A friend and reader writes:
My friend, who we'll call Kate, is having a problem with one of her staffers, let's call her Jane. Jane is a staff assistant and a hard worker who wants to stay in the office and move up the ladder.
Kate likes Jane, but some people in the office don't take Jane seriously. Part of this is that she's not assertive enough, which Kate has talked to her about. The other part is her appearance. [Insert disclaimer about how appearance shouldn't matter here], but this is an office where people are judgmental and you need to cater to that to get ahead. Jane is the first person you see when you enter this office, and her clothes don't fit quite right (her mother makes them for her), she doesn't wear make up, and her hair is kind of a mess. Jane is young, and Kate has told her she should try to figure out how to look older and more professional, but that didn't really work.
Kate really likes Jane and wants her to move ahead, but she's not sure how to get these points across. Her concern with coming out and saying "You need better clothes, to wear makeup, and get a new haircut" is that Jane will get offended. Do you have any advice on what she should do?
How comfortable is Kate with candid, potentially awkward conversations?
Telling Jane to try to look more professional hasn't worked, so Kate is going to need to get more explicit about what that means.
Ideally, Kate would talk to Jane somewhere private -- maybe take her out for coffee or something -- and say, "Hey, I think this professional look thing is something you're struggling with, and I don't know if you realize it's something that will affect how you're perceived. And I think you have tons of potential and so I want to help."
One way to minimize the awkwardness is to explain that it's not uncommon for recent grads to struggle with this. I'm a big fan of just saying, "Someone had this conversation with me when I was starting out and it was really helpful, so I'm going to have it with you." The vibe should be "you're not a freak for needing someone to help you with this."
Then, rather than saying that Jane looks messy, it's probably more tactful to present it in terms of needing to come across as more polished. And she should definitely explain what she means by that, because it's quite possible that Jane has no idea. Saying something like, "In this office, it really helps to pick clothes that are more tailored and wear your hair in a more polished way" is more useful than just "you look unkempt."
If Jane replies that she can't get different clothes on her salary, Kate should be prepared to suggest low-cost options. You can get business suits in thrift stores, after all.
(By the way, I would probably leave makeup out of it, since I think there are plenty of professional-looking women who don't care for lipstick.)
So ultimately, my advice is really these two points: Be specific about what you mean, and do it in a way where Jane can feel normal.
What do others think?
UPDATE: A different friend just sent me this, which I think is a good point: "I think she could bring it up, be direct, etc. like you said, but when I've had this conversation, all with people who respect me and look for me to give them advice, they haven't listened and were hurt/offended.
I kind of think that this is the sort of thing the person has to want to hear. I think she needs to know why she wears the clothes -- because she likes them? Because she likes that her mom makes them? Because she doesn't have the money? Because she doesn't care about how she looks? Because she's still in the college mindset? I think the answer to that really directs what the person should do next."