Dear JT and Dale: My boss and his family attend the same church as me. One day after Sunday Mass, I heard from other parishioners talking about him and some of the health issues he was experiencing. I know my company knows nothing about these health issues, and they are quite serious – they could impact their decision-making and could harm the business and our livelihoods. Do you think I should send an anonymous note to HR regarding the situation? I would hate for something to happen and then they find out I know. —Cassie
JT: I’ll take a look at your employee handbook. There might be something specific in there that requires you to share that kind of information. If so, then I might see you go ahead and send a note to HR anonymously. However, if there is nothing, then you should say nothing. His health is his business, and he has clearly used his church community as a safe space to share what he is facing. If he wanted the job to know, he would have told them. It is really his responsibility. So, for now, I would be as supportive as I can be of the workplace, but I wouldn’t say a word.
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Dear JT and Dale: I have started a side hustle in the pandemic which is doing very well. A good friend of mine keeps telling me she wants to help me. I’m pretty overwhelmed and could use some extra help, and she’s enthusiastic, but I’m afraid that if something goes wrong with me as boss, it could ruin our friendship. What do you advise? — Noah
VALLEY: I think it is wise to have doubts. I’ve had wonderful experiences working with partners, but no luck with friends as employees. There is a role disconnect that gets in the way and it hurts both relationships. Moreover, it hurts in surprising ways: as Oscar Wilde once wrote: “Anyone can sympathize with the sufferings of a friend, but it takes a very fine nature to sympathize with the success of a friend. The point here is this: your friend will want to know more and be more than an employee, especially in good times, and that will be a pebble in someone’s moccasin.
JT: Working with someone you’re good friends with can be an absolutely amazing experience, as long as the boundaries are clear. I think you have to ask yourself first: how strong are your communication skills as friends? Have the two of you worked through difficult conversations together? Are you able to be honest with each other and not let things escalate or grow to the point of exploding? Because if you’ve done it in your current relationship, it’s probably going to be easier for you to do it in your professional relationship. Also, I think you need to set clear ground rules about how to approach things with each other and when to know when to quit.
Jeanine “JT” Tanner O’Donnell is a career coach and founder of the leading career site www.workitdaily.com. Dale Dauten is the founder of The Innovators’ Lab and the author of an HR novel, “The Weary Optimist”. Please visit them at jtanddale.com, where you can email questions, or write to them c/o King Features Syndicate, 628 Virginia Dr., Orlando, FL 32803.