The Workologist: When a Subordinate Is Friends With the Boss

You might wish you could put a stop to a suspiciously chummy office relationship — but you can’t. Instead, you need to figure out a way to manage around it. Here’s how to proceed.

CreditMaria Nguyen

Send your workplace conundrums to, including your name and contact information (even if you want it withheld). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

I recently joined a tech start-up (with 70 or so employees) in a management position. I have noticed that my boss goes on morning and evening walks every day with one of the people who reports to me.

It makes me uneasy that a guy who reports to me is chumming around with my boss — especially because I know he is a bit of a chatterbox and a gossip. These walks, and the pair’s apparent closeness, make me a little hesitant in giving an honest performance appraisal of this worker who I am supposed to manage.

It also makes me nervous that these two may be discussing a lot more stuff behind my back — and maybe about me.

Am I justified in feeling a little peeved? How do I overcome this?


That sounds annoying and maybe even a little weird. (Two walks every day?) But your first step is to avoid turning this into a bigger problem than it probably is by conjecturing nightmare possibilities.

Peeved as you may be, it’s unlikely that you can change this relationship, whatever it actually is. You’ll ultimately need to figure out how to manage around it. While it may be wise to take care what you say in front of your chatty subordinate, that’s a short-term solution.

Your second step is to get some facts, while screening out distracting speculation. You might start by asking around among your colleagues or other managers. Don’t overdo this: You don’t want to come across as if you’re launching some paranoid investigation. But I can’t imagine you’re the only one who has noticed the behavior, so simply floating an innocuous query — “Those two seem close. Are they old friends?” — by someone you trust will likely get you some basic answers.

And soon you should probably have a straightforward, low-key conversation with your boss. Not panicked or accusatory, “What are you guys talking about?” Just make a casual inquiry. Mention that you’ve noticed that they seem close and ask if they were colleagues together elsewhere or know each other socially.

Frame this as basic professional curiosity: You are, after all, a manager learning the dynamics of a new company. Ask in an open-ended way and hope that the response yields useful context. Who knows, maybe you’ll learn that they don’t talk about work at all, but rather some other shared interest.

Ideally, your boss will realize, without being bluntly informed, that this situation might trouble you, and will promptly set you at ease. But even if that doesn’t happen, what you want is to shift from a state of being concerned to one of being informed.

If some specific problem really does emerge — a performance issue with your employee, for example — you’ll be better prepared to make a case that sticks to the business at hand, whatever this pair’s relationship may be.

CreditGracia Lam

Does Asking for a Chair Seem Entitled?

I recently started an internship with a company where I hope to work some day. The other interns and I work from laptops, while seated on stools around a communal table.

I have a chronic, not-visually-obvious shoulder condition and doing computer work without arm support hurts, a lot. I’d like to request an office chair with arms, but I don’t want to appear entitled or weak to my supervisor or colleagues. Do you have any suggestions?


Yes, I suggest that you explain your condition and ask for a chair with arms!

It’s hardly an extravagant request, and you are indeed “entitled” to get through your workday without being in pain.

I’m not sure I see the point of making all the interns sit on stools in the first place: Is it explicitly meant to underscore low office status? I hope your employer reacts by giving everyone a real chair.

For readers who may be curious about the legal context, there are two issues at play.

The first is whether a worker with such a condition could get an accommodation under the Americans with Disabilities Act. In most situations the answer is yes, according to Carol Miaskoff, associate legal counsel at the Equal Employment Opportunity Commission.

“The limitations don’t have to be radical to be considered a disability,” she says, and company policy ought to enumerate details such as what sort of medical proof would be required.

Second, while this may vary by state or other circumstances, if you’re an unpaid intern you most likely don’t have the same rights as an employee. (This discrepancy is a much-debated topic at the moment, Ms. Miaskoff adds.)

Strictly speaking, however, I’d say none of that should be relevant in this case. There’s no need to invoke legislation; all you’re asking for is a chair.

Unless your fellow interns and your bosses are monsters, they won’t begrudge you this simple relief. And if I’m wrong about that, you don’t want to work for these people — so you might as well find out now.

Vocations: When a Colleague Takes a Parking Space for People With Disabilities

Two colleagues seem to be using parking spots they don’t deserve. But deciding whether to bring this up with management depends partly on sorting the facts from rumors — and dubious assumptions.

CreditMaria Nguyen

Send your workplace conundrums to, including your name and contact information (even if you want it withheld). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

At my office, there are two employees who park in parking spaces for people with disabilities on a daily basis. Both have placards hanging from their rearview mirrors.

One of the employees has revealed that the placard is for his daughter, but he uses it all the time, even when she isn’t with him. The other employee doesn’t appear to be disabled in any visible way, and talk around the office is that he abuses a space, too.

Both employees work in the same department. Is it fair to bring this matter to their boss’s attention?


The two cases you describe are actually distinct in important ways. I’ll address the latter first. Reporting a colleague to management based on unproven office scuttlebutt is rarely a good idea, and seems particularly inadvisable here. Just because someone doesn’t appear to have a disability doesn’t mean he or she might not qualify for a disabled parking permit.

At the federal level, the Americans with Disabilities Act sets a baseline for the availability of these spaces, and the Department of Transportation’s Uniform System for Parking for Persons with Disabilities lays out basic rules for who is eligible to use them, according to Rabia Belt, an assistant professor at Stanford Law School who focuses on disability and citizenship.

Certain cardiac, respiratory, arthritic or neurological conditions that limit someone’s mobility or ability to walk — even if they do so in ways that aren’t immediately visible — can easily qualify. (There could be additional qualifying conditions under state laws.)

Ms. Belt points out that an unfounded suspicion that lots of people take advantage of disability benefits by “faking it” is not uncommon. In fact, one of her graduate students is studying perceptions of “disability cons” for his dissertation.

“This can be a really big problem for people who do have disabilities,” Ms. Belt says. People with legitimate but not immediately visible disabilities get accusatory notes left on their cars, or are conspicuously photographed by apparently suspicious strangers in parking lots. And, she adds: “They have to deal with this gossip behind their back.”

In short, if you don’t actually know whether this colleague is misusing a permit, I’d say leave it alone.

But what about your colleague who, apparently, openly admits to a disability con? Well, if true, he’s definitely a jerk, and should be ashamed of himself. How would he feel if he took his daughter somewhere and couldn’t get the parking space she needed because all the spots for people with disabilities were taken up by cheaters like him?

Still, if you want to bring this to management’s attention, frame it as a management issue. Let’s say you yourself have a disability, and can’t use your space because of this guy. In that case, you should absolutely take action. Or if you believe other employees or visitors are similarly denied a space they deserve, that is also an issue management should legitimately want to know about.

Of course, you can also point this behavior out to the bosses because it just feels wrong and offensive: Even if he has never denied someone a space, he could, and that’s enough.

You just don’t want to come across as simply ratting out somebody who bugs you, or you’ll seem like a busybody and the problem may not be taken seriously. That doesn’t mean you shouldn’t complain, you’re just better off reporting it as a company problem, not a personal one.

CreditGracia Lam

Bothered by Service Worker Language

I’m bothered by people I encounter in a variety of service jobs (like bank teller, waiter, cashier) who wish me to “Have a blessed day.”

I know they mean well, but I find this offensive. What would be an appropriate reply? Do you recommend advising the employer about this behavior? I wouldn’t name names or even identify a particular branch/location.


I think you’re right that these people mean well — and I’d try to focus on that.

It’s not clear to me how reporting the described behavior in such an abstract way would achieve anything. The more practical alternative would be to get specific: Report it directly to a manager, with the explicit threat of taking your business elsewhere.

Would that be worth it? Maybe if a bank teller (or whoever) followed up this anodyne statement with aggressive proselytizing, or demanded, “Don’t you want to wish me a blessed day?,” then you would do management a favor by pointing out that a front-line service worker seems to be prioritizing an agenda that isn’t the company’s — and likely alienating customers in the process.

It would also be worth complaining if you are truly offended and this is a matter of principle. That’s a personal decision, but if you’re going to do it, be direct.

If you’re really just irritated, then I think the most appropriate response, delivered in the strictly neutral tone of polite indifference that is at the very heart of what makes a marketplace work in a vibrantly diverse society, is: “Thanks.”