Bossy Britches: So Your Secretary is Cute, Now What?

A "little crush" might be crushing your leadership
A "little crush" might be crushing your leadership

A Little Intro

So here it is. You've made it into a leadership position within your company and you get all the responsibilities that go with it. Fun? Sure. Challenging? Always. Within the experience and training you've attained throughout your professional career, you've become confident and knowledgeable in your profession. If nothing else, you're in charge. By now, it should be common knowledge that leaders and managers get their fair share of "schmoozing" from those who consider themselves subordinates. In fact, you've probably seen it your entire life. But what responsibilities do you have to those that "LIKE, like" you (or at least flirt)? Whether you are a man or woman, the principle remains the same. Here's the "why" and "how" of navigating this unique workplace relationship with graceful professionalism.

If you're on the opposite end of the spectrum and you're boss is crushing on you, you may be interested in an article I wrote for, Bossy Britches: How to Cut Your Boss's Crush (...and not get fired)

The "Why"

A little flirting never hurt anyone, right?

I get it. It can't be that bad for you, her/him and the company to show someone a little more attention, right? Unfortunately, that's just a lie you tell yourself to justify the fun involved in having an office crush. Looking more objectively at the scenario will quickly display the flawed thinking that typically accompanies those who choose to engage in these behaviors. First, you must address what should be the most obvious issue...favoritism. If you believe the others around the office haven't noticed that you've taken a liking to that certain someone, you're absolutely wrong. Showing favoritism to any employee will cause the others to not only feel less important, but also to question your decision-making ability. The office will start to make subtle comments to each other, questioning your objectivity. For example: "Of course the boss sent her to the event, she's got him wrapped around her finger." How much respect and faith will your co-workers and employees have in someone that they believe is so easily persuaded by perfume?

Decreased Efficiency

It should be no question that efficiency can quickly be affected by nearly everyone involved in an office crush, including your own. It could be as simple as taking more coffee breaks than usual just to chit chat with that special someone -OR- it could become as monstrous as making compromises with deadlines for yourself AND your special friend. Looking outside the immediate relationship dynamic, a loss of morale within the office caused by favoritism will very certainly translate into lost motivation, output and efficiency on the part of everyone else. I can't over state enough, the importance of developing a meaningful personal connection with all your subordinates, but you must always be sure to guard yourself from crossing the line into publicly obvious favoritism, or you can watch office morale melt away just as quickly as the motivation and efficiency that once existed.

The Danger of Disregard

The temptation to take this all too common issue for granted is almost always high. Perhaps the most comfortable decision you can make is the one that allows you to convince yourself that an office crush is "no big deal." Consider the situation more objectively; however, and you might just find that nearly every personal and professional meltdown, fueled by a scandalous affair, started exactly the same way - with a nonchalant attitude. Even our 42nd President, Bill Clinton, will likely tell you that when the inappropriate relationship began, he didn't see it as a threat.

For the sake of argument, let's just say that it may not be that big a deal. Let's assume the relationship will never evolve into a life altering monster and will only ever be a simple office crush. Can you say with certainty; however, that it will never affect your decision-making ability? Can you state with absolute authority that organizational morale will never be affected? What real benefit is derived from the "innocent" exchanges? There is only risk of a negative outcome, and likely zero chance that the behavior will positively impact your company. Managing these relationships with professionalism will certainly be beneficial to you and your organization, but disregarding them as "nothing" has no chance of helping you develop a world-class organization. All the risk lies in disregard, with absolutely zero long-term reward for your organization.

The "How"

Placing Social Boundaries without Getting Weird

You get it. You understand why these relationships have to be intentionally managed, but how do you fix it without creating a permanently awkward working relationship? What if he/she quits? What if I confront the issue boldly and they act like they have no idea what I'm talking about? Won't I just look stupid and unprofessional? The answer to all these questions lies in a single word, subtly. You see, in a sense, you're fear is absolutely correct. To avoid the embarrassment of rejection from the opposite sex, your office crush will very likely pretend they have no idea what you are talking about if you confront the issue directly. In fact, they may even speak with HR about your unwelcome advances, just to preserve their own dignity in the face of absolute rejection. Even worse, they may not be pretending, actually having no clue that you had a serious crush on them and that they were unintentionally fueling it.

Subtly. "So slight as to be difficult to detect or describe; elusive: a subtle smile." (

Although the idea of applying subtlety on paper seems difficult, a little preemptive planning will set you up for success as future situations arise down the road. Understanding how to specifically handle the scenarios that often play out in the workplace will give you the confidence and ability to act appropriately. These tiny "moments" that occur on a daily, or at least weekly basis will be the deciding factor on which direction your relationship will take from now on. Using the basics of subtlety, you have to understand that others will likely conclude the same things you would, if the roles were reversed. For example, your crush walks into your office (as they normally do) to sit down and chit chat with you about office politics. After making your initial and polite greeting, allow them to talk while you continue to "work" on other tasks. If your lack of full attention isn't enough to urge them back to work themselves, a simple, yet subtle statement of "I have a lot to take care of, before I dive into this, is there something that I can help you with?" Watch closely, as the realization that your priorities have shifted sets upon them.

Play the "What if" Game

A thousand scenarios could play out, obviously. You might be thinking "they are more persistent than that" or a host of other worries. The concept remains the same. Think ahead. Consider the little "moments" that often occur at work that so often encourage the crush, and decide beforehand exactly how to handle them professionally and politely. They like to joke with you in the break room? Make a quick joke back, or just chuckle politely, get your coffee and head out the door. They like to send you personal (non-productive) emails? Send back a "lol" or just don't respond. A little subtlety goes a long way to quickly show them that you're not interested in an unprofessional relationship (anymore). If you are in the opposite position and your boss just won't let go of his crush on you, stay tuned for my next article on how to break your boss's crush without losing your job.

A leader makes the best decision for his organization, not his ego.
A leader makes the best decision for his organization, not his ego. | Source

Quick Tips

- Put pictures of your wife, husband and kids (or significant other) on your desk to demonstrate your love and dedication to your family.

- Never talk about your significant other negatively at work. Never. You may be creating ideas of opportunity to those around you who subconsciously wish to fill those "needs" in your personal life that they believe are not being met.

- Don't ask women about their husband and boyfriends when building morale (especially if you believe they are attracted to you). Conversely, women shouldn't ask men about their wives. Instead, ask about their "family" and let them decide what that means.

What Do You Think?

Do you think leaders should be more intentional about managing "flirty" relationships?

  • Please God Yes!
  • I can see the benefit. Also I'm not easily excitable.
  • No. Leaders should flirt with their subordinates like they are in college.
See results without voting

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