Ask the Admin: My Boss Is Having An Affair

By | Sep 1, 2010

We have a doozy of a question this week, folks, and I’m hoping some of you can help the writer with some advice:

I just found out that my boss is having an affair.  Normally I wouldn’t care.  I mean, who he sleeps with is none of my business, isn’t it?  The part I’m having trouble with is that I like his wife.  A lot!  She’s in and out of the office all the time and she attends company events with him.  She’s such a sweetheart, and I feel just terrible about all of this.  I hate to see her taken advantage of.  So what do I do?  Do I tell her about the affair?  Or do I protect my boss?

Andrea (not my real name)

Andrea, thank you for writing to me about this problem.  You certainly have a serious dilemma on your hands.  Situations like this can cause you some serious heartache.

Confidentiality: How far does it reach?

I’ve always been a big advocate of keeping your boss’s personal business confidential.  An Administrative or Executive Assistant is so much in her boss’s pocket, that she tends to learn many things that she might otherwise not want to know.  If we are to maintain the level of support to our boss’s that they need, they need to be able to trust that anything we learn is kept strictly confidential.

My question would be how you learned about the affair?  Was it through your work duties?  I know that I’ve come across the same knowledge in the past looking for an e-mail my boss couldn’t find.

My gut says if you found out about the affair in the performance of your work duties, then you owe your boss your confidentiality.  However, if you found this out in a non-work venue, then you are not so bound.  For instance, if you heard about it from someone in your social group.

Assuming you didn’t find out from work duties, I’m still of two minds about telling the wife.  You still have to worry about your own position and the possibility of retaliation from your boss.  It could make your job very, very difficult.  It’s a matter you have to wrestle out with your own conscience.


I know Andrea and I aren’t the only two who have made this discovery.  I see the topic in search often enough to know it isn’t an unusual happening.  I’d love to hear from all of you, my readers, on this topic.  How far does confidentiality reach?  Would you tell the wife in these circumstances?  Please, leave a comment and tell us what you think.

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14 Comments so far
  1. Wendy Peek (1 comments) September 1, 2010 12:26 am

    I think the Andrea should keep this information to herself because she is the only one that is going to be hurt either way she chooses. If she said something to the wife then the boss will retaliate or if she says something to the boss the wife may retaliate once she does find out about the affair and confronts Andrea about not telling her. I don’t envy the situation you are in but if I were you, I’d keep my mouth shut.

  2. Jonas (1 comments) September 1, 2010 3:47 am

    what ever happen, you should never betray your personal values.

    Just because you are at work – this doesn´t mean you are a neutrally person.

    If you have a problem with cheating, you shouldn´t bite your tongue and feel uncomfortable all the time.

    Maybe you should give your Boss the chance to tell it to his wife first.

    But the reason why he is cheating is probably because nobody ever told him there is something wrong with it.

  3. Wendy (2 comments) September 1, 2010 7:05 am

    Wow, I’m so glad I’ve never faced that decision!

    My first instinct is one of caution. If you’re looking to stay at the firm, I don’t see how it could possibly work out in any way that’s good for you. I’m assuming the boss doesn’t know that you’ve made this discovery either so have the opportunity to keep on with business as usual for you two. I think you would be best served to keep your find to yourself until you are out the door.

    Even then, you have to accept that references from this guy won’t be good either. In other words, you’ll have to be prepared to write off your time with this firm almost entirely even after you’ve gone.

  4. Mary B (3 comments) September 1, 2010 9:55 am

    I also am very glad I’ve never been in this situation. But here is what I think I would do. If I had the knowledge from a work source, as Jodith said above, then I believe I would have to keep it confidential. However, if I found out socially, unrelated to work (someone I knew outside of work told me they saw them, etc.), I think I would have to let my boss know that it was “out there”. The person who told me might tell someone else and it could get back to his wife. In this way, you let him know that you are trying to protect him (as a good assistant would do), and let him know that there is a chance his wife may find, but not from you. This way, you assure him of your confidentiality, and gain his trust. You have to protect yourself, especially in this economy, and if you tell the wife, your boss could make it hard for you to find another job as an assistant (harsh truth – even if illegal!).

  5. Cleo (1 comments) September 2, 2010 10:30 am

    I stumbled across this Blog today, and I first want to say thank you to Jodith for a wonderful place to ask questions, get answers and fantastic information. Well done!

    I was reading the question and answers above and was quite stunned, for I do not see this as a challenge, but an opportunity. I think every Assistant takes pride in her work – serving her boss. But what does serving mean – Do I do it only at my convenience and in my best interest (like keeping my position in the workplace safe?) Or, do I really care about my Boss (which includes his family).
    Just ask yourself this question “What would YOU like someone to do when they found out that your spouse is cheating on YOU?”

    I might be very contradictory but I do believe at the end of every career, financial fortune and success in life, we all remain humans with a heart…one that can be broken. I believe in respect, I believe in trust, I believe in honesty and I believe in keeping the family unit together and healthy. I don’t think the issue really is “How far does confidentiality reach”, but rather, “what is my true motive when it comes to confidentiality?” Is it to serve myself and my best interest, or is it to serve my Boss and his best interest (which includes his family).

    I’m not suggesting that you spill the beans irresponsibly, but that you look at the heart of the matter, (which extends beyond your job and your confidentiality to your boss), and handle this in a very caring and tactful way.

    How? Write your boss an anonymous note informing him that you are aware of the situation and that suggest he discuss it with his wife otherwise you will inform her. Give him an “x” amount of time to handle the situation and if he doesn’t, you write his wife an anonymous letter and inform her about the situation.
    What will be your motive for doing this? Simply to give your boss a second chance (just like we all need one), to perhaps restore his beautiful relationship with his family. For me, this is how we are truly assistants to those above, around and below us – to not just care about our pay checks and “job security”, but about the people that makes up our daily life and gives us the chance to make a difference in someone’s life.

    I hope I didn’t come forward too strong, but instead, that you will realise what an amazing opportunity you have to save a lot of people, a lot of pain.


  6. Jodith (189 comments) September 2, 2010 11:15 am

    Wow…thank you all for all of your thoughtful comments on this issue. Andrea is indeed in a tough situation here. I appreciate all the input you gave her. I like Mary’s idea of talking directly to your boss about it. That was the tack that I took when I made my discovery, but my boss and I had a really good relationship where I felt comfortable discussing it with him and letting him know that if I found out what I did, someone else certainly would, too.

    I also like Cleo’s idea, because it is a way to protect yourself while still addressing the issue.

    On one level I’m loath to be the one to break such news to someone’s spouse. I know from my parent’s marriage just how devastating infidelity can be in a marriage. By the same token, though, how do you fix problems in a marriage if you don’t know they exist?

    This is a hard topic, and I thank all of you for commenting giving Andrea so much to think about. Andrea, if you feel up to it, let us know what you eventually do. I know all of us here could benefit from your insights as well.

  7. Joseph (1 comments) September 12, 2010 5:38 am

    Spread the word about this affair through an anonymous email Ask yourself this question.. If your husband was having an affair. Would your friend that knew about it be a friend if they never told you? One more thing, You don’t owe your boss any confidentiality or anything else. This is not a business issue and even if it was, it truly doesn’t matter. People are more important than workplace politics.

  8. Kitty (1 comments) September 13, 2010 1:33 pm

    I think you should pretend like you don’t know your boss is having an affair. It’s not really business and you should just forget all about it. First of all you do not want to jeapordize your career over your bosses sex life. Second you state that the problem you are having is that you like his wife. If you really like her don’t put her though the pain and the misery of finding out that her husband is cheating on her. I think it would be selfish of you to tell his wife about his affair. It might make you feel better, but it in no way does anything to make her life better. If I were you I’d pretend I knew nothing about it and get to work.
    Kitty´s last blog post ..Have An Affair At The Office

  9. zero down traffic blueprint (1 comments) September 14, 2010 3:21 am

    I don’t see how it could possibly work out in any way that’s good for you. I’m assuming the boss doesn’t know that you’ve made this discovery either so have the opportunity to keep on with business as usual for you two.

  10. Vic (2 comments) November 24, 2010 9:21 am

    Andrea should not say anything. It is Andrea’s place as an assistant to keep all of her bosses business, work or personal completely private. I think Andrea should remember that first and foremost this is and will become a work ‘issue’. You work for him, you know his wife through work, and if is gets out it could not only ruin his personal life but also his work life and Andrea runs the risk of it also ruining her personal life too. I think people who take it upon themselves to inform others of such things are actually border line stirrers. Whether the boss is having an afair or not is no one elses busines – including Andrea’s, but seeing as Andrea knows, it is still her obligation to keep it to herself. Afterall, she came across this snippet of info accidentally, she was not told about it! I have been in this situation twice in my career. It doesn’t make you feel proud of the person you look after, and once I even confronted him about it – in retrospect he was pleased I did and it turns out the whole situation was a lot more ‘messy’ from all angles – and not so cut and dry as I had assumed on my discovery of the email. That taught me not to be so judgemental too.

    But ultimately it’s not your job to get involved in his marriage crisis – it’s your job to work for him in a confidential capacity. So, really, you shouldn’t tell anyone.

  11. joe joe (1 comments) December 7, 2010 2:39 pm

    unless you have concrete proof, if you accuse him he will deny it. You will be fired and he could even sue you. not a pretty sight.

  12. Lauren (1 comments) December 30, 2010 10:31 am

    I worked for a man who was having an affair with someone in our office. He was the owner of the company; I was his assistant….I was also friends with his wife who I really liked.

    One morning when we came in to work we found that all of the women’s desks had been gone through. Apparently his wife was suspicious and came in and tried to find clues. Sad to say I know he was having affairs with at least 2 of the women in our office.

    Shortly after we arrived she phoned him. About 15 minutes later she phoned me and asked if he had told the person he was having the affair to leave. This was so difficult. I didn’t want to lie to her so I said not yet. Then she spoke to her husband again.

    Next my boss called me into his office and told me if his wife called and asked if the woman was still there I was to say no. I told him I didn’t feel comfortable lying to his wife and would prefer not to be in the middle of a personal situation. He basically told me if I didn’t comply I could lose my job. I think it was wrong of him to bring his employees into the situation. He should have left and gone home to work it out with his wife.

    In the end he had someone else pick up his phone who didn’t mind lying to his wife. About 4 months later I was let go from my position with 3 months severence. The good news is I had been looking for another job and I received a call one day after I had been let go and was at a new job a week later. That was lucky for me.

    Honestly, as much as I liked his wife I would not have said anything to her because that issue was between he and his wife. But asking me to lie to her – I felt that he had stepped over the line.

    I felt truly blessed that I had never lied to his wife and had found a new job so quickly. Basically you have to make the choice as to what is more important to you, However, most of us need our jobs, and it is sad that we are at times put in these types of positions.

    Additionally, He was one of 4 men I worked for in my career who were having affairs. He was the only one who wanted me to get involved in lying to his wife. Unfortunately this goes on more than we would care to think and we must learn to be professional and handle it discreetly.

  13. Cooter1954 (1 comments) August 20, 2012 4:37 am

    I am in this situation and I did tell the wife. I know her well and knew she wouldn’t betray me by telling her husband where the information came from. I would not have done it had I thought she would tell him, but I know sooner or later my values would get the best of me and I wouldn’t care.

    Right now she has plans to have him tailed on his next “business trip” where we know he will be with the other woman. It’s going to crash down on his head really quick here, and she will wind up with more than half his money (tens of millions). Good for her!

    Just in case, I am currently planning on moving to another state and get another job. I’m near retirement age so whatever happens will have no effect on my livelihood.

  14. Jennifer (2 comments) February 18, 2013 11:45 am

    I wanted to chime in on this if it’s okay. I think that you have to consider all sides of this before you act. First is about your job, although you may have a great job, do you really want to work for a man that would cheat on his wife? If not, I would start looking for another job and then, after you have moved on, find someway to tell his wife. On the other hand, if you have no qualms about working for such a man or don’t think you have a choice (i.e. you can’t find another job), then you have to go with your morals. You could always just keep quite, but from your letter, I don’t think that is what you want to do. So another suggestion would be to tell his wife anonymously. Just slip a printed card (don’t write it out incase someone recognizes your handwritting) in the mail to her that says “Dear Mrs. XX, although I am unable to reveal who I am in person, I fell that I have a moral obligation to tell you that your husband is having an affair. Please forgive me for not being able to give you more details, all I can say is that , if I were in your shoes I would want someone to tell me.”

    Goodluck “Andrea”
    Jennifer´s last blog post status update

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