employee or of dispensing favour as a result of flirtation or even in exchange for sexual acts is not a position you want to be in. You can face all sorts of embarrassing disciplinary action or your employee can take legal action against you.
If one or both of you are married or in a committed relationship, you are in danger of being exposed to your partners. And any employee who is displeased by your perceived favouritism can send an anonymous letter to your wife or girlfriend explaining what (she thinks) is going in, a revelation which, true or false, could result in divorce.
If you still insist on flirting with your employee, keep physical contact to a minimum. Don’t say anything you wouldn’t say in front of your partner. Smile, make eye contact, tease her about being the office troublemaker, tell her you appreciate the extra hours she put in on the inventory report, but don’t say, write, or do anything explicit. Even if she appears to be interested, there can be no way to tell if she’s playing along out of a perceived threat to her employment or if she’s hoping to flirt her way to a promotion, so tread carefully or you might find yourself in a world of trouble.