coworker with a crush keeps hanging out at my desk, exhausted from being the only employee with any drive, and more

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

1. Coworker who (probably) has a crush keeps hanging out at my desk

I was hoping I could get your advice on dealing with a coworker who won’t leave me alone (“Greg”) and is making me increasingly uncomfortable. I’m a woman in my 20s and Greg is a decade older than me. He asked me out a few months ago and I rejected him, and he hasn’t asked me out since. We are under the same organization and our work overlaps somewhat.

Greg works in another building and frequently comes over to mine. While he says he has meetings in my building, he will often come to my desk and sit next to me to chat. He starts awkward, banal conversations (for example, how an energy drink I once casually recommended makes him sweat a lot) and absolutely cannot take a hint that I am busy or not interested. It also feels like he’s watching me (he will immediately look over when my eyes move in his general direction). I feel trapped when this happens, and it’s impacting my productivity when I go into the office. I enjoy chatting with my other coworkers but only when we’re on the same wavelength.

I know I need to be more direct with Greg, but I don’t know what to say. I suspect he is infatuated with me, but I fear telling him I’m not romantically interested will make him defensive and not fix the root of the problem. What are some things I can say to get him to leave me alone without souring things too much?

It’s fine to start with hints because often they’ll work — but once you see that they’re not, that’s a sign that you need to say it more directly. In this case, that means:
– “I can’t talk, I’m really busy.”
– “I can’t have you hang out here, I need to focus.”
– “I’m swamped, can’t chat.”

Also, since you said he’s sitting next to you, is he using a chair you can temporarily move to make it harder for him to plop himself down? If not, it doesn’t really matter because you can still clearly say the sentences above, but if there is a way to make it physically harder for him to linger, it might be worth doing that too.

I don’t think you need to tell him you’re not romantically interested — you presumably made that clear when you turned down a date — but if a week or two of consistently saying the things above doesn’t stop the drop-by’s, you might need to say, “This feels awkward to say but I’m uncomfortable with you dropping by to chat so often after asking me out, and I’d prefer you stop.” My guess is that you’re going to feel rude saying that (since you haven’t felt comfortable telling him directly that you can’t talk to him), but it’s not rude; at that point it’s the clearest way to deliver the message, and it would be warranted. (In fact, I’d argue it’s kinder to just rip the band-aid off and say it.)

2. How can I improve staff morale in hard times with little flexibility?

I am a director at a state agency managing a staff of about 30. We are currently short-staffed by about 10 positions and in a hiring freeze where I have to write lengthy justifications as to why I need those positions. Needless to say, hiring has been slow to non-existent in a process that already took forever.

Staff morale is not great and any time I announce any change, I am faced with negativity, no matter how I phrase it. I would love to try to increase morale somehow. I already began an Employee of the Month program last year, and I make homemade baked goods out of my own money each month for our staff meetings. But I can’t do anything about pay, time off, flex time, or any of those types of perks since we’re state and union. We also have no budget for employee food/parties/gifts. Do you have any other suggestions?

Employee of the Month programs and baked goods aren’t the place to focus. People are demoralized because the team is short-staffed (and I’m guessing overworked as a result), and neither of those things get close enough to addressing that. In fact, sometimes things like Employee of the Month programs run the risk of making the problems worse, by increasing cynicism/frustration if people feel like you expect them to be distracted by a mildly shiny object when there are massive problems. (That doesn’t mean that you’re to blame for not being able to do anything about those problems — just that you don’t want to seem oblivious to them, or like you’re expecting your team to be oblivious to them.)

That said, you can talk to people and ask if they have ideas for what would help! Explicitly lay out the constraints (you can’t do anything about pay, time off, or flex time) but ask them to think creatively about what would make their jobs better or easier. Who knows, maybe you’ll hear that you pushing back on Department X’s unrealistic deadlines or rude behavior would make a significant improvement to their quality of life or that they’d love to get rid of Excessively Long Weekly Meeting Y, or all sorts of other things that might not be on your radar until you talk with them.

3. I’m exhausted from being the only one with drive in my company

I am working for a family-owned business. The environment is laid-back, and the owners are nice and kind. I work remotely with little to no supervision and am considered a key employee for advising and working closely with the owners.

I have realized that, of the entire company and owners, there are only a handful of people who are competent and internally motivated to grow the business. The owners severely lack business skills and knowledge, despite having run the company for more than a decade. My boss, who is a long-time friend of the family and was hired as a consultant, runs the show. He gives them advice on everything and anything, including trivial and basic tasks like how to tally receipts.

In addition to the lack of knowledge, the owners also lack a sense of curiosity and internal drive. While I spend time after-hours finding ways to better the business and increase efficiency, the owners are unreachable after 5 pm. They are still asking me the same questions they did when I started a few years ago. Some of my tasks require input from them and I have to remind them repeatedly even though they are routine tasks.

The slack culture spreads to employees, as there is little to no supervision. When the owners introduced new processes and accountability as I suggested, employees pushed back and refused to perform the new tasks assigned to them. The owners were then afraid of upsetting employees, so they took on the tasks themselves or hired people to meet the demands. My boss asked me to take on additional executive functions because the others are “unable and won’t be able to make these decisions” (in his words) and I declined.

I am feeling exhausted from the follow-ups, having people come to me asking the same questions and fixing the same mistakes. I witness subpar performance from both employees and owners alike. I constantly feel like I am pushing a boulder uphill with a couple of people sitting on it.

The business is slowly facing consequences with reduced profits this year. I did not get my annual raise. My bonus was also lower. I am not learning new things from the job. But I have been able to exert influence and push new initiatives. I am also highly regarded for my contributions to the company. However, I am deeply dissatisfied by the lack of progress and complacency in the organization. My friends and family said that I expect too much from people. How should I navigate this situation?

It sounds like you should find a different job and quit this one! The working environment is frustrating and demoralizing, you have a radically different vision for how things should run than how they’re actually going to run, you’re seeing financial consequences coming down the pike, and it’s already affecting your pay. You don’t need to stay! You can decide to leave and do something else.

If you think over your options and decide that staying there, with all its flaws, is still better than leaving, then you’ve just got to do it with your eyes open: the owners are who they are, their limitations are exactly what you’ve seen, and most/all of what you think should change isn’t going to, but you’re choosing to stay anyway because ____. You’ve got to fill in that blank on your own, but getting really clear on why you’re staying despite all this, if in fact that’s what you decide, should help.

4. Backing out of a talk I thought was already canceled

Last August, a former boss asked if I would give a volunteer professional development session during a series he arranged at my former workplace. Even though I don’t particularly like some of the people who still work there, I agreed, and we settled on a topic where I have expertise and that would be interesting to the audience for a date in May. This March, my former boss let me know he’d been unexpectedly fired, and asked if I’d keep him in mind if I heard of jobs he’d be a good fit for. Of course I said yes, and I mentally removed the session from my calendar.

Now, the day before the originally-scheduled event, I got a text from an unknown number to confirm my session and ask if I need anything for set-up. I let them know that unfortunately, I’d be unable to make it. No one had contacted me until the day before, and they fired the person responsible for the arrangements in the first place; I didn’t realize this was still on and hadn’t done any work to prepare for it, nor would I have known who to contact to confirm.

Certainly this won’t reflect poorly on my former boss, and I shouldn’t feel bad about backing out of something that I was never officially confirmed, right?

Well … I can see how you got there in your thinking, but I wouldn’t have assumed it was off without first trying to confirm that. It was arranged by your former boss, yes, but it clearly got put on some kind of team-wide calendar and someone else took over the planning for it.

That said, it’s not a big deal. It won’t reflect badly on your old boss (he’s gone! he couldn’t have done anything about it), and it probably won’t reflect badly on you either; they’ll just figure it was a miscommunication, which it was. (And really, they should have contacted you sooner than the day before to confirm and to let you know who your new point of contact would be. What if you had needed to cancel two weeks ago? You wouldn’t have known who to contact.)

5. My company wants me to talk to an outside recruiter for an internal position

My company has hired a recruiter for a role that I am also throwing my hat in the ring for. I was told that the recruiter would talk to me, too. But is there a financial incentive for the recruiter to bring someone in from the outside? Just wondering if this means the deck is stacked against me from the outset.

Yes, there is a built-in financial incentive for the recruiter to bring in an outside candidate, assuming they have a traditional recruiter relationship with your company where they only get paid if a candidate they find gets hired. In fact, if this is a traditional recruiter set-up, it doesn’t make sense for the recruiter to talk to you at all! Typically they’d find candidates and present them to your company, and your company would decide who they’re going to interview and assess people from there.

Unless the recruiter is also part of the hiring decision itself (which would be unusual but not impossible), your company should just interview you the same way they’re interviewing other candidates, unless there’s some specific reason they want her evaluation of you (like if she specializes in X, the job is X, and no one internal has the expertise to assess X) or unless they’re not taking you seriously as a candidate.

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