AITA for speaking to my (over weight) assistant about her business lunch and making her cry?

At the beginning of the year, I hired an assistant (we’ll call her Amy). Amy is great at what she does and I have already given her a raise because I felt she was underpaid for what she was doing. I’m working on several large deals, so I gave Amy the lead on one of them.  She did an excellent job. 

I set up a lunch appointment with that client on Friday.  I told him I would be bringing Amy as she has been instrumental in their account.  He did not have a problem with this.  Amy was professional, knowledgeable and did an overall good job.  The client and I were both impressed, with the exception of one thing.  The client and I both ordered burgers and fries.  Amy ordered a steak- well done- mashed potatoes, steamed veggies and a side of soup.  The client and I finished about the same time. It was another 15 minutes before Amy finished.  Then the waitress came around and asked if we wanted dessert.  The client and I both said no.  Amy ordered cheese cake and coffee. 

I realized that I hadn’t spoken to Amy about client lunches before, so after the meeting.  I explained to her that it is best to follow the client’s lead.  If they order simple food, we order simple food.  If they decline desert, we decline desert.  If we want something afterwards, we can pick it up later.   

Amy did not take this well.  At first, she offered to pay me back.  I told her it was not a money issue.  I have no problem buying her lunch but to keep in mind it’s about business.  I told her I usually order wraps or burgers because they are not too messy (like spaghetti) and I can take small bites in case I’m asked a question.  I can also match the client’s eating speed so there is no awkward waiting on either side. 

Then she started crying, saying it is because she’s fat (her words not mine).  I again told her it was about strategy.  I thought she had great potential and I wanted to help guide her.  I then told her about some of my past faux pas.  For example, ordering spaghetti and getting it all on my shirt, or once I ordered first and ordered a cheese burger when the client was vegetarian and highly disgusted at me.  

She was still upset when she left.  I feel like an AH for bringing this to her attention but my intentions were good.  I feel like she has great potential.  The meal did not concern me as much as how she took instruction.  Now I’m wondering if others think I was wrong for bringing it up at all.  

14 thoughts on “AITA for speaking to my (over weight) assistant about her business lunch and making her cry?”
  1. NTA, it’s business etiquette not far shaming.

    She’s probably sensitive on this so there might be no safe way to have the convo, but your approach is right

  2. >Amy did not take this well. At first, she offered to pay me back. I told her it was not a money issue.  

    There is no way you can get someone who is determined to misunderstand you, to understand you. You did not comment on her weight and her theatrics speak to her and whatever she’s dealing with internally. Professionally, this is a huge red flag for Amy. 

    I know it is hard to hear especially given the crying and all that, but you are NTA.

    1. What’s the saying? “You cannot reason a person out of a position they did not reason themselves into”

    2. This feels like the type of behavior of person who can’t accept they did anything wrong and instead turns the attack around on the other person.

      I understand this is one incident, but it’s something to watch out for. I’ve had co-workers and past partners like this. Once you notice it, it reappears everywhere.

  3. NTA

    I am also an overweight person. I would never ever think of ordering steak if I worked in a client facing job and the client didn’t order something fancy first! It wouldn’t even occur to me to do so.

    I do understand that she may be feeling very sensitive about her weight, a lot of us fat people do, but not every conversation about food is an indictment. If she wants to be in your field, she needs to know the strategy.

    I also get why it didn’t occur to you to have the food strategy meeting ahead of time, but I hope that if this happens again with someone else that you will do so.

      1. That. I always come at it from a perspective of treating the client. The client gets to have an extra perk or side. I get a similar or smaller item so I can focus on the substance of the discussion and their experience interacting with the team.

  4. NTA – Business lunches are weird. So many unwritten rules and pitfalls. As her boss, you offered advice and examples of mistakes made in the past. As her boss, it’s literally your job to mentor and guide her in these situations.

    Also, dessert has two S’s. 🙂

  5. NAH.

    But next time you are taking someone out for lunch I’d explain the expectations BEFORE the meal.

    1. I disagree. I am not in the business world but I would know not to order a steak when others are ordering something simpler and not to order desert when the client passes. This should be simple etiquette.

      1. It should be common sense, but it’s not for some people.

        I certainly am not going out to eat on someone else’s dime and ordering food way more expensive than what the person who is picking up the bill ordered.

  6. NTA. As a plus size woman, I do not see a problem with this advice at all. She sounds insecure and needs to understand it is about the timing out of respect for the client, not the food itself.

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