If the uncomfortable task of coaching someone on how they dress for work falls to you, you may be struggling with what to say and how to say it in a way that maintains a good working relationship.

Words can be your enemy or your friend in a conversation that strikes so close to the heart of the person you’re talking to.  How we dress is a direct expression of how we feel about ourselves, so asking someone to change can bring up unforeseen issues.  For that reason, using a technique called “FeedForward” is extremely helpful because it removes the sting borne out of criticizing past behaviors.

Here’s how you might tie conversations about appearance to work ambitions and be specific about what you’re recommending.  Use language like, “As you’re well aware, we’re all judged based on appearance – whether or not we look the part.  From past conversations, I know you want to take on a bigger role.  Everyone knows you have the talent to do the job, so that’s not a concern.  One suggestion I have, that will help you look the part, is to start wearing tops that come a little higher up at the neckline to cover your cleavage or skirts and dresses that come to the knee.”   Or, for a man, “May I suggest that you make sure your shirts and slacks are pressed and crisp looking.  In our conservative organization, this change will help you to look the part, which we all know goes a long way toward convincing others that you’re a good fit for the role and will represent the company well.”

If you’re giving feedback to a person who is already in the role and you’re trying to help them refine their appearance, try using statements like:  “I know you want to move ahead.  You might increase your chances if you made a few changes in the way you dress.   Here, those who get the kind of opportunities you want demonstrate their competence, as you already do, and they also dress more conservatively and very professionally.” More examples of specific recommendations might include, “If you’re serious about your career progression, I suggest you begin wearing clothing that is less form fitting, skirts and dresses with longer hem lengths, professionally laundered shirts, wear a shorter hair cut (for men), wear blouses that fit a bit more loosely, or suits that are well tailored.”

Once you’ve offered your suggestions, check-in and listen:  Ask, “Given what I’ve just said, do you have any questions or concerns?”  If the person says, “Nothing; I understand.”  The meeting is over.  If he or she says, “I don’t know why you’re picking on me.”  Respond with, “I’m sorry to hear I came off that way.  That’s the exact opposite of what I intended.“   Or, “This is probably a lot to take in at once.  What if you take a day or two and think about it.  Then, if you’d like to discuss it more, we can.  Could that work for you?” Whichever statement you choose to make, do so, then stop talking and listen.

If he says, he doesn’t agree with you, don’t debate the point.  Simply say something like, “Okay.  I understand.  I wanted to provide this perspective because I thought it might be helpful.  That was my goal.  I regret that I missed the mark.”  Then, let it go.   As circumstances change for the person – new roles, new challenges, new failures – you may decide to approach the topic again, perhaps differently, if that feels appropriate and is likely to serve the person’s best interest.  For now, politely, end the meeting.

No matter what the recipient’s response – “This is exactly what I needed to hear” or “You’re nuts.” – close off the conversation with, “Thanks for hearing me out.  I appreciate your willingness to at least consider the perspective I’ve offered.”

Remember, like feedback, FeedForward is a gift you give.  As is true with all gifts, the recipient can open it, love it and use it immediately, save it to unwrap later, ignore it or trash it.  It’s entirely up to them.  You’ve done your part when you muster up the courage to share the information.