Uncomfortable About Boss and My Associate’s Closeness

Question to Ask the Workplace Doctors about boss and new associate’s growing friendship:

Hello Doctors – I am a mid-level manager for a small department within a large organization. My department has another associate who just started a couple of weeks ago. I haven’t determined whether she’s aware of her growing friendship with my boss, but it’s only a matter of time. We can work relatively independently, though regular interaction is beneficial for the productivity of the group.  I have an uncomfortable problem. I’ve been working for my company for quite some time. My boss has almost always shown me great respect and camaraderie. This new associate is now my direct report. She also has a good relationship with the boss. They are quite close and communicate outside of work. Since I’ve become manager, I have learned that my direct report was given a raise as a way to boost self esteem and do better work. I also know that details I’ve told my boss have been discussed with my direct report. They will comment on my upcoming vacation or a personal experience, even though I haven’t mentioned it to them yet. While I don’t mind them knowing about these details, I feel it is my responsibility to tell them. And I’m becoming increasingly uncomfortable with their friendship. I can’t really quit or look elsewhere right now, so I’m hoping you might have a few suggestions about how to navigate this.


Dear Uncomfortable: Thank you for sending a bit more about your place of employment and your position of manager of a small group.

I sense that you value privacy and therefore are frustrated about what is going on about you. The brief description you present suggests that you are uneasy about what appears to be a growing closeness between your boss and a woman who directly reports to you, so much so that you have thought about changing workplaces although that is not suitable just now. The indicators of your discomfort are

  • “They are quite close and communicate outside of work”
  • The boss has given her a raise and
  • They discuss your coming vacation and a matter you feel is personal.

The value of submitting a question and getting advice we is give is that it helps you reflect on what’s involved. Of foremost value is your effort to clarify what motivates you to seek outside perspective. We trust you will understand our advice is not a quick fix as to what you should or shouldn’t do.

You don’t say how you know any of these things–about boss/associate growing closeness nor do you say if the boss bypassed discussion with you about raising this woman’s pay. You do say your boss shared information you gave him with this associate. I assume you’ve observed their growing interaction and/or that one or both of them have mentioned the raise and/or you overheard them discussing your vacation and some matter you feel is personal.

Most often matters of pay and closeness of those in your work area are learned by observation and hearsay and then are interpreted silently. It is only when somethings seems unfair that they become topics for gossip or confrontation. I expect you have considered what are your options. From this distance I see several that you might initiate:

  1. –continue as is and bite your tongue until and if something interferes with doing the jobs to which you and/or associate are assigned.
  2. –seek advice from someone far removed from your work situation so as to keep this matter private.
  3. –look for a transfer within your organization rather than job hunt.
  4. –express your discomfort to your boss about the growing closeness of him and this woman who reports to you and him giving her a raise without input from you.
  5. –request a meeting of the three of you to set forth your concerns and come to an agreement about do and don’ts of communication and workplace relationships.
  6. –scheduling a meeting with your work group to hammer out do and don’ts of workplace communication–topics relevant to what you are paid to do and what is inappropriate on site and outside.

What option or combination of options you elect, of course, must be weighed in light of your own career. You don’t say how well you like your job and workplace, but that your boss has treated you with respect and that you have worked there for sometime.The fact you have been promoted to manager signals you are liked. Before you make a decision about what to do or not to do, it might be wise to list instances of what it is that makes you uncomfortable and what you would like to ease that. Also more importantly log what makes you feel good about your work –what specific incidents make you feel good–accomplishments, professionalism of those with whom you work, quality of goods and services your work group produces, satisfaction expressed by internal and/or external customers, etc. When we consciously weigh the pros of what specifically happens it increases our graciousness and emotional well-being. These options, some overlap, are best considered and acted on only after being discussed with your boss.

Since you have been employed for some time by a large organization, you might know what rules have been specified or have become customs about boss-bossed relationships or you might check what your handbook or someone in HR can tell you. (Because privacy is vital, I don’t recommend you pose such a query. In most workplaces a close friendship between boss and subordinate is strongly discouraged.)  Possibly, you might get advice from someone outside your workplace.

I invited Lisa Waite, MA, Communication and Professional Development, to add to my comments as a Guest Respondent. I predict you will find her advice below empathetic and workplace savvy.

Kudos to the writer for the emotional intelligence displayed in this circumstance; foremost, understanding the nature of the workplace friendship. However, it is inappropriate for either party (boss & colleague) to be discussing any personal information pertaining to the writer.

I would encourage the writer to ask for change in a respectful conversation.

Something like, “Mary, I am really pleased to work with both you and {name,} however I am uncomfortable when personal details of my life are shared in my absence or otherwise. For example, I learned that you shared details of my recent vacation.

It is simply inappropriate, and I would not do this to either of you. I need to ask that you please not engage in this type of conversation.”

This is effective communication for a few reasons:

  1. The writer states only facts
  2. The writer accurately shares his/her feelings
  3. The message is sent in a manner that allows the colleague to retain dignity
  4. If HR is ever involved, it looks good on paper.
  5. It encompasses the language of leadership. We must advocate for ourselves and role model the behaviors we hope to see in others. I hope this is helpful. –Lisa

Please know that we can’t understand explicitly what has happened and that we trust you will know what is best. We hope some of our thoughts will ring true and/or spur what will work best for you. Working together with hands, head, and heart takes and makes big WEGOS.–William Gorden