Dear Prudence

Dear Prudence Uncensored: The Startup Dress Code

Every week, Danny Ortberg and Nicole Cliffe discuss a Prudie letter. This week: the startup dress code.

Nicole: I do not think this person has much of a problem.

It’s super annoying when companies are like “no dress code!” and you then get in trouble for wearing business casual.

You mean “we want to look like a startup”

Danny: There is often a reason that companies have formal dress codes that are written down!

Nicole: Just wait until your next meeting w your reports and say this is the deal. They can wear jeans! It’s not a big ask.

Danny: Obviously formal dress codes can bring problems of their own, but.

Nicole: Yes, absolutely. If they want to eye roll, they can.

Danny: and make it clear that commenting on your clothes is not on too, yeah?

Nicole: RIGHT, absolutely

Danny: that’s certainly within your purview as their manager

Nicole: This is where you work now, guys. Sorry about Enron or whatever.

Danny: lmao

Nicole: here we dress like we play ultimate frisbee

Danny: this is definitely the business equivalent of that age-old romantic problem of wanting your significant other to read your mind

Nicole: AMEN

Danny: “We want everyone to dress casually! A very specific kind of casual! But we’re not going to outline that anywhere, because that would not be casual.”

to be clear i don’t blame the letter writer for this attitude! This sounds like a company problem, and I think the LW is new to management and has possibly not been given much in the way of training or backup

Nicole: Absolutely. This is also a marker of companies that have “evolved” past adequate HR staffing. Just grit your teeth and deliver the news.

Danny: how do you recommend delivering it? just like, “this is coming from my boss, it’s a specific command”? or holding to your own authority and saying “I’ve requested this in the past but i want to make it clear that you need to wear Office Beer Garden Casual”?

Nicole: “We’ve talked about this before, but dressing more formally than is appropriate for this workplace is still a problem. Is there any reason that change will be difficult for you to make?”

Danny: Oh God, I would crumble at that question IMMEDIATELY, like shortbread or the city of Jericho.

Nicole: Just remember that being clear and firm about your expectations is a gift. It’s the woolly wussy bosses who cause real problems for their staff.

Danny: yeah and if the perception that your employees are standoffish continues then you’ll need to address that

Nicole: Yes! It’s a real problem. I am ITCHING to manage these people.

Danny: but the matter to discern there will be - do they refuse to cooperate or withhold information? or are they just not joining in with the quietly mandatory company “vibe”?

You would be a beautiful and terrifying dark queen of a manager.

Nicole: Right! Your soul is known only to God. BUT YOUR OUTPUT IS MINE.