update: I hired a friend and it’s not going well

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

Remember the letter-writer who had hired a friend and it was going badly? Here’s the update.

It was really clear from Alison’s advice that either Mike had to go or I had to be better with boundaries – possibly both!

I thought long and hard about whether or not I was prepared to lose the friendship, and decided that I was. I took the script that Alison gave me, as well as the advice from the comments and had a really frank conversation about expectations, the position that I was finding myself in, the fact that ultimately as a manager I needed to be able to separate friendship from work for the betterment of the company, and what I needed going forward. I also asked what he needed that I could provide within the scope of being his manager.

I also realized, through reading a few comments in particular, that while Mike was leaning on me emotionally, that was something I was still doing with him even though we now worked together again. And as soon as I realized it, I owned that piece and cut it out. Upon self reflection I realized it was incredibly hypocritical of me to be leaning on him for emotional support while expecting him not to do the same. I developed what I now call the Andrew rule. Out of all of my employees, one named Andrew was the one I had the best and most ideal working relationship with. So my internal rule became “if I wouldn’t talk about this with Andrew, I won’t talk about it with Mike.”

Mike took it a lot better than I thought and we were able to move forward, which solved the leaning on me problem but not the self doubt problem that he had going on. Mike is actually really good at his job, until he gets in his head. And knowing that I am not a counselor and keeping the Andrew rule in mind, I thought of ways I could, within my managerial scope, assist. What I ultimately ended up doing is when junior staff needed help with the two things Mike was stellar at, I sent them to Mike. I started to establish him as the expert in our team on those things, knowing full well I could trust the results, and his confidence picked up over time. Along with the rise in confidence came the rise in work quality.

I think he also ended up going to receive some help in a mental health capacity after I reminded him of our EAP, but I don’t know for sure (which is the way it should be!)

So I had the conversation and owned my part of it, we have stopped hanging out outside of work (and that will continue until we don’t work together anymore), I’ve developed and stuck to the ‘Andrew rule’, adjusted my own behaviour after realizing how I was contributing to the issue, and I started sending junior staff to him for things I know he excels at. We’re at a good place now and I anticipate it being maintained going forward.

Is it perfect? No, but we’re 95% of the way there, and I am confident that my dedication to being a manager first and foremost, and being okay with the friendship going on hold (or even ending) is what got me through. I also found both Alison’s script and the comments extremely helpful.

Now, would I ever hire a friend again? Nope. Absolutely not. However, given the current circumstances I think we’ve made it work as best we can. It doesn’t consume either of us anymore and work comes first, two things that I am extremely grateful for.

{ 67 comments… read them below }

    1. CmdrShepard4ever*

      OP can you give some more insight into your Andrew rule? I’m pretty sure I understand the broader points of things not to talk about like personal relationship drama etc, but I am asking more about borderline issues if any that came up?

      1. Original Letter Writer*

        Absolutely. A good example is talking about your weekend. Sometimes you have a rough go with family or it maybe wasn’t the best.

        With Andrew, he’d be like “How was your weekend?” And I’d say “Good actually” and name a fun thing I did. Or “Fine, how about yours?”

        With Mike, previously the instinct may be to elaborate on what I did – fighting with a partner or having family drama. Basically anything that came up with Mike, I asked myself “Would I say that to Andrew” before answering.

        Hopefully that helps!

  1. CaliCali*

    I feel like this is a great example of how boundaries can truly help everyone involved in a sticky situation. Good update!

  2. DANGER: Gumption Ahead*

    Such a great update and I am happy for you and Mike. And big kudos for the self-reflection and the brilliant way to build Mike’s confidence while still helping the team. And I love the Andrew rule

    1. RC Rascal*

      I love the Andrew rule as well. This is a take away for anyone who has a problem with professional boundaries, or is a situation where there is a lack of professional boundary.

    2. AppleStan*

      I’m honestly going to take this to heart…this is great information on how to help build someone’s confidence who is having issues. Also, The Andrew Rule (TAR) is now going to be my thing…while I think I’ve done a great job keeping the friendships and the work separate since I’ve been promoted, it was definitely a (slow) work in progress, and I need to ensure that I keep it up. TAR sounds perfect!

      1. Original Letter Writer*

        Thanks to all of you! The Andrew Rule (TAR – I love the short form) has helped immensely even with other coworkers! Sometimes our instincts to relate to others (esp. in a small office or to have discussions with coworkers we are closer with than others) are so strong, TAR helps me not say things I may regret later (instead I’ll text a girlfriend).

        It’s been so helpful and I’m glad it will help you!

  3. Spidey Cents & Sensibility*

    I once recommended a friend who was “so desperate! Will do anything!” for a job. Fast forward to the SECOND DAY(!) she was just sitting there and I asked if she was out of work? She: Yes. Me: Go ahead and ask for something to do. She: No. That is NOT MY JOB. Me: …
    Me to Boss: Fire her if you need to, she is not working out. Result: Fired! I will never refer a friend again.

      1. Johnny Tarr*

        It makes sense to me. A person on day two at work essentially refused to ever go to their manager and say, “Finished that assignment! What next?” I could see the business deciding to cut their losses and not bother training such a weirdly out-of-touch and uncooperative employee.

  4. Not Australian*

    Great update, OP; sounds like you’ve learned something valuable about negotiating tricky situations and managed to retain a useful member of staff, which is so often *not* the way these things work out. Congratulations on finding a viable solution.

    1. Original Letter Writer*

      Thank you! I learned a lot – and actually handling things head on (while still sending me into an anxious mess for a bit before actually doing it) makes a lot of sense. It also really helped me to look inward and see where I may be the problem! I appreciate all the kind comments.

    1. Original Letter Writer*

      Thank you! I have done my best with this situation and believe it has worked out as best it can for all involved. Still never hiring a friend again, though.

    1. CmdrShepard4ever*

      Having to fire a friend can get very tricky. My SO once hired a friend of theirs in what was supposed to be a short term gig. The friend was out of work and job hunting my SO needed a warm body to fill a seat. The friend worked well enough in the beginning and expressed interest in making the position more permanent ( I think the friend got complacent and enjoyed not having to job search.)

      But after a while I don’t think the friend’s performance started going downhill. My SO had a few conversations about it not working out, before making the decision to fire them. They had been prepared to lose the friendship, but the friendship ultimately survived. The friend knew they were doing a bad job and that they didn’t actually enjoy the job. Being fired served as the kick in the pants that they needed to find a better job that they enjoyed.

      I also once worked for one of my good friends when they opened a small retail business. That worked out well for about a year 1 1/2 or 2 until I had to move out of the area. While we still hung out outside of work, I do think our friendship suffered a little bit because neither of us wanted to spend as much time together outside of work as we used to when we had already spent so much time together at work. When we were at work we would socialize a bit, but I knew when he told me to do something it was a direct order from my boss and not a friend.

    2. Original Letter Writer*

      Me too. I do miss the friendship part of our relationship, but we won’t work together forever and things are much more manageable in the office this way. Boundaries for the win!

  5. Marthooh*

    I fully expected the update to be “Mike had to go, alas!” and I’m glad to be proved wrong. It’s heartening that you recognized your own behavior was a big part of the problem. Finding an appropriate way to prop Mike up at work while pointing him at EAP and keeping your fingers out of his mental health is the way management should be done. Thank you!

    1. Original Letter Writer*

      Thank YOU for your comment and for the kind words. It’s nice to have the affirmation that my approach was a good one.

  6. Artemesia*

    I love the idea of the ‘Andrew rule’. Genius way of giving yourself a boundary; glad it worked for Mike too and I wouldn’t hire a friend either. Good lesson.

  7. Mobuy*

    Wait…you wrote in for advice, got advice, took it, and it worked? This is the weirdest update I’ve ever read.


    1. Heidi*

      The best plot twist was where everyone managed their problems in a mature and honest way and took care of their mental health.

  8. Data Analyst*

    Wow, great job LW! I love seeing all updates, but especially ones where someone actually took Alison’s advice rather than deciding they still couldn’t speak up or just getting a new job (both of which I totally understand, but just…it’s nice to see someone win at having the hard conversation and setting healthy boundaries).

    1. Original Letter Writer*

      The hard conversations still give me massive anxiety but they get (slightly) easier with each go. There is no point with carrying on and not addressing things, makes it more difficult for everyone. I’ll take 30 minutes of awkward conversation over months of terrible things any day. Thank you for the comment :)

  9. Detective Amy Santiago*

    This is such a wonderful update!

    The simple answer to so many of the letters we see here is “communicate directly”, but Alison is wonderful at providing scripts for those tough conversations and it’s so nice to see things work out well.

    1. Original Letter Writer*

      I feel like the simple answer to a lot of life is communicate directly! Its such a tough thing to do, because we have feelings – but its so worth it.

  10. Mary*

    >> and I started sending junior staff to him for things I know he excels at

    Both The Andrew Rule and this are just *chef’s kiss* Well done LW!

    1. Sara without an H*

      Yes, excellent management, as well as good self-knowledge and self-management. Congratulations, LW!

    2. Original Letter Writer*

      I love that you used *chef’s kiss* in a comment. I do that all the time. Thank you so much for the affirming words!

  11. your favorite person*

    My husband was hired by the same company as his friend. He got promoted over him and is now his friend’s boss. I definitely just sent him this letter.

    Really excellent work, OP. You did the hard thing and it worked out!

    1. Original Letter Writer*

      Thank you! And good luck to your husband, thankfully that isn’t one I’ve dealt with yet. I have gone from being peers with people to their boss and that’s tricky enough as is! Thank you also for the kind words – its honestly so helpful hearing from everyone.

  12. Ann Onny Muss*

    My former job was an object lesson as to why friends should not manage friends. I wish those managers had their own Andrew rule instead of the pettiness and favoritism that came with the blurred boundaries of friends vs. manager/employee. OP, I’m glad you were able to establish boundaries both for you and Mike.

    1. Original Letter Writer*

      I am also so very glad. It took a while but we’ve made it to what I think is the best we can be.

  13. Janet, Sower of Chaos*

    This is such a wonderful (and boundary-friendly!) way to build his confidence! I’m so touched. :)

    1. Original Letter Writer*

      Thank you Janet – thats really kind. I really appreciate the feedback and lovely comment.

    1. EEOC Counselor*

      It was developed by the OP for her own use. There is no additional information other than what is in this post. But I am going to steal it!

      1. Original Letter Writer*

        It’s a rare day I am called wise *prints out comment and posts it on bulletin board*

    2. BadWolf*

      No outside link — directly from the OP.

      I developed what I now call the Andrew rule. Out of all of my employees, one named Andrew was the one I had the best and most ideal working relationship with. So my internal rule became “if I wouldn’t talk about this with Andrew, I won’t talk about it with Mike.”

    3. Original Letter Writer*


      The Andrew rule was all mine! Think of a co-worker that you have a very appropriate relationship with, boundaried and healthy. Then just put their name in the rule. Every interaction you have with everyone, should fall into the category of an interaction you would have with that healthy, boundaried coworker!

    1. Original Letter Writer*

      Thank you! It has been life-saving in more than just this situation. Fun fact, Andrew doesn’t even work with us anymore (moved on amicably) but the rule lives on in my brain.

  14. BadWolf*

    What I ultimately ended up doing is when junior staff needed help with the two things Mike was stellar at, I sent them to Mike. I started to establish him as the expert in our team on those things, knowing full well I could trust the results, and his confidence picked up over time. Along with the rise in confidence came the rise in work quality.

    Awesome, OP!!

Comments are closed.