New Hire Is Dressing Inappropriately? Ask Madeleine

Dear Madeleine,

I am a VP of international sales in technology. We are a fast-paced and very lean startup, so we barely have any HR department and no employee manual yet—certainly no one who can help me with this.

I recently hired a young woman who is just great. She is smart, quick, she goes the extra mile, and she’s crushing her numbers and making friends in the organization. She is quickly becoming my secret weapon. But she has no idea how to dress.

Her taste in work clothing is wildly inappropriate. She dressed perfectly for the interview phase, but now the heels are sky high, the skirts are too short and tight, and the necklines are way too low. People’s eyes literally go wide when she walks by.

I am no fuddy-duddy. I don’t care how she dresses on her personal time. I just don’t want people to get the wrong idea about her. She is so smart and talented and I want to keep her from hurting herself professionally. But I feel the need to reel her in before clients start judging us for her lack of judgment.

What can I say and how can I say it without hurting her feelings or having her think I am somehow judging her or harassing her? I know people in the company have begun to talk about her. I need to do something about this fast.

Victoria’s Secret Not Welcome Here!


Dear Victoria’s Secret Not Welcome Here,

Well, there is some good news: she dressed appropriately for the interview, so you know she has some sense about what is suitable. You have that going for you.

You absolutely must give her feedback and make a clear request. Be clear, direct, and nonjudgmental, make a direct request, and give her a timeline for compliance. Let her know you think her work is terrific and this is not a reflection on her overall professionalism. If you have enough of a relationship, you might go so far as to note that you are partially motivated by your desire to see her succeed and grow as a professional and that you don’t want her choice of clothing to undermine others’ perceptions of her credibility and competence.

You have to have someone else with you in the meeting—preferably someone from HR, even if they are in benefits. If you really don’t have anyone, try to find a trustworthy female peer. This conversation needs to be private, but not hidden.

Your new star may very well have only one or two appropriate outfits and may be trying to get by with her regular wardrobe. Clothes are expensive, and it is time consuming to shop. You may consider offering her a wardrobe allowance so that she can get herself up to snuff quickly.

She may also be trying to express herself and build a brand, which is a thing these days. In this case you can acknowledge her strong sense of style, but say that you need to ask her to channel it. It is hard to get it right for women, but there are excellent sources for guidelines.

If you Google images of “professional attire for young women” you will find lots of helpful photos. You can suggest she find a couple of looks that suit her and build from there. You might also suggest a role model in your organization—a woman who dresses appropriately—if there is one.

Timeless rules of thumb exist for women who want to look impeccable at work. When I was first starting to work in the corporate environment, I had almost no professional clothes and I got feedback from my boss. “Your blouse has to have sleeves; your skirt needs to be no higher than 2 inches above the knee and your heels no higher than 2 inches.” I still remember it because it was so specific, and I have used it ever since. My boss was kind and nonjudgmental. I was embarrassed but I was grateful because I just didn’t know.

She may get defensive and that’s okay—just let her vent. Don’t get caught up in any drama. But you must be clear, direct, and neutral. Remind her that you are on her side and want nothing but success for her. Decide exactly what you are going to say in advance—and do not fall into the trap of discussing it. You will only get yourself into trouble. Tell her you are only going to give her this feedback once and you aren’t going to be the wardrobe police because you didn’t sign up for that job—but you expect to see some changes.

I expect this will do the trick. I sure hope so.

Love, Madeleine

About the author

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response here next week!

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