I can’t get answers about a special project, candidate with risqué photos online, and more

It’s five answers to five questions. Here we go…

1. Internship offered me a special project but now I can’t get any answers about it

I’m a college student who recently finished a remote internship at a prominent company in a fairly niche field (the company has maybe 10-15 full-time employees). My main task was fairly generic — think setting up a filing system or similar — but I also got a lot of experience in the actual field. Towards the latter end of it, I had a great talk with the CEO about what I wanted out of the internship, and what was really exciting was that he said that he thought a good next step for me would be designing an accessory for one of their products. That sounded great to me, and I said so. He told me to get back to him with some ideas for products that I wanted to make an accessory to, and that he would meet in a week or two with some of the designers to talk about what they thought and hash out the plan for this.

That was about one and a half months ago. I sent some messages after that attempting to follow up. Initially he just hadn’t gotten around to the meeting yet, which was fine, and said I should send him what product I was interested in working on, but then he didn’t respond to that. Once my internship wrapped up I sent a message thanking him for the internship, and saying that I would be more busy but still available during the school year and would love to work on other projects with the company. He replied saying it was great to have me there for the summer, but also that he was not sure what would be next with regards to project work as they are still figuring out what things will look like in 2026. I sent one more message a week and a half later, saying that I’d love to talk more about the accessory design project and once again affirming that I am free despite being in school, which I haven’t gotten a response to.

I have been in intermittent contact for other reasons with one of the designers who was my boss during the internship, and a few weeks ago I asked if the CEO had gotten a chance to talk to him and the other designer about the design opportunity, or if plans had changed. He said he would remind the CEO about it … and I haven’t heard anything about it since.

Should I send yet another message to the CEO asking about this? I don’t want to come off as pushy or badgering, considering I’ve already sent him at least four messages about it, but this would also a really exciting opportunity for me. I think it’s very possible that plans changed or he realized that he wouldn’t be able to actually offer me this opportunity, at least not right now, which I would understand. But in that case, I would just like to at least hear that, rather than continue getting radio silence.

It’s probably not happening right now, for whatever reason. You shouldn’t continue to message the CEO since four messages makes your interest really clear and the ball is now pretty firmly in his court. The one thing you could do, though, is to message your boss from the internship again and say something like, “I’m not going to keep bothering Cecil about this since I haven’t heard back and I’m guessing it’s just not something he can move forward with right now, but if you do think there’s anything else I should do on my end, please let me know! I’d love the opportunity if it might still be possible, but I realize it might not be.” But after that, I’d assume they’re just not able to make it come together right now.

2. Should we not hire candidates with wet t-shirt contest photos online?

I’m hiring for the restaurant and bar at a golf course, and we recently have had two openings for servers. We’ve had trouble finding suitable candidates until recently, when two university students who are both friends applied and interviewed back to back. They are literally the perfect candidates who we believe have the skills to help our team.

Upon checking their online history, however, we found out that last year they were overseas at a hostel and they joined a wet t-shirt contest. The hostel and nightclub posted some images on their website, with them both showing off their butts in thongs and also removing their shirts entirely, showing their breasts to the crowd. They actually finished first and second in the contest, and kudos to them! Personally, I don’t have an issue with this and I see it as good fun. I don’t see how this would impact the reputation of our golf course in any way, as the customers will not know and, even if they did, it’s not like they would view this as something the golf course was then up too. I really don’t think it matters. Neither does the other hiring manager, but they are hesitant because they “just know if you find something like that, you are not supposed to hire them.”

Do you think we should just hire these wonderful women who seem to be the right fit for our job openings or do you think the fact that their butts and boobs happen to be on a hostel website from overseas matter and we should pass? I personally think in today’s times that this sort of thing is okay and I think the other manager is living 20 years ago still.

You should hire them. Tell the other manager that the advice she’s heard is outdated and it only ever applied to certain types of jobs anyway (like jobs like teaching, where public image has traditionally been a big concern). It never applied to the majority of jobs, and it has zero bearing on their ability to do the work you need done.

3. Can I ask to use a “free” day off at a different time?

I work full-time in local government, in a small office of 12. Recently, our boss sent out an email announcing that as a thank-you for our hard work over the past year, she was giving us all one “free” day of personal vacation. We were all told to look at the calendar to see which day we were assigned to take off.

While I appreciate the thought, I was actually hoping I could bank the day off and use it towards a vacation later in the month I was already approved to take. Alternately, I wanted to ask to use my “free” vacation date on my birthday, also later this month.

Would you advise asking our boss if I could use the free day she is giving us towards another vacation or on another day? I don’t want to seem ungrateful or look at gift horse in the mouth, but the day I am assigned to be off is not a day I want to be off. She has never done anything like this before, at least since I have worked with her. She’s normally pretty tough about granting time off requests, so her willingness to randomly give us an extra free day took me by surprise.

Sure, ask! “Would it be okay for me to use this for January 30 instead? That’s my birthday and I’d love to use this to take it off.”

Or you could ask to use it for your already-scheduled vacation, but there’s more chance she’ll feel like you’re turning what was meant to be a feel-good perk into something more administrative since you already have that time scheduled — which doesn’t make logical sense, since it would mean you had an additional day to use down the road, but I suspect the birthday would be more in keeping with the spirit of what she’s trying to offer.

4. Should my exempt employees be using PTO for appointments?

I’m a faculty member at a university, and I supervise some staff members. These staff members are all exempt and have all been in their roles since before I became a supervisor. I’ve noticed that they will use a few hours of annual leave in order to take a pet to the vet or for various other things that might require coming in late or leaving early. They will also sometimes “make up” hours in the evening if they had to come in late or leave early during the week. Their roles are 8 am – 4:30 pm positions that require at least one of them in the office during this time.

From following your site, I was under the impression that, as exempt employees, they don’t need to be taking leave for these incremental hours of time they aren’t working. This all gets a little more complicated, because technically I supervise one person, and she supervises the other two employees. I have deferred to her on how she wants to manage office coverage and their tasks. She’s also been supervising employees for much longer than me, so I deferred to her on how leave is supposed to be used and reported. (Remember, this is a university, so I went from a regular faculty role with incredible flexibility to a supervisory role without being given any real information on how HR-type rules work. Academia!)

Ultimately, my question is whether these employees are unnecessarily using their leave. Should they be able to come in late (if approved) and not use leave? And if so, is this something that I legally need to fix? Would we be in legal trouble if it came to light that exempt employees were being required to use leave in this way?

So, first, the law on exempt employees doesn’t say anything at all about how they need to use their leave; it is exclusively concerned with their pay. Specifically, exempt employees be paid their full salary for any week in which they do any work (with a few narrow exceptions, like if they’re working a partial week because it’s their first or last week of work). But the law doesn’t care if that money is coming from their paid leave or not; it only cares that they are paid. So there’s no legal issue here.

What does matter are your employer’s personnel policies, and maybe also what’s common practice in your department. Some employers (and some managers) strictly require that people use PTO for the sort of thing you describe (or make up the time). Others are much more flexible and figure there’s a give and take, and as long as people’s work is getting done, they’re not going to nickel and dime them on PTO. So the question for you, first and foremost, is what your university’s policy is on this and, if it’s fairly strict, whether you as a manager have standing to choose to implement more flexibility on your team.

5. Can I apply at an organization that’s not hiring?

How do I write a speculative application to an organization that isn’t hiring right now? Is that even something I should try?

I really want to get out of my current job (law enforcement) and have found an NGO that I’m a perfect fit for. Unfortunately they’re not hiring at the moment, but I’d like to send them my resume in case it’s something they’d consider now or in the future.

I’ve never sent a speculative application before. Is it a good idea? How should I structure it? Do I turn the email into a cover letter, or write a separate cover letter and attach it like I would for a listed job ad?

I wouldn’t be considering this if I weren’t certain that I’d be a great asset to the organization, and this level of self-confidence isn’t typical for me. But I don’t want to make a fool of myself and blow my shot in case it hurts my chances in the future. What would you advise?

You definitely can try doing this! There’s no guarantee it will lead to anything, of course, but there’s no reason you can’t give it a shot.

You’d make your email your cover letter, explaining why you’re contacting them and what you could offer them — and why you’re so interested even outside of any specific position being available — and then you’d say, “I’m attaching my resume so you can see my full professional background, and I’d love to talk if you’re ever hiring someone to do X.”

People do this a lot, especially with nonprofits (because they tend to attract a lot of people who want to work for that cause, specifically). It won’t hurt your chances for the future at all (if anything, it could help them).

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