Ask a Manager

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

1. Owner won’t do anything about our terrible employee

I am late in my career and several years ago I was lucky enough to have found the best job I have ever had, at a very successful, very small niche company (8-10 employees). My boss (Jerry, the owner) and everyone I work with have been amazing. I am the office manager/HR and the only woman and only office employee. All the guys do field/shop work. It is a very rough and tumble sort of place, but the guys are great fun to work with and there is lots of mutual respect. We have a fleet of company trucks and are on-site at customer locations five days a week.

About a year ago, we hired a very problematic employee, Ron. He is mean, insulting, and disrespectful to most of his fellow workers. He has tried to work his own hours, comes and goes as he pleases, tells no one when he leaves (we have set shop-time hours). He ignores me unless absolutely necessary. He throws tools in the shop, has a big temper. When riding in company trucks, I have been informed that he gives the finger to other drivers when he feels they have disrespected them. I am also most concerned about what he will say to a customer if/when he loses his temper.

The majority of the other employees have voiced their concerns/filed complaints with me regarding Ron. My pleas to Jerry to terminate him go mostly ignored as Ron has a mechanical ability that is missing in some of the other employees.

The last straw for me was that Ron was recently given a company vehicle to drive. All our vehicles are numbered, for maintenance etc. All of these things run through me. The truck is very prominently badged with company logo, phone numbers, services, etc. I have numbers in stock when new trucks are purchased. He changed the truck number to 069 (it already had a number). He went out and purchased the new stickers. I was not asked nor notified. This truck is running all over five states and our customers see it. When I told the boss about the numbers, he did tell him to remove the numbers, but as of today he has not. New numbers were given to him by another supervisor and his response was that he already has numbers on the truck.

I do want to make clear that Jerry is one of the most outstanding people I have ever met. He is a great guy but we have had multiple conversations regarding Ron that get nowhere and this is very out of the ordinary. Until now, I have had an amazing relationship with Jerry but unfortunately this is making me consider early retirement, as I don’t want to spend my last working years dealing with this guy, but I’m still a few years away. I would love to hear your opinion on this.

For whatever reason, Jerry isn’t going to fire Ron. I don’t know why — maybe it’s really because of his mechanical ability, maybe he reminds Jerry of a loved one, maybe he’s holding his mother hostage, who knows what — but regardless, it sounds like Jerry has made it pretty clear that he’s not going to fire him. Jerry has the same info you do, and he’s not budging. (He does have the same info you do, right? If for some reason you’ve softened anything in relaying the problems, correct that … but I’m assuming for the sake of this response that he knows everything.)

Given that, all you can do is decide if you want the job under those conditions. You might be able to lay down some boundaries, like “I won’t deal with Ron on XYZ so you will have to handle that,” thereby shifting some of the pain of Ron over to Jerry … but mostly, you’ve got to decide if the job is still worth it to you if Ron is part of the package.

Unfortunately, this kind of thing ruins lots of otherwise good jobs.

2. I’m sick of being the only person who can manage our old technology

I work in a large company. I’ve only worked there for around 4.5 years, but due to a big shift in the technology they use, along with a loss of virtually all of the staff who were familiar with the old tech, I am now the only person who knows how to manage the older tech we use.

It’s not insignificant; we’re talking business critical databases, servers, and networking. It has never been part of my job description to manage these, but due to personal interest I learnt from the previous staff, who have now left. Due to the shift in technology, those positions have not been replaced.

I’ve been told by multiple managers that due to this being legacy technology, there is no point training new staff to deal with these systems. However, every project to remove them for the past year has been cancelled due to business priorities. We’re now a year past when I was told that we would no longer require them, but they’re still there and causing me a massive headache as I try to manage them on top of my fairly intensive job working with new tech.

I’m fed up with being the go-to guy for these, I get called out on holidays and out of hours to help with them. My manager is always very generous about giving me double time pay for the inconvenience, but I’m at a point where I am thinking about leaving just so I will not have to deal with old tech any more.

Can I give my department an ultimatum that I will stop supporting these old systems regardless of whether they are still in use? Can I train people secretly to deal with them if I am not available? Or should I just bear it until the business gets around to replacing them?

I love my job and the people that I work with, but I feel caught between a rock and a hard place, trying to balance my real job against the constant support of old systems that I have no formal training with and is not at all part of my job description … not to mention the expectation that I will be available when I am not on call to help out with issues.

You can try — including letting your boss know that they risk you leaving over it, at which point it sounds like they’ll really be screwed — but it’s very likely that you’re still going to get pulled into helping.

But what if you were simply unavailable outside of your normal work hours, even if it causes a crisis? That might be what it takes for them to be moved to finally act. It would be a courtesy to give your boss a heads-up about that change — something like, “My family commitments outside of work are ramping up and I’m no longer going to be available to help with OldTech outside of my normal work hours. If you want me to train others who can be, I’ll do that. But I want to make sure you know I won’t be able to respond if I get calls about it on holidays, evenings, or weekends.” What they do with that info is up to them — and if they don’t take you seriously when you say it, they’re likely to quickly realize it the first time you don’t respond when they need you.

Make sure you document in writing that you gave this warning, though, and consider whether there are others besides your boss who should receive that notification too.

3. My employee never covers other people’s shifts

What is your advice in addressing an associate who will never cover a shift when someone calls in sick? I have a very small staff of three, including myself, in a vision clinic. My other associate will always cover if she calls in, and of course I do. I think it’s very disheartening to my associate that is reliably available if needed.

If she’s otherwise a reliable employee, accept that she’s not available to cover shifts that she hasn’t been scheduled for. That’s not unreasonable of her — if she’s not scheduled, she’s presumably making other plans with that time and it’s not realistic to expect her to just jettison those plans at the last minute.

If you need someone who has regular availability for last-minute shifts, you need to hire specifically for that, making it clear that that’s part of the job so people can raise it up-front if they’re unlikely to be able to do it. But it’s not reasonable to expect that your staff member will always be able to step in at the last minute when someone is out, especially if she’s not being paid for that flexibility. If it’s truly essential, you might have more luck by paying a premium for those shifts or paying someone to be on-call.

4. I retired but keep getting requests from my boss

I recently retired from a state agency. Due to state law, I can’t work for any state retirement system employer for 12 months or I could forfeit my pension.

My former boss keeps calling me about issues in the department. Today she asked me to train her on a complicated task. I feel very uncomfortable with this. The problem is that my old job has not been filled. I gave my notice of retirement in January but the job was not posted until a month before I left.

I spent a lot of time documenting my old job and I feel like I wasted my time, as no one seems to be looking at the procedures. I don’t want to be an unpaid consultant but I don’t want to mess up my relationship with my old boss. I really like her but I feel like she is trying to take advantage of me. There was no discussion before I left of doing any in-depth training. I don’t mind the occasional question, but I don’t want to spend hours doing my old job for free. I am not sure how to address this.

In response to the latest message, wait a week and then send this: “Just saw this. Between family and other commitments, I’ve got no time these days — sorry I can’t help. But I documented everything before I left, and there should be useful info there.” Wait a week or longer before responding to any future messages too; she’ll learn to get her answers elsewhere.

Alternately, you could just explain that you’re not willing to do anything that could jeopardize your pension (“it was made really clear to me that I can’t answer work questions once I retired or I could lose my pension — sorry I can’t help!”) but if there’s any risk of her trying to say that you’re wrong about that, go with the first option.

5. Should I list two colleges when I only graduated from one of them?

I attended four years at a university but did not graduate. I have been up-front with employers about my not having a degree. After a long break, I went back to school, a different university, and officially now have a bachelor’s degree. I am in the process of updating my resume and am unsure of what to do with the other university. Do I leave it on there? In the past, I have left it just with the dates and no note about a degree. But now that I have the degree, it feels like I should remove the previous institution. Am I thinking too much about this?

Yep, remove the first school since you didn’t graduate from it and just list the one that you did graduate from. When you attended multiple schools but only graduated from one, typically you only need to list the degree-issuing institution. You can list the other if you want to, but there’s no need to. (In a different set of circumstances, you might decide to leave it on if it strengthened your resume — like if you wanted to be able to show you completed a large amount of coursework in Relevant Area X — but otherwise there’s no need to.)

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

1. My employee forgets half of what I ask him to do

I have an employee who’s a direct report (my first) with a couple of quirks, but none that causes more issues than this: he just doesn’t listen. I’ll list off five or six things he needs to do, change on a project, etc., and he’ll come back an hour later with three of the things done and ask if it’s good to go. I’ll remind him of the other items on the list, and he’ll usually respond, “Oh right” and goes back and completes the list. This happens almost every day.

Is it something that’s a real issue or am I just being too hard on him? It frustrates me that he wastes time by not completing all the items in one go and thus interrupts workflow more often. He’s on the younger side and this is his first professional job; I genuinely can’t tell if he’s being lazy or is just that forgetful. Even when I tell him to write things down, it makes no difference. I’m tempted to sit him down and explain that when he doesn’t take the time to be thorough and make sure his work is done before presenting, that it comes off as apathy towards this job and like he’s rushing just to get done with it. Is this something that warrants a conversation? Is this just the universe teaching me a lesson in patience?

Yes, you need to talk to him! Whenever you have concerns or frustrations with an employee that the employee doesn’t know about, you are falling down on your job as their manager.

In this case, you should start by naming the pattern — “I am finding that when we discuss your projects and I give you a list of, say, five items to complete, you’ll often only complete two or three of them. I need you to make sure you’re writing down every action item that’s assigned to you when we talk, and that you’re checking your work against that list before you submit it.”

In addition, try having him repeat back to you his takeaways before you both leave the conversation. For example, at the end of a conversation where you’ve assigned him work, you could say, “I think that’s everything. To make sure we’re on the same page, can you run through your understanding of next steps from here?” It’s surprising how often doing that will reveal things the person missed or areas where something was miscommunicated, and it’s a good way for you to make sure you were as clear as you thought (sometimes you won’t have been!) and for you both to make sure he’s not missing anything.

Note that with all of this, the focus is on the specific things you need him to do differently. It’s not about interpreting his behavior (such as with your thought that he’s being lazy or apathetic). As much as you can, stay away from telling yourself that kind of story about an employee. Focus on the behaviors that are actually happening and what you need to see instead; it will make your job a lot easier and less frustrating, and it’ll make you a better manager to work for.

2. My coworker swore at me in a reply-all

I work in healthcare. We have a roster email each day, detailing staff assignments, who called out, etc. Our manager is terrible at updating it. Often the “line staff” will send a reply-all email to update if staff have left early, etc. I did this very thing last week and another coworker with my same job title replied all with, “fucking idiot.”

I went to my manager, my manger’s supervisor, and HR. This culminated with me being called into a surprise immediate meeting with the offending coworker, my manager, and my manger’s supervisor. The offending coworker said she sent the email as a mistake. She didn’t apologize, just described that she was running late and had “personal things going on” and mistakenly sent the email. The head supervisor then asked if I had anything to add and if no, to “wipe the slate clean” and get on with our Wednesday.

This colleague is often unprofessional, hostile and rude (all of which I described to HR). Was this handled appropriately in your opinion? Is this the standard of behavior in workplaces now and I just need to expect it and deal with it?

No, it’s not standard behavior at work. But you wouldn’t necessarily know about it if they also had a more serious conversation with your coworker, which they certainly should have! It’s pretty common not to handle discipline in front of other employees, and for all we know, they could have had a very serious conversation with her where they made clear how out of line her message was and that it couldn’t happen again, and then called you in for the end of that meeting to try to get you both to move forward.

The bigger issue is the pattern — that she’s often unprofessional, hostile and rude. If you’ve brought that to your management’s attention and nothing changes, the problem is much more with them than it is your coworker.

3. My partner is uncomfortable taking a plus-one to a public event

My partner works in a field where members of their team are regularly invited to various events. Sometimes they’re closed events where the team has what are essentially press passes to gain special access, other times they are public events where anyone could buy a ticket and attend (think red carpets, comic-con, sporting events, expos, etc.).

There’s a big event coming up in our city, and my partner just got wind that they may get a ticket through work. This will be the first time this industry has held an event here and it’s being pitched as the first of its kind. I’m by no means the biggest fan or target audience of the industry, but the topic has always been a huge hobby for my family and I am excited about it! It feels like a historic event that I want to experience.

When my partner has gone to events with work before, they’ve typically either been in assigned seating together, or in a restricted area that the general public can’t purchase access to, and team members don’t bring plus-one’s or partners. This event, however, is general admission so I could theoretically buy a ticket and attend just like anyone. Would that be weird or inappropriate in any way? I’m really torn and don’t want to make my partner uncomfortable. They’re a step above junior level, being invited by directors, and I understand they may need to be “in work mode” here and there to thank a client or network, but ultimately these events are known for being loud and rowdy (beer! music! etc.!) and nobody will be discussing serious business. I really want to go!

I can tell my partner is a bit uncomfortable being seen as inviting a plus-one to a work outing, but is that how it would be seen? Can I buy my own ticket and go? If I do, should my partner mention it to their team? Can I hang out with them, or do I need to make myself scarce? None of my friends are interested in this industry, and tickets aren’t cheap, so my options are to hang out alone or with my partner and their team. I admit I’m feeling a bit jealous because my partner has only gotten into this hobby because of my family’s and my interest so my judgement may be clouded. What do you think?

Let your partner make the decision; they’re in a better position than you or I am to assess it. In a lot of cases, it would be totally fine for a partner to show up for an event like this. But if the norm in their office is that partners don’t attend, I don’t blame your partner for feeling awkward about it, especially as a more junior person who’s trying to impress their directors. And if it’s a work event for them, I’d want to prioritize their comfort in a professional situation.

That said, would they be comfortable with you attending completely separately — buying tickets separately, sitting separately, and each pretending the other isn’t there? If you’ve been pushing the idea of going together, I think you should defer to your partner’s judgment on whether or not that’s a good idea. But if you can just happen to be at the same event, while not attending together, it sounds like it should be fine.

4. Levering another offer when you’re negotiating

Can I leverage a second job offer to negotiate the first? I really want to work for one company, but I really need the additional salary that the other is offering. It’s a $10k difference. Even just an extra $5k/year would help me out.

It can be done! You need to be careful to sound like you’d prefer their offer but are grappling with the money. For example: “I’m really interested in this job and would love to accept. I have an offer for a position that pays $X but I’d prefer to work for you. Is there any way you could match that or come close?”

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

1. Should I leave my job with great benefits but a problem boss?

I need some help figuring out if I should stay in my current accounting job, or if I should start job searching. I work for a pretty small business, about 80 people across four locations. The office I work in has eight people, including the two owners. The good things here are very good, and the bad things are pretty bad. I only started here five months ago (but I have a solid work history, so I’m not super concerned about leaving soon if I need to).

Here are the good things: I am essentially working part-time for full-time pay and benefits. The owners overstaffed this role so I’m working about 15 hours a week making a competitive market salary for a full-time role with my title. I get to completely set my own schedule, come to the office when I feel like it, and work remotely when I feel like it. I don’t deal with any clients, so I truly can just work whenever I want as long as all the work gets done in a timely manner. Some days I start work at 7 am, and some days I don’t start until 4 pm, depending on what I need to get done in my personal life. The owners are only in the office about 15-20 hours a week and don’t monitor us at all. I have unlimited PTO and the owners really let us take advantage of this benefit. People routinely take 6-8 weeks off a year, including the owners, and no one gets any flack for it so long as work is done. My husband and I are actively trying for our first baby, and I genuinely don’t think I could find this work/life balance and level of flexibility at any other company.

Now the bad: When I was hired, the owners were honest with me that they weren’t 100% sure why I was being hired. They explained that the person working in the finance department already was overwhelmed, and they didn’t know if it was due to business growth or because she couldn’t handle the workload. It became immediately apparent to me that she just couldn’t handle the workload, so this department is overstaffed (hence why I’m only working 15 hours a week, sometimes less). When I mentioned this to the owners, my manager explicitly told me he knew we were overstaffed, but he planned on making no changes. This colleague, “Marissa,” has more education and experience than me. But she’s making my life hell. She’s a very nice, friendly person, but doesn’t understand even the basic concepts of our type of work. She is routinely going through my work and changing it (even though she’s not my manager) and screwing it up so I’m constantly redoing work. When I explained what was going on to the CEO, he told me it was my responsibility to handle “personality conflicts in the workplace” and that he “doesn’t know enough about what I’m doing to determine who’s right.” Because our CEO has zero knowledge about my type of work, when I try to explain things to him, he gets angry if I don’t do things the way he wants. For example, he constantly wants me to change our financial statements in ways that are not legal. When I tell him the changes are not permitted under IRS rules, he calls me insubordinate and sends me home. My name is signed on those financial statements, and if we’re ever audited, I’d be the one at risk. Also, I feel like my skills are atrophying already, and my sense of norms are being warped. My manager yells at people and everyone here just acts like it’s normal. I’m doing so little work that it feels like I’m not growing or progressing at all.

Do the benefits outweigh the drawbacks, or is this a cut my losses and run scenario? If it makes a difference, while I do want flexibility in my career so that I can start my family, my husband is going to be a stay-at-home father, so long-term my career success is more important for us than my ability to be really flexible.

If it weren’t for your CEO pressuring you to break the law — and calling you insubordinate when you explain you won’t! — I’d tell you that this just comes down to what you personally value most: flexibility versus satisfying work and professional growth. There’s no right answer to that; it depends on what’s most important to you. Some people would love the situation you have (minus the legal issues), even with the Marissa situation, and others would be itching to get out. It’s a personal call.

But the legal issues and the CEO’s handling of it tilt the scale to “get out.” That’s a serious situation that could have legal and professional ramifications for you even after you’ve left this job and it’s not worth it, even for the very real benefits you’re getting in return.

2. Coworker has a quote about weapons in their email signature

I received an email from someone who works for my company but in a different location, and they had a TV show quote in their email signature. Normally I wouldn’t have thought twice about it but the quote was from The Mandalorian: “I’m a Mandalorian. Weapons are part of my religion.”

I should add: we work adjacent to higher education. I feel like referencing weapons even in a quote from a show is probably in very poor taste!

I’ve obviously never met this person and I’m not sure about what, if anything, I should say to them about it. Thoughts or advice?

WTF? That’s wildly inappropriate in a work context. In an era of workplace violence, it’s outrageous that (a) someone would think this was a good thing to put in their work email signature and (b) it hasn’t already been swiftly dealt with.

Forward it to HR or whoever plays that role in your company with a note that you were alarmed to see it and hope they’ll ensure it’s removed. Don’t engage with the person directly about it; they might just say no, so you need someone with the authority to handle it to handle it. (Ideally that would be their boss, but I’m suggesting HR instead because I assume their boss has seen the email signature by this point and for some reason hasn’t found it worth addressing.)

3. I don’t want people to think my pronouns and time zone are part of my name

I’m a director at a fairly progressive company that’s predominantly remote. Recently, the powers that be dictated that everyone is “encouraged” (read: “you have to do this”) to add their pronouns and time zone to their name in Slack. I don’t want to do this! My name isn’t “John Doe (he/him) (PST),” it’s just “John Doe.” There’s no bigotry angle here, as I already have my pronouns and time zone in my Slack profile and did so willingly before I was asked to. I have a real problem with my name being presented as anything other than my name, but I’m worried that not doing this will be interpreted as some sort of political stance when it’s not. Is my only option to bite the bullet and do it even though it bothers me on a personal level?

Yes, it will definitely be interpreted as a transphobic stance even if you don’t intend it that way, because what you’re saying doesn’t make sense any other way. No one is going to think your name is “John Doe (he/him) (PST).” It’s going to be obvious that that’s your name, your pronouns, and your time zone. It’s no different than if your company wanted you to include your job title after your name in your email signature, as many do — no one is looking at “John Doe, engineer” and thinking “engineer” is part of your name.

So the good news is that you don’t need to worry about that at all! You can include your pronouns and time zone without any risk that they will appear to be part of your name.

(If “encouraged” truly does mean “required,” though, that’s a problem since it can force people to out themselves or declare pronouns they don’t identify with. Encouraging it is good; requiring it isn’t.)

4. Can I mention the work I do for my disabled spouse on my resume?

I’m a carer for my disabled spouse — not formally or legally recognized, but in practice I do an awful lot of administrative work, scheduling, advocacy, research, and communication on their behalf. This has definitely helped me develop and demonstrate significant experience in all these skills, but I’m not sure if it’s something I can or should include on my resume or job applications. I’m concerned that employers might worry that my role as a carer might impact my attendance or performance. And if I were to include this experience, I’m not sure where or how to do so! I’d really appreciate any advice you have on this.

Leave it off. In general, work that you perform for your household or family doesn’t belong on your resume — partly due to convention, but in larger part because there’s no way to assess how well you did it. If you frequently dropped the ball, were horribly disorganized, and regularly messed things up, a prospective employer would have no way of knowing that … and there’s no appropriate way for them to probe into it. Plus, your family members can’t be references for the work (and they’re also much less likely to fire you than an employer would be!).

5. Helping an intern with the transition from intern to employee

I work for a small nonprofit where I’m the only full-time staff member (my boss, our executive director, works part-time and on a volunteer basis, so I’m the one running things day-to-day.) We’ve had a paid internship program for about a year and a half now, and it’s been great. One of our interns (Greg), who has been with us since the internship program began, will be coming on as a full-time staff member in a few weeks. I’m thrilled, because Greg is fantastic and a perfect fit for our organization, and having him on full-time will really help take stuff off my plate and help our organization grow.

I’ve onboarded new hires before, but since Greg has been working here for over a year (and honestly operating much more like an employee than an intern, in terms of the level of ownership he’s been able to take on), I know that the onboarding process should be a little different than it would be for someone who’s totally new to the organization. Do you have any recommendations for how I should structure Greg’s onboarding into this new role and what that onboarding should include? Is it just the typical onboarding process minus the “here’s how our organization works” part? Are there any other things I should incorporate to help him transition smoothly from a part-time intern to a full-time staff member?

Do all of it, just like you would if he were brand-new to the organization — because there are probably holes in his knowledge about how your org works that you don’t know about (and that he may not even be able to identify). In fact, although it wouldn’t be practical, I sometimes think there would be benefits to re-doing new employee orientation once people are six months in, because everyone misses a lot in the beginning.

You can explicitly tell him your plan at the start — “I’m going to go over everything with you that I normally would with a new hire. Some of this will be familiar to you, but I want to make sure you don’t miss out on anything just because you’ve already been interning with us.”

In addition, think about what’s changing for Greg now that he’s moving from intern to staff. What expectations will be changing? Are there things he didn’t have the authority for previously that he will have now? Do you want him to manage his work any differently? Step up differently in certain areas? Whatever those things are, spell them out explicitly. (That said, generally you won’t be able to anticipate all of those little changes, so assume you’ll be naming some as you realize them, too.)