telling someone she needs to look more professional

by Alison Green on March 10, 2009

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.”

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{ 16 comments }

{ 16 comments… read them below }

  1. Allison O'Neill*

    If money is a problem, it may stress her out if she thinks she needs to go out and buy lots new flash threads. Maybe work could provide a voucher? Also I know some workplaces send staff to style workshops, one on one personal style consultations etc. You do have to be very careful how you word anything you say! The “someone told me” when u were starting out is good, as long as sounds very sincere – maybe tell a story of what you used to be like?

  2. A Girl Named Me*

    My first job was in a telemarketing call center — no one cared how I dressed. My second job was in an office building in a downtown location (the year was 1985) and everyone cared how we dressed. There was a dress code — including skirts or dresses for women with pantyhose/nylons as an additional requirement. (Ties required for men.)

    Most companies should have a dress code spelled out in the employee handbook — this way, there is very little room for interpretation and that means less room for hurt feelings. It also addresses the situation as a performance issue rather than as a personal opinion issue.

    My company dress code is something like, “no clothing with holes, no shorts, no bare feet, and no t-shirts with slogan.”

    We’re pretty casual . . . thank goodness.

  3. Anonymous*

    It might be just as difficult to swallow but you could always nominate her for TLC’s “What Not to Wear”. I’ve seen several nominated from work friends/supervisors.

  4. jaded hr rep*

    Professional presentation isn’t always a dress code issue. It’s about not paying attention to the little details of how they look, so they come in with crumpled shirts or the hair is disheveled.

    For me professional presentation is not about designer suits or makeup, but just putting time and effort into making sure the details are taken care of (no missing buttons, stained pants, etc.) and I try to keep my feedback limited to those areas as well. To me the messsage should be: let the client/interviewer know you’ve made an effort to look your best because the meeting is important.

  5. class-factotum*

    This should be an easy conversation. Honestly.

    “Jane. It’s important to our business that you project a certain polished, professional image. You’re a hard worker with a lot of potential. Let’s make your outside match your inside. Here are some ideas: [Show photos from magazines] No sleeveless blouses. Skirts no higher than two inches above the knee. These are good colors for you. Fit, fit, fit. [Stacey and Clinton are so right about this.] A jacket adds a nice finishing touch.

    This doesn’t have to cost a lot of money. I have found some great consignment shops: [list them] Maybe we could go check some out at lunch one day.

    Then let’s go get our hair and nails done at the beauty college!”

    Honestly. I was so clueless when I was 21. I wish someone had done this for me. I didn’t even know how to iron a blouse properly. A co-worker gently asked how I was getting the wrinkles out — which I obviously wasn’t — and suggested I spray the blouse with starch before I ironed it. I did not take offense. Instead, I was grateful because I didn’t look like I had just rolled out of bed and picked a blouse up off the floor.

  7. Kelly O*

    I think we all have to learn that lesson on some level – when I think about the things I wore in the office my first year working at age 20/21 it’s a wonder they didn’t nominate me for WNTW. (I still struggle with what to wear anywhere a good number of times a week.)

    And I agree, makeup is not absolutely necessary, but if you’re going to skip that, it’s even more important to have a good skincare routine, make sure your brows are groomed, etc.

    Like your friend says, this could backfire in a huge way. But, if Jane is really intent on making it in the company and wanting to put her best foot forward, and if the advice is given in a positive and sympathetic way, it might just be the boost she needs.

  8. Rebecca*

    Jane may have NO idea HOW to look good. She might not know how to use makeup. She might not have any clue what clothes look good on her or how to shop for clothes. She might not know where to start with styling her hair. Putting on makeup, dressing well, and fixing hair are all skills that have to be learned, if you think about it. And if you’re not used to putting forth the effort to look good, being thrown headlong into Fashion and Style is going to feel totally foreign and strange.

    I really don’t think there’s any way for Kate to bring this up without Jane feeling at least a little angry or humiliated. Kate has just got to be prepared for that, and also prepared to do or say something actually useful — at the very least, suggesting several books (by different people, lest Jane give up entirely because she doesn’t like the first book’s style). It would also be good to reassure Jane that she’s a valuable member of the team and that the matter is about professionalism and the image the company projects to clients and visitors, not about her as a person.

    Take it from someone who’s been on the receiving end of this kind of conversation. (That ended in a stalemate. I was both angry and embarrassed, informed the boss that I could only afford to shop sales and clearance racks and thrift stores and consignments as it was, and her only advice was… do it at more expensive stores. I didn’t change a thing and never heard about it again.)

  9. Darren*

    I think these kids today (and I say that as someone who’s not that old) just don’t know how to dress professionally. I interviewed a college student for a summer position yesterday who came dressed in sleep pants and slippers. Seriously. I didn’t know whether to say something about it or not.

  10. Anonymous*

    Rebecca- you are so right. These are skills that need to be learned and so many people don’t have a natural talent in that direction so a general comment is no use.

    If this skill is important to the company, and in this position it is, then it’s a training issue so approach it as such.

    ‘You show a lot of promise and the company expects that you will move up. One skill you need to develop is …’ and on you go.

    Lois Gory

  11. Kimberley*

    It isn’t mentioned if Jane is following dress code or not, or even if the company has a dress code. If they do and she’s not, the conversation should be a lot easier “Jane, you remember when you started how we outlined the company dress policy…”

    The company I work for offers image seminars for our clients. Our clients have found it a lot easier to bring in a professional for a lunch ‘n’ learn session on acceptable business attire – rather than singling out one person.

    It’s been my experience that although there may be one person who really stands out in an office, there are usually several others who are also walking the line between business professional and casual dress.

  12. Rosezilla*

    I work in an office where the boss will go with us at lunch to sample sales and go do makeup. I tend to slack and wear jeans and t-shirts a lot, but I love to get in the spirit of getting dressed up for clients/events. When our new intern started, I would tease her about looking midwestern, but I’d also praise her up and down when she integrated some new piece of clothing. It’s hard in this situation, because it’s much easier if you start out in one direction, but I’d make the alternate suggestion to keep it light-hearted and not directed at her. Compare new outfits around her, talk about new salons, hair products, makeup lines. Offer her extra bare minerals or makeup. Get some women from the office to go shopping or to one of those Sheckys Beauty events. Just have the attitude that ‘I’m not going to embarrass you, but I’m going to fix you up, girl!’

      1. Jamie*

        I love that Alison is rerunning the older posts, but we should remember that some of these comments are really old. This one was was written 3+ years ago.

        Just something to keep in mind – the original commenter may not be here any more.

        And fwiw I think we should consider midwestern a compliment – I know that’s how I always hear it, regardless of how it’s intended. :)

  13. Anonymous*

    I think it is important to distinguish the Hurt you may cause by talking to her about appearance Vs the Harm she will experience to her career if you don’t. And it doesn’t have to be too hurtful – you may want to phrase it as “taking your career to the next level – preparing for bigger things.” You may even want to talk to her about other tasks she can perform (stretch assignments?) to help her get ready for the next step. That way the focus is on career development, not merely looks. Letting her know about the unwritten rules of the company is one of the things a mentor does, right?

    As someone who grew up in a rural area, I really needed a clue on how to dress for an urban corporation. Forutunately, a bunch of us geeky girl engineers signed up for an adult education class on how to dress. We had our body types evaluated to learn what styles looked best, we had our colors done, we learned how to “do” accessories, etc. I still use the information 20 years later! You might want to look around for something like that. There are also books in the library that give methods for maximizing outfits using a basic wardrobe. I think the WNTW book also has a listing of such items. If you do this as a group activity it could be quite fun and help her establish a network of work friends.

    The blunt truth is that appearance does matter in business, and if you aren’t wearing the team uniform you’ll be stuck on the sidelines instead of out on the playing field.

  14. JadeMarie*

    My mother used to make my clothes until I was old enough to make my own. You can make professional clothing to the quality of $1,000 suits for less, if you wish. Maybe she should focus on the style issue, maybe find some more professional patterns for her and her mother to experiment with. I made my formals, church dresses, even business suits. If I wanted new clothing, all I had to do was make it. You'd be surprised how often someone asks where you bought something you made because people just don't seem to make things anymore.

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