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

1. Employees don’t participate in our community outreach activities

I’m a part of the “good will” committee for my office location, as well as the large committee for the whole company. Lately I’ve been feeling a struggle of getting other employees actively involved in our initiatives. Good will is a named tenet of our company, and we have a pretty healthy annual budget to go along with it.

We try and have one or two initiatives per month that have varying degrees of involvement. Sometimes it involved volunteering onsite (during work hours or directly after). Sometimes it’s asking for donations (gently used books or unexpired canned goods/shelf stable foods). We’re not asking people to go and spend their own money on things. The most successful ones are in-office, during office hours, but there’s only so many opportunities for those.

We also try and cover a variety of different areas — unhoused people, kids/schools, food scarcity, women, LGBTQIA+, community gardens and book depositories, animals, BIPOCs groups. We also ask employees about groups they would like to see us support.

I just feel like it’s been a struggle lately to get people involved. People never seem to have issues finding time for sporting events or happy hours, but no one seems to want to do a shift at the food bank. Shocking, I know. Any ideas on how to get people motivated?

They may not want to. Some people want to spend their limited downtime relaxing, and that’s okay. I’’m not sure it’s appropriate for an employer to try to change that.

People are exhausted right now, and they’re at work to earn money, not to volunteer. A lot of people who are charity-minded do their charity work on their own time, and don’t feel their employer needs to claim the credit for those efforts. If your company wants to do good in the community, that should mean it’s coming from your company’s resources — its money and its time (meaning that this should all happen on work time, not after hours, and other work needs to be moved aside to create space for it; the expectation shouldn’t be that people’s regular workloads don’t change at all to make room for it). If the company isn’t willing to do that, then this is just a value they’ve stuck on a list, not a genuine value they hold.

All that said, I think you have the answer when you say, “The most successful ones are in-office, during office hours, but there’s only so many opportunities for those.” If people aren’t interested in ones outside of that category, that’s feedback worth listening to! And if there are only so many opportunities for those, then maybe you stick to those because that’s what employees are up for.

Beyond that, talk to people! Survey employees on what they are and aren’t interested in participating in — both in terms of specific activities and general categories of activities (during work hours, 5-7 pm, drives where you bring items from home, etc.), and also ask how they’d like to see the company live out this value. That’s what ultimately should shape it.

2. Should I tell my manager about a recurring issue with a coworker?

I’m a receptionist at a small healthcare-adjacent company and would appreciate your advice on a recurring issue with a remote customer service representative, “Donna.”

Callers frequently report being hung up on a few minutes after I forward them to the customer service line. Almost every caller who tells me this has mentioned they were speaking with Donna when it happened, which is a problem I don’t encounter with any other representatives.

Because our work involves urgent health-related matters and long wait times, these disconnections can be pretty significant for our clients. Sometimes they’re sitting in the queue listening to hold music for 20 or 30 minutes before having to start over again because upon being transferred to Donna, they get disconnected.

Thing is, I’m hesitant to report this to our supervisor because the guy is a severe micromanager, and I want to avoid subjecting anybody to having to deal with him. I’ve been the subject of his ire before, and it’s not fun when his laser beams get trained on you. However, I’m growing concerned that Donna may be intentionally disconnecting calls, or has an unstable remote connection. How would you suggest I handle this situation?

You need to tell your manager about it. It’s a significant issue, and it’s got to be incredibly frustrating for your callers — and your position means you’re probably the only person (other than Donna) who’s aware of it. Your position does give you standing to raise it, because you’re partly responsible for the experience that callers have when they contact your company. (That doesn’t mean you’re responsible for whatever is happening once you transfer them, of course — just that when you have info about their experience that no one else has, you do need to make someone higher up aware.)

If that mean Donna gets micromanaged … well, some closer management might be needed here, because either Donna is intentionally disconnecting callers or is aware she’s frequently losing her connection and not bothering to ask for help to get that fixed. Or maybe she has, in which case she’ll presumably explain that to her boss — but either way, this is something you should escalate.

The subject line of your email to me was, “Is it appropriate to snitch on my coworker for this?” and this is not snitching. This is letting your manager know about a work issue that’s highly relevant to how well your organization is serving clients.

3. Disabled and losing access to parking

I work at a university that recently announced a major campus construction project that will eliminate a significant amount of central parking, including areas closest to my building. The announcement framed this as an exciting improvement to campus life, but for some of us, it creates a serious accessibility problem.

I have a disability that affects my mobility. Even now, I arrive over an hour early just to secure one of the limited nearby parking spots, and I still face a several-minute walk to my building, which can be difficult depending on the day. I am not the only one who does this in my building. There’s several of us who do this daily. With these lots closing, we are all extremely concerned that we simply won’t be able to access my workplace in a reliable or sustainable way.

This is the second time in a few years that staff parking has been reduced. In this case, the project will also remove several accessible parking spaces across campus, and they are not being replaced.

The university’s suggestion is to contact parking services for alternatives, but based on past experience, those alternatives are not workable for me. They typically recommend using a shuttle system, which is difficult for me to physically navigate, or parking farther away. Factoring in wait times and travel, that could add close to an hour to my commute each day. I also have religious commitments after work on Fridays, and this added time would make it difficult or impossible to attend. The shuttle isn’t always the most reliable. It’s also small and with more people probably needing to use this, it could add in well over an hour to my commute daily.

Another option is purchasing access to parking at a nearby institution, but that requires an upfront cost of over $700 annually, which is not financially feasible for most people.

My job could be performed remotely, but remote work is not currently offered as an option, and I worry that pushing too hard on that could negatively affect my job security.

I have not reached out to parking services, as I am not optimistic about the response they will give. Historically, the university has been resistant to feedback on parking and accessibility concerns or they ignore emails totally. Another colleague reached out to them with these exact concerns, but she’s certain she’ll not receive a response or they will not care as they have when there were issues with parking spots blocked off earlier last year.

At what point does this become an ADA issue? What are my options for advocating for reasonable accommodations in a situation like this? Would requesting remote work on days when I cannot access parking be reasonable, or am I better off pursuing a formal accommodation through HR or another route such as an anonymous ADA complaint?

It’s an ADA issue now. Under the ADA, employers with 15 or more employees are required to provide accessible parking as a reasonable accommodation for workers with disabilities, and they must engage in an interactive process to find solutions if spots are unavailable.

You should submit a request in writing to HR with the subject line, “official request for accommodations under the Americans with Disabilities Act.” Don’t go through parking services since they’ve been unresponsive; approach it as a legally required medical accommodation with HR.

4. Independent contractor vs. employee

I have a question regarding W2 vs 1099 contractor definitions. I understand one key legal difference is a contractor sets their own hours. Does that mean that no employment where I commit to showing up at a certain time can be a 1099? Like, let’s say I am a tutor. I choose my students and can let them go. But let’s say I sign on to tutor someone intensively for you hours once a week for a semester at a specific time slot, and I sign a contract to that effect, do they now have to give me a W2?

The IRS doesn’t use a black and white test for contractors where if you don’t set your own hours, you can’t be a contractor. Rather, they look at the totality of the circumstances. They look at three factors: (1) behavioral — does the company control or have the right to control what the worker does and how the worker does their job? (2) financial — are the business aspects of the job (like how the worker is paid, whether expenses are reimbursed, and who provides tools/supplies) controlled by the company? (3) type of relationship — are there written contracts or employee-type benefits (insurance, vacation pay, etc.) and is the work a key aspect of the business? The law says, “Businesses must weigh all these factors when determining whether a worker is an employee or independent contractor. Some factors may indicate that the worker is an employee, while other factors indicate that the worker is an independent contractor. There is no ‘magic’ or set number of factors that makes the worker an employee or an independent contractor and no one factor stands alone in making this determination. Also, factors which are relevant in one situation may not be relevant in another. The keys are to look at the entire relationship and consider the extent of the right to direct and control the worker.”

There are independent contractors who commit to working set hours. Doing that doesn’t on its own make you an employee.

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

1. Company said I could move after my husband took a new job and now they won’t let me

I work for a large corporation with a Remote First policy, and compensation is location-based with three tiers. While their policy says permanent relocations must be approved, there is no employee-facing material that says relocation is not allowed up a tier. For example, there is nothing saying someone in a lower cost of living city (Tier 3) who needs to move to a high cost of living city (Tier 1) will not be approved.

My husband applied for and got a job in a Tier 1 location. He flew out to start the job (his start date was four days after the offer). I immediately told my managers, and they said they didn’t anticipate an issue so we prepared to move to the new location.

 I’ve been with the company for five years, am a top performer, and have won several awards for performance. My direct managers and the org manager approved the move, but last week I learned that the upper leadership have not, due to a policy of not approving moves up location-based pay tiers. My managers had never even heard of this policy. My husband had already accepted the job, started work, came back to help me pack, and the day before all our items were to be shipped across the country we got this news.

I have appealed the decision and my managers have outlined the business cases for me staying to leadership. But as it stands right now, I have 90 days where I can work from a non-home location but after that I’ll have to quit or be terminated. I asked HR if I could remain at my Tier 3 salary through the next review cycle (as I realize that budgets have been allocated, etc.) but that was denied since remaining at a different salary tier in a new location is not “company policy.”

I’m at my wits’ end. My husband has been out of work since Covid, this is an amazing opportunity, and he has already accepted the job. We can’t live in the new area without both of our salaries. I was definitely not expecting to lose my job because I moved, and I’m terrified of looking for a job in this market.

I’m currently going back home alone to try to buy as much time before my 90 days starts. My husband wants me to get a lawyer, but I don’t know if I have a case or if a lawyer could do anything since I’ve not been fired yet. My job is extremely specialized and I’m very happy in my current position and I just don’t know what to do.

I’m sorry, this is a mess. If your company promotes itself as “remote first” organization, they need to be much clearer with employees about what restrictions they have on that. If you can’t move to a location with a higher pay tier than your current one, it’s ridiculous that they haven’t proactively told people; their lack of transparency is what led to this, and it would have been so easy for them to avoid it.

Are you able to tell your company that you’re going to stay where you are? Whether or not you really do plan to stay there long-term, telling them that would presumably stop the 90-day clock from ticking and buy you and your husband some time to decide what you want to do, which could include living in separate locations until one of you can move to the other, you looking for a job out there, or him coming back (basically returning to the situation from before he got the job, which would be brutal but is an option). But your company sucks for putting you in this position and not being willing to make an exception considering the circumstances, and particularly when you’d been told by multiple managers that it would be fine.

2. How do I lean out of my company’s DEI work?

I’m a boomerang at my current company (meaning I left but have now returned). When I was previously employed here, I ended up leading our women’s ERG, as well as leading or being a critical stakeholder in a variety of DEI-related groups and activities. Ultimately, despite doing this work for several years, and passing the baton to capable passionate folks when I left, many of the key metrics related to increasing diversity at all levels but particularly in management have not changed or have changed for the worse. Ultimately, I have come to believe that the many extra hours of unpaid labor my colleagues and I contributed did little more than create good press for the firm. I think that if the firm is committed to the goals it ostensibly signed on to, then such efforts need to come from the top and include real numeric goals in hiring and promoting, along with resources for professional development, none of which were ever really forthcoming.

Now that I’m returning, I’m more interested in pursuing social justice goals outside the firm with organizations that demonstrate real commitment and effectiveness in their efforts. I know as part of our upcoming goal-setting conversation, I’m going to be encouraged to take up some of my old work and I absolutely won’t. We have volunteer PTO hours available, which I am happy to use for outside-the-office work. How do I thread this needle in conversations with my grandboss, who also happened to be the exec sponsor of the ERG I used to lead? (Honestly, I think my company has no business or claim on this stuff but I need to check a box, so…)

If you’re asked to pick up that work again: “Oh, thanks for offering, but I’m not interested in stepping back into it again.” If you want, you can add, “I’d like to leave it with whoever has been handling it or give someone new a chance to take it on.” If you’re pressed about why, feel free to say, “I’ve realized that work needs to come from the top of a firm and people at lower levels aren’t well positioned to do it.” If pressed anyway: “I feel strongly about it, so I’m going to pass.” If you want you can add, “It’s something I work on a lot outside of work and I don’t want it to become part of my job here as well.”

3. Can I suggest my difficult boss get more emotional support?

I have a question about a boss who I don’t really like, but I also think he’s not a bad person so I don’t want anything bad to happen to him.

I work in a law firm, and this guy is one of the salaried partners. He has bullied a couple of people out of the team, but always been very respectful to me. Even so, because of his behavior to others, I’m not a fan. He has always been a bit unreliable — there is not a single time he has gone on a business trip or holiday when I have been told in advance and had a plan. Every time, he just disappears, and then there are timezone issues that neither I nor the client were prepared for. But, by and large he has kept up with work and I’ve had a decent time learning from him.

Recently, he has dropped the ball SO BADLY. Clients are complaining and he is continuing to disappear without warning, but he’s managing it even worse than he previously did. He is failing to turn up to calls that he’s said he’ll attend. I know he is going through a divorce, although that’s been going on for eight months now, and it’s only recently that he’s gotten really bad.

I hate the way that he is affecting junior staff, and I have been communicating with management accordingly. However, I am also worried about him. I might not like him, but I don’t think he’s a bad person, and I think this really AWOL behavior is pretty worrisome, even taking into account his usual behavior. I think he is a typically manly man who has not considered the resources available for mental health issues. Is there any way I can check in with him, and offer him some judgment free support, without being inappropriate?

You’re not the person best positioned to do that. His partners or other senior members of the firm are. You are positioned to do the piece that you’re already doing (communicating with management about what’s happening). You could certainly suggest to one of them (perhaps that most empathetic-seeming among them) that he might benefit from a nudge toward some support, but beyond that you’re just not well placed to do it. (It’s not that it would always be impossible to suggest that to someone with more power than you, but typically if you had that kind of rapport that would make it natural, you’d already know it.)

4. When employers say “we’ll keep your resume on file,” will they actually look at it again?

Do employers look at past resume submissions when a new job opens, or do they just look through the new submissions? Does “having a resume on file” actually mean anything?

It varies. Some companies say it as part of their boilerplate rejection letters when the chances of them ever contacting you again are low. But other companies do look through past applicants when they have new openings, particularly for hard-to-fill roles and particularly when they need to hire again soon after a similar role just closed. People do get contacted by companies for openings they might be well matched with after previously being rejected. You just can’t really tell from the outside how likely it is. Either way, there’s no point in reading much into it, and if you see an opening there in the future that you’re interested in, proactively apply — don’t assume they’ll contact you.

Related:
does “we’ll keep your resume on file” really mean anything?

5. Can I ask for more pay in lieu of benefits?

When I was looking for my first job out of college, a mentor suggested I negotiate for higher pay since I was under 26 and could still be on my parents’ health insurance. I actually did need health insurance, and in fact it was the primary reason I was looking for a job, so I did not take this advice, but I’ve always had it in the back of my head.

I got married in the past year and am now on my spouse’s (far superior) benefits. I’m wondering if it would be wildly out of touch to try to negotiate a raise in lieu of benefits now, or if that’s something that can only be done when starting a job. (Or is it even something one can reasonably do when starting a job?)

Factors to consider: This is a relatively small company (fewer than 50 people). Our industry is having a tough time, largely due to current administration issues. Raises last year were paltry, though honestly I was surprised to be getting one at all. I’ve never negotiated salary before. Our raises are calculated at one (fairly arbitrary) point in the year, and they’ve always been presented as, “This is what you’re getting this year.” Maybe some people negotiate within that, but I never have felt like that was an option. I’m a high performer and fairly senior, and have been here for more than five years.

You can ask! Some companies will do this and some won’t. Typically if they do, it’s done as a separate line item in your benefits, not just added to your salary (because if your situation changes in the future and you do need to start using their insurance, they don’t want you to feel like you’re getting a pay cut), so you wouldn’t frame it as a raise — just something like, “Would the company consider offering a stipend or credit for not using the company health insurance, since that saves us money?”

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

1. My boss told me my dresses need to be longer

My line manager told me yesterday that there had been “comments made” about how short / inappropriate my dresses are in the office, as a member of the team who is front-facing for clients. I was asked to not wear these outfits in the office any longer.

These comments have utterly humiliated me, and I spent about an hour crying on my way home. I have always dressed fairly modestly at work and am deeply uncomfortable with my body being perceived as being “on display.” My dresses are long-sleeved, with skirts that stop just above my knee. They are conventional office wear. I prefer dresses and skirts over trousers, as the medications I take have made my stomach quite bloated, and I find tight waistbands uncomfortable. But I was told they need to be longer as I’m greeting clients (as my work wear was just above the knee already, my presumption is that longer means to the knee or below).

It’s a very male heavy office, so what other women wear is split between trousers and skirts that are above the knee or to the knee. My line manager was wearing an above-the-knee dress the day after telling me my outfits were too short.

After looking at my work wardrobe, I estimate I’m going to have to get replace nearly 80% to get to these new standards — of dresses and skirts to the knee or lower — while also managing the other restrictions that are placed on women’s wear at our office. For instance, I’m not allowed to wear a sleeveless blouse because our male directors decided they are not professional for women. This is while the men in our office can meet with clients in hoodies or polo shirts.

I simply don’t understand why my clothing is an issue 16 months into working here. Am I being unreasonable or is this unfair? Is this something I should speak to my union about?

Yes, you should absolutely speak to your union. Something here doesn’t make sense — skirts and dresses to just above the knee aren’t unprofessional or inappropriate work wear, and that goes triple in an office where a bunch of other people are wearing them, including the manager who told you that you couldn’t. “You’re client-facing” doesn’t make sense as an explanation. Is there anything else that could explain why you’re getting this feedback and others aren’t? Sometimes this happens when you’re the only one in your office with a particular body shape (which doesn’t make it okay), and I wonder if that’s in play here.

Ideally you’d go back to your manager and ask for clarification — including explicitly asking if she is telling you that your skirts must be below the knee, and pointing out that all your skirts are currently the same length as the ones you see other women in your office wearing. But since you have a union, pull them in for advice too.

2. CEO sends a delusional AI-generated image of himself with every email

As a mere lower-level staffer, I am certain there is nothing I can do about this issue, but perhaps you have some ideas.

The CEO has begun to attach an AI-generated image of himself to every email he sends out. The images are universally more handsome than the real thing. No more receding hairline, or stomach fat. Plenty of bicep muscles. Not a wrinkle in sight.

This is cringe behaviour, and staff mock him for it behind his back. While I am not personally invested in helping him save face, I do want to stop being forced to look at these unprofessional, inaccurate portraits. Especially since the workplace is a public library, where one would hope to avoid misinformation.

No, this is amazing and you must not try to stop it!

And that’s fortunate, because there’s almost certainly nothing you can do about it anyway. If you were, say, a senior communications staffer or his right-hand person or otherwise a trusted confidant, you could attempt to diplomatically address it, but assuming you are none of those things and therefore have no real standing or obligation to take this on, the only correct response is to sit back and bask in the utter absurdity of it.

Is it a problem for his credibility? Yes! Is it your problem? No.

You can just enjoy the spectacle.

3. I wish my board would just fire me already

I am the chief executive of a small nonprofit and I report to a board, and I have been on a performance improvement plan (PIP) for the past four months. The PIP is full of things that are untrue and half true, along with some things that could legitimately be improved. The PIP was my first notice of any of those gripes that the board (or rather, a few members of the executive committee) had about me, my work, and, more pointedly, my personality.

The first PIP was supposed to be 60 days. They had no objective success measure in it and missed over half the weekly check-ins we had scheduled. They are having a lawyer handle everything for them, so I didn’t receive a determination about the PIP until a couple weeks ago when they gave me another PIP with a 60-day extension. This document, even more than the first one, has things in it explaining where I am failing to meet expectations that I was unaware of and were not part of the job previously.

At this point, it is clear that at least two of the board members just don’t like me and want to fire me, which is completely within their power to do. I have sincerely done what I can to meet their expectations, but I can’t and won’t change my personality or pretend to be someone I am not. And this job has turned into something different than what I was hired for.

I have been looking for a new job since the process started, but it is not easy at this level and I can’t afford to be without an income or I would have quit already. How do I have the conversation with them expressing my desire to leave along with my need to be eligible for unemployment benefits?

Frame it this way: “It’s clear to me that you’re unhappy with my work and I want to be realistic about my chances for success here and not drag out the process, so I’d like to propose a managed separation with a transition that will be as smooth as possible for both of us. I’d ask that you not contest my unemployment benefits since it sounds like I was likely to be let go at the end of this process anyway, but beyond that I’m flexible about what this could look like in terms of timing and messaging.” They are likely to hear this with relief.

You might also consider whether you have an argument to request severance, if they’re now defining success in the role differently than what you were brought on to do.

4. Requiring 15+ hours of outside reading per week

I am curious to your take on a job listing I recently came across. There is an indie bookshop in my city that is looking for booksellers — basically part-time retail work, $12/hour starting wage, nothing atypical for the area.

Amongst the qualifications and job duties listed, alongside needing 3+ years experience as a bookseller and “associates or better” degree, I noticed something that seemed super wild. “Booksellers are required to spend an additional 15+ hours a week reading recent releases and bestsellers to stay up to date on merchandise and better assist customers.”

(I am assuming the 15+ hours of reading homework is unpaid, but I could be wrong; this is a very hipster bookshop that I like to visit now and then but would never work at personally, so I haven’t inquired further or anything.)

Is this as bonkers as it sounds to me? Or does this sound more like “continuing education” and is pretty reasonable to expect?

As a general rule, if outside reading is required for non-exempt employees, they need to be paid for that time. There are exceptions for things like continuing education required to maintain a license, but booksellers aren’t licensed.

They’d be better off saying that they’re looking for employees who already maintain a deep knowledge of recent releases and bestsellers and who will maintain that knowledge going forward — and then screening for dedicated readers of recent releases (which is different from just being a voracious reader in general) in their interview process — instead of presenting it like a job duty with a specific number of hours attached.

5. I was fired from my last job, then didn’t work for several years — how do I explain it in interviews?

I was fired from my job several years ago. Due to a combination of burnout and undiagnosed depression, I effectively went AWOL and didn’t do anything about anything until it was too late, and I’m trying to re-enter the job market now. I have a resume gap of several years, my previous job loss was entirely my fault, and it’s been a very long time since I had to do any kind of job searching.

How do I write a resume to cover this particular ground? And, in the event of an interview, any advice on how to answer the inevitable question of what I was doing while unemployed? (The honest answer is “nothing, while trying to claw my way out of a mental health hole.”)

You don’t address it on a resume at all; that’s the place to highlight your work history and accomplishments. In an interview, the language you want is: “I’ve been dealing with a health issue that is now resolved and I’m excited to return to work.” You don’t need to say more than that; they’re not supposed to ask for details, and it explains why you left the last job as well as what you’ve been doing since then.