Dear Madeleine,

I am a COO in a multi-national import business. Our founding CFO has a foot out the door and we want to promote our comptroller, Bridget, into the job. She is lightning fast, ahead of the curve on international issues, articulate, and can really stand up for herself in what is—let’s face it—pretty much a man’s world. She has her MBA and she seems to be ambitious.

The problem is, Bridget has no idea how to dress. This may seem superficial, but we are all charcoal-suit- with-the-white-shirt guys. She dresses like she buys her clothes at Victoria’s Secret and she wears way too much makeup. Her unprofessional appearance totally distracts from her good qualities.

So far she has worked behind the scenes so no one has said anything. But if she were promoted we would need her to take part in client meetings—including in Asia and the Middle East—and she would need to look professional and upscale.

No one knows how to approach Bridget about this. We are actually considering just passing her over and starting a search. What do you think?

Buttoned-up Suit

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Dear Buttoned-up,

I think it would be sad for both Bridget and you—not to mention expensive in both time and money—to pass her over and launch a new search before making an attempt to solve this problem. What a waste if you have someone already on staff who is almost perfect.

I have to wonder: where is your HR department in all of this? I can only assume they are also buttoned-up suits and don’t even see this as their problem since you are the one writing. You obviously believe in this woman and want to see her succeed, so I encourage you to make the effort—but you will need to tread lightly.

It would be absurd to overlook someone who knows and gets along well with all of you, who will have zero learning curve about the company, and who is incredibly competent. But I understand the dilemma and I believe Bridget needs to hear the feedback and act on it. This is no small feat, but it can be done. It is not that unusual a situation but there are some big hurdles here—so you have to decide if they are worth the effort.

Have the talk.

It would be ideal if you could find a female executive who could have a talk with Bridget—but it sounds as if that might not be an option. So someone—maybe your HR person, maybe you—is going to have to man up and sit down with your whiz kid. In the conversation, make it crystal clear that her current way of presenting herself may well be holding her back—and that she needs to literally show the executive team that she is willing and able to up her game to be considered for this promotion.

This needs to be handled sensitively, but if it is clear to Bridget that the person giving the feedback really has her best interests at heart, it could work. I am speaking from experience. I went from being an actress to working in the corporate world and had no idea how to dress. My new boss, whom I trusted, gave me feedback after my first client session: my skirt was too short, my heels were too high, and I shouldn’t wear sleeveless blouses. I was truly embarrassed, but I knew it wasn’t personal and I was grateful because I knew my boss had my back. I went shopping and started a collection of what I considered work uniforms.

Be specific.

When talking to Bridget, use neutral language to describe the problem. Be very specific without adding value judgments. An example: “We think you are great at your job—but in order to consider you for any promotion, we need you to dress more professionally. You’ll need to wear blouses that have short or long sleeves and that fit properly, are not revealing and do not gape. Your heels should be no higher than 3 inches, and the length of your skirts and dresses should be no shorter than 2 inches above the knee.” (I would say no higher than fingertips of extended arms, but some people have short arms and anyone over 50 really should not be using that rule anyway.) Emphasize that clothes should fit properly and not be tight.

If you aren’t really sure, consult a website—there are tons. Here is one: What Is Professional Business Attire for Women?

Offer assistance—and understanding.

You might consider offering Bridget a wardrobe budget so that she can quickly and completely rebuild her work wardrobe. This process takes years for most of us. It would help to suggest a personal shopper as well, and equip Bridget with pictures of what you would consider to be appropriate. Also, think about gifting her with a lesson from a professional makeup artist to help her find a daytime appropriate work look.

Dress and presentation are rooted in culture and deeply personal. Many people see how they dress as a fundamental form of self expression. You can have conversation about this. Women who dress provocatively in the workplace are often following a role model that makes sense to them; or they really enjoy making an impact; or they simply believe it is what is expected of them. I have worked with many employees over the years who see the way they dress as a political statement and feel, therefore, that clients should be okay with it. But nothing will ever make it okay for an outside consultant to wear Birkenstocks to a meeting at Goldman Sachs. I often compare dressing for success to wearing a costume to make the right impact on a specific audience.

Present rationale—and time line for the shift.

Make it very clear that this is not personal—it’s because you believe she will be more effective if she is able to match the way she presents herself to the culture of the organization. Certainly remind her that in her personal life she can, of course, wear whatever makes her happiest.

Set a reasonable target date for when you expect to see a substantial change in how she presents herself. Expect that you will need to give her a few second chances—and when she shows up at work wearing something unsuitable, gently but specifically point out to her what is inappropriate.

Be realistic about the outcome.

Finally, keep in mind that she may not be able to make the shift. I have seen it happen a couple of times. This would also be sad but at least you will have made the effort, and she will have been given the  opportunity. Some people will never compromise their self image for any reason.

This is a tricky situation. It touches on gender equality issues, personal identity, and the compromises we all make to fit into our tribes of choice. But it is not as if you are a nasty boys’ club asking her to wear tighter, shorter skirts. That would be a real problem. You want to invite her to be in your executive level club—where you know she deserves to be. But to get that invitation, she needs a costume change.

Let me know how it goes—and good luck!

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.

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