Young office slacker cause of consternation for small business

I run a small real estate development firm with only three employees. I research and bring in the deals. My partner manages the dayto-day operations, and we have one general administrative assistant. At the same time, we work with and have relationships with everyone involved, including general contractors, architects, designers, realtors and subcontractors. At any given time, there are a lot of balls in the air, and attention to detail is critical, which brings me to my issue.

One of our biggest investors has a nephew, and because he wants his nephew to get some experience, he asked whether his nephew could work as an intern for us. I talked to the kid, and he seemed nice enough, so we hired him for the summer. Since then, he’s been a bit of a disaster.

The kid comes in late and leaves early. He is sloppy with his work, horrible on the phones and borderline illiterate through email. He’s the winning combination of entitled and incompetent.

I don’t want to upset the investor, but we’re a small, scrappy firm and this degenerate is sticking out like a sore thumb and creating more work than he is producing. I don’t want to bite the hand that feeds me, but I need to run my business.

— Rock and Hard Place

You’re wise to be cautious. When it comes to family, objectivity tends to go out the window. If you complained to your investor, he might become defensive, even if his nephew has the work ethic of a trustafarian sloth. That said, he did want the boy to get work experience; surely, he can appreciate that constructive feedback is part of that.

So offer the intern some specific pointers. His emails are terrible? Share examples he can model his after. He’s bad on the phone? Spend a few minutes each day role-playing calls. If he doesn’t improve, give him tasks that aren’t customer-facing, such as scanning documents.

In the meantime, work on a diplomatic response to have ready the next time an investor tries to get a relative a job at the firm so you’re not between a rock and a hard place again.

I work at a boutique consulting company with incredibly smart people who have different knowledge bases. The staff is truly diverse, ranging in age from 22 to 72, and everyone gets along, for the most part.

We have a company dress code that says something like “no open-toed shoes, no jeans except on Fridays, collared shirts must be worn,” etc. It’s essentially business casual from 1997.

I’ve noticed a change recently, especially from the younger people. They have no regard for the dress code.

Don’t get me wrong. They all look very puttogether and extremely fashionable. It’s not as if they’re showing up in hoodies and flip-flops. They might wear a hoodie, but it’s a slim-fitting, hip hoodie over a button-down with dark jeans and Chuck Taylors. Straight out of a Levi’s commercial. Part of me wishes I could pull that off — I would love to come into work feeling comfortable — but I don’t want my supervisors to think I don’t care about the rules.

These younger co-workers look OK, but they are technically breaking our dress code, and for some reason, that bothers me. It’s not about the clothes. It’s more about my perception that they’re getting a free pass. Am I being a fogey, or am I onto something?

— Not Anna Wintour

A dress code is part of company culture, but sometimes the culture evolves and the rulebook becomes outdated. Talk to management and ask for clarification. Maybe management will decide to revise the policy to allow more casual attire. Regardless, try worrying less about other people’s jeans.

Send your questions for Annie Lane to dearannie@ creators.com.