my boss is having memory issues, coworker watches videos without headphones, and more

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

1. I’m drowning at work because of a family situation — how do I talk about it?

My father passed away this past summer from pancreatic cancer. The complications of his illness had slowly escalated throughout the year prior, and I needed to take increasing amounts of time off work to fly to my parents’ home across the country.

I work for an extremely small nonprofit and am in a director role. My work is project-based and I report to the board. No one keeps track of how much I’m working and when; they only care if the projects are done on time and well.

The summer is our “off” season, and it’s when I usually get the bulk of my project work done for the busy season. This allows me to take care of more urgent/time-sensitive tasks during the year, and gives me the time to plan for future years.

Unfortunately, due to the time commitment and mental load of last summer, I was unable to complete my summer project work. This has resulted in a very stressful situation where I am still working on my summer project load throughout the year while simultaneously doing the day-to-day urgent tasks on top of planning for the following year. It has been a domino effect of work piling up to amounts that are untenable. I feel like I’m trying to stem the tide of an entire ocean with a bucket of water.

Miraculously, despite missing most of my internal deadlines, I have managed to complete my previous projects on time and received satisfying feedback from the board. However, I am now approaching the final project and have missed three internal deadlines, and now I am missing external deadlines on deliverables, and people are noticing. It is affecting other people’s jobs because I’m unable to deliver what they need in an adequate time frame due to not having enough hours in the day. I think (hope) I’ll pull the project off in the end, but it is at risk.

I have told a few people I trust that this is a result of what happened over the summer, but I don’t feel comfortable telling clients who I don’t know very well that I’m missing deadlines due to my father’s death nearly nine months ago, even though it’s the truth. And of course, there’s the part of me that feels like nine months should be enough time to get my shit together, and I shouldn’t be struggling this much.

I think I need a reality check, and some solutions. I am the only person in my org who can do what I do, so there’s no staff to delegate to. But I think I need to start letting people know that I’m struggling. Is it valid to give the real reason? Is this even a good reason? How do I stem the tide?

Yes, this is a good reason. You had a terminally ill parent who died.

It’s completely reasonable to say, “I had a terminally ill parent last year and spent a lot of time dealing with that situation over the summer, when normally I would have been getting a lot of work done in preparation for our busy season. I’ve been trying to catch up ever since, but I’m at the point where I need to reassess what’s on my plate so that people aren’t counting on me for things that I literally have no time to deliver.” You’d say that to whoever on the board you work most closely with.

Have that conversation first — because “just do it all in significantly less time than it actually takes and in significantly less time than you’ve been able to spend on it in the past” is not realistic or possible (as you’re seeing). Then from there, decide what the message needs to be to clients — presumably some version of the first part of that, but instead of “reassessing what’s on my plate,” you’d tell them what the results of that reassessment mean for them, which could be anything from, “I’ll be able to get you X, but not until June” to “Jane is going to be your contact on X for the rest of this year” to “We need to put the X project on hold this year.” But have the bigger picture conversation with your boss first, because the actionable pieces for everyone else will stem from that. And start that process now, because the longer you wait to make (and tell people about) these adjustments, the more inconvenient it will get for them.

I’m sorry about your dad.

2. My boss is having memory issues, and I’m worried it could become malpractice

I work in a very small law firm in a support role and have been here for six years. The founder of the firm is older and is demonstrating some concerning changes over the last year that make me worried there is some kind of cognitive decline. He is only in his mid 60s.

At first, the signs were subtle: missing calendar invitations, falling behind on email, etc., which could be explained away by being overly busy. Then, it turned into forgetting how to use case management software we’ve been using for years, forgetting names of people with whom he has represented several times, and even once missing a court filing deadline. Sometimes, he will completely forget to update a client on their case, so they call me frantic for an update. I’ve also noticed a shift in patience. He seems much quicker to frustration than he used to be and is firmly rejecting new ideas. Everyone has noticed, but no one has said anything. We do not have HR.

He’s the best boss I have ever had, but the trend is concerning and is starting to affect his clients, which could be considered malpractice. I don’t want to report him for malpractice because that would make the issues he’s experiencing very public (not to mention would jeopardize my career), but he is not fit to represent clients! Attorneys wield a lot of power, so I don’t think I can stay quiet longer, and I know this is an issue with aging attorneys nationwide. I’ve been working in the legal field for a good chunk of my career, and it’s my observation that attorneys are a lot more receptive to feedback from other attorneys, not legal assistants (like me). Anytime I’ve tried to bring it up with another coworker, they brush it off, so I’m not optimistic I could get support from colleagues to approach him as a group, which is often your advice. How would you proceed? What’s my obligation, if any?

Are there other attorneys on staff or is it just him? If there are other attorneys on staff, can you have a discreet word with the one you most trust to navigate this?

I asked employment lawyer Jon Hyman of Wickens Herzer Panza, who writes the Ohio Employer Law Blog and is the author of The Employer Bill of Rights: A Manager’s Guide to Workplace Law, what you can do if the firm doesn’t have other lawyers. He said, “Once missed deadlines, forgotten clients, and basic functional breakdowns occur, the issue stops being internal and becomes a client protection problem. As a non-lawyer, you don’t have a formal duty to report misconduct. But you’re not exactly free to ignore it either. Law firms rely on staff not to silently enable conduct that risks client harm, and when something goes wrong, everyone involved gets pulled into the fallout.” He agrees with you that this is a message your boss is far more likely to hear from another lawyer and suggests, “Identify a single attorney he respects and share concrete, client-focused concerns. That’s not ‘reporting’; it’s responsible escalation. At the same time, push for structural protections: redundant calendaring, standardized client updates, and pre-filing checks to reduce risk.” If nothing changes and clients remain at risk, “You can report concerns to a state disciplinary authority — anyone can — but that step is typically a last resort given its seriousness and potential consequences. It becomes more appropriate when there is ongoing harm and no internal response. Some jurisdictions also offer confidential lawyer assistance programs that may provide a less punitive path.”

He also says, “Focus on observable patterns like missed deadlines, communication lapses, and confusion, not speculation about causes. If you raise concerns directly, frame them around client service and support, not decline. The goal is to assess awareness and openness to safeguards.”

3. My coworker watches videos without headphones

In December, I started volunteering behind the bar at an arts venue. I enjoy the work and get along with most of the people there. Perhaps most importantly, I feel genuinely accepted, which is very different from most of my experiences as an autistic man in my part of the world.

One of my fellow volunteers, a man I’ll call Fergus, who is my peer but has been here longer than I have, has a habit that really annoys me. Every break without fail he watches TikToks, YouTube videos, and the like without earphones in our shared de facto break room. In other circumstances, I would politely ask him to use headphones, but I’m concerned that my status as a relatively new volunteer may make this fraught. Additionally, I otherwise get on very well with Fergus and don’t want to jeopardize that by being too assertive.

Additional context:
* Fergus has been spoken to about this by at least two different volunteers in my presence, both of whom have been volunteering longer than me. He always complies with their requests. I wonder if the fact that I haven’t this far asked this of Fergus means he assumes I don’t object.
* Fergus and I are both visibly neurodivergent men in our twenties.
* I am white and Fergus is not. (Ideally this ought not to matter but I’m conscious that this could engender social dynamics that I may not be aware of.)
* The content he listens to isn’t in and of itself problematic (religious, overtly political, NSFW, etc.).

With all this in mind, how assertive is it appropriate for me to be? My gut feeling is that politely asking him to use headphones is probably the best route, but would it be worth waiting a few weeks to press the matter? Or do I just need to “suck it up” and suffer in silence?

You’ve been there since December; you’re not so new that you can’t say anything! I agree it made sense to be more hesitant as a brand new volunteer the first time you shared a break room with him, but it’s been a few months. It’s completely reasonable to politely say, “Would you mind using headphones while you listen to that?” This would be fine even if you hadn’t seen others ask it of him, but the fact that you have should give you additional confidence that it’s an okay request to make and he won’t be shocked by it.

Go ahead and reclaim your break room peace.

4. Should I send an unsolicited recommendation for an intern?

Would it be okay for me to send a positive job reference without the applicant asking me?

My workplace has a student worker who wants to pursue the same career as me and is applying for an internship I told her about in that field. I’m not her boss; her supervisor is in my department but with a different job, and that’s mainly the work the student has been doing. But I’ve been able to borrow her now and then to let her learn more about my work and to help me, and I can tell she’ll be good at it.

Would be appropriate for me to email the internship place and put in a good word for her, even though I’m not her direct supervisor and she didn’t ask me to? I’m fond of her and proud of her and want her to succeed. I think this is the first time I’ve been senior enough in my career to be in the position of helping a junior.

Do you have any contacts at the place where she’s applying for the internship? If you do, you absolutely should contact them on her behalf! If you don’t … well, you still can, and if it’s a particularly glowing note (not a generic one), there’s a decent chance it’ll get her application a closer look. Just don’t do this.

5. Should I not turn on call screening when I’m job searching?

I recently applied for a job, mainly out of curiosity about the pay range I could potentially be offered as I am not really looking to leave my current job. I checked my application status on the online portal a couple of times and recently noticed it was changed from “under review” to “no longer under consideration.”

I am wondering if the (relatively recent) call screening feature from Apple may have blocked a call or otherwise screened it out? Do employers have a process for getting around the call screening? Or is having it enabled considered unprofessional? If someone is job searching should they ensure that this feature is disabled?

It’s possible that your phone blocked a call, but it’s more likely that they simply decided not to move your application forward.

On the call screening feature — which asks unknown callers to record their name and purpose for the call, then shares that with you so you can decide whether to answer — employers calling you will generally just proceed through the prompt. It’s not considered unprofessional to have it on. (That said, I would not turn on “silence unknown callers” if you’re job searching; that’s much more likely to cause you to miss calls from employers and recruiters.)

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