My Junior Employee Sends Rude Emails

And two other tricky workplace dilemmas.

EXPERT OPINION BY ALISON GREEN, INC.COM COLUMNIST @ASKAMANAGER

JAN 8, 2025

Photo: Getty Images

Inc.com columnist Alison Green answers questions about workplace and management issues–everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

Here’s a roundup of answers to three questions from readers.

1. My junior employee sends me rude emails

A junior employee I manage writes rude emails. He will send three emails in 15 minutes, and then respond rudely when I answer the first one, as I haven’t gotten around to the other two or hadn’t seen them in my inbox yet. He’ll respond quoting his previous emails I haven’t had time to look at yet. Or if I respond, he will ignore the answer and resend it, again quoting himself. Every email is condescending and liable to ramble.

I asked another person to look at our email conversations, and they agreed that they’re rude. I also was warned before I started that he was a difficult person to work with.

Should I talk to him about this? If so, what’s the best way to explain that some of his email habits could be considered rude? (If they even are. Maybe I’m too picky?)

Green responds:

It doesn’t sound like you’re being too picky. What you’ve described is rude, or at the very least annoying. Someone else reviewed the emails and also agreed; I don’t think you need to second-guess yourself!

But rather than getting into a whole explanation of why he’s coming across rudely, why not just tell him, clearly and matter-of-factly, what you’d like him to do differently? For example, you could say, “Please save up your questions for a single email rather than sending multiple emails in quick succession. Or, if you can’t avoid that, please wait for me to to finish responding to each email rather that repeating your questions after I’ve only had a chance to respond to one of them.” When he ignores an answer, you could respond, “I answered this previously; please see the email I sent you this morning.”

You manage him, so you have authority here. Use it by calmly and directly telling him what you want to see him doing differently.

2. My boss is mentoring my employee

In my work as a director, I’m recognized for being highly inclusive and engaged in the success of each person on my team. I regularly meet with my employees and coach them in real time.

With that said, one of my employees has set up a mentor relationship with my boss. When my employee first talked to me about setting this up, I thought it seemed like a great opportunity for her. But then I started to question whether it was odd for my boss to mentor one of my employees.

Today, my boss spoke to me about the arrangement and said that I should expect to see major changes in my employee professionally and personally now that she was being personally mentored by my boss.

I have encouraged my employee to find a mentor in the past and advised her that often the best mentor is outside of your immediate organization. I think I’m questioning whether or not my boss agreeing to the arrangement is a good idea. Am I being close-minded? Do I need more education on mentoring?

Green responds:

No, it’s a little weird. Certainly a boss (or boss’s boss) can be an informal mentor — I’ve mentored some of the people who have worked for me, and most good bosses do the same. But the nature of the relationship limits the ways a manager can truly act in that capacity, especially formally.

You share things with a mentor that it might not make sense to share with a boss, at least not as candidly — things like areas where you’re struggling, frustrations you’re having, thoughts about moving on, etc. You might share some of that with a boss, but the boundaries are a lot more narrow than with a mentor; with a boss, you need to consider how the info might factor into her thinking in ways you don’t want or intend. And there are some topics about which a boss won’t be the right sounding board, such as if the mentee wants to talk about when it’s time for her to move on or whether the organization is a healthy one to stay in (since a manager may be swayed by her own interests, even just unconsciously).

In your case, where the boss/mentor is two levels up, your employee may want to ask for advice about working with you in ways that can be very tricky for both you and your boss to navigate. It could also lead to her circumventing your authority in ways that normally wouldn’t happen.

Now, maybe your boss doesn’t mean “formal mentor.” Maybe she means she’s investing in your employee’s development because she’s talented and the two of them have good rapport. That’s fine! But without a better understanding of exactly what she means, I can see why the framing makes you uneasy.

3. How do I express concern without prying?

I’m a manager of an employee who’s had to take a lot of time off for doctor’s appointments. This is not someone who would take advantage of time off, so that’s not my concern, and is someone I have a relatively close relationship with. What’s the best way to express concern or support for their well-being without seeming too intrusive or sounding like I want to know more?

Green responds:

“I don’t want to pry, but I hope everything is OK, and please let me know if there’s anything you need from me!”

They can then either offer more if they want to, or can ignore it and move on.

That said, there are times when I wouldn’t recommend saying even this. If you’re a manager who does tend to pry or who has expressed skepticism about someone’s sick days in the past, this can come across as fishing for info or signaling you’re watching their time off. But in a healthy environment, it will be fine.

Want to submit a question of your own? Send it to alison@askamanager.org.

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

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