firecat

Posted by Ask a Manager

https://www.askamanager.org/2026/06/asking-junior-staff-to-speak-for-their-generation-i-dont-want-a-bridal-shower-and-more.html

https://www.askamanager.org/?p=33634

Happy Juneteenth! Here are some past letters that I’m making new again while I’m off for the holiday.

1. Asking junior staff to speak for their generation

Any suggestions for how to curb the need some of my colleagues have to use the “youth” in the room — be it younger staff or interns — to speak for all people of their demographic? This happened to me when I was an intern and I hated it since it felt reductive. Now that I’m further along in my career, I feel like I have a chance to make a change, but I’m not sure how to tackle it.

An example is when we’re discussing a social media campaign video as a group and a member of staff turns to the 20-something intern and asks, “What does YOUR generation think?” then laughs.

It’s pretty casual right now and limited to two particular members of the team, but still feels inappropriate. I want people to realize we respect everyone for their opinions and expertise, ones that do not rely on age or social status, and that one person’s thoughts on a matter do not scale up to represent an entire demographic. It’s infuriating and diminishes the person’s opinion to the year they were born, not experience.

Yeah, that’s annoying — and treating an entire demographic as a monolithic block is rude. That said, it’s also pretty natural for people to see “youth culture” as something they no longer understand or relate to, and to be curious for the young people they do know to explain aspects of it to them. In other words, you may not be able to shut it down in every situation, but you can try.

One way to do it: The next time it happens, you could jump in and say, “I don’t think any of us can speak for our entire generation, but I’m interested in hearing Jane’s take as just herself.”

If someone is a repeat offender and you have the standing to speak to them about it privately, you could do that too — something like, “I’m sure you didn’t mean anything by it, but when you ask our younger staffers to speak for their whole generation, it puts the focus on their age in a way we wouldn’t do with people who were older. It used to make me really uncomfortable when I was younger and people would do that. It’s great that we’re asking for their input but I think they’d feel more respected if it we didn’t tie it to their age.”

– 2019

2. A recently-fired employee was regularly looking at another employee’s burlesque pics online

We terminated an office employee this week who was always just kind of creepy and walked the line of inappropriateness with his jokes. He was fired for something else, not because of any complaints.

Today I went through his computer because a) we need a lot of files from it b) he didn’t password protect it c) we need to know what websites he has work accounts for, etc. But oh man, he didn’t log out of or delete his browser history. As I was looking through his Chrome history to see what websites he frequented for work, I discovered that he found a coworker’s – who does burlesque – web page which has ALL KINDS OF nudey pics in it. He was regularly looking at these photos of her. This is not necessarily on his work computer, but likely his personal phone because Chrome syncs browser info. So it’s not necessarily about company property. (I also saw numerous porn sites and google searches for steroids, and I was only looking up til Dec 1.)

But the thing is … I should tell no one, right? Because he’s already fired? And because maybe the burlesque coworker gave him the link? I definitely don’t tell any bosses, and I maybe don’t need to say anything to her? I don’t want her to be in trouble. If I say something to her, it can still be considered sexual harassment, even if I’m just warning her? But no need to tell her because what she doesn’t know won’t hurt her? And she has it out in public because she wants to?

We don’t have permanent, on-site HR here, but our “home office” has acting HR people that we don’t communicate with much. I just … tell no one, right? Or document it somehow?

Tell your coworker. Maybe she gave him the link, or maybe she didn’t and would want to know and have the option to lock it down. It’s not sexual harassment to alert her to this (presumably you’re not going to be leering and making provocative comments about her photos and so forth!). You can simply say, “I wanted to let you know that when I was clearing out Bob’s computer, I found he was regularly looking at your burlesque page. You might be totally fine with this, but in case you weren’t aware of it and wouldn’t want coworkers accessing it, I wanted to give you a heads-up.”

I’m not suggesting that you seek advice from HR on this because I don’t want your coworker to deal with any hassle from them, and it could end up playing out that way. So just a simple heads-up to her, and then move on.

– 2019

3. Coworkers are planning a weekend bridal shower for me and I don’t want to go

I have a (good) problem in that my coworkers are friendly and generous. I’m getting married in the fall, and my coworkers apparently decided amongst themselves to throw me a bridal shower.

The problem:
1) I do not consider these coworkers to be my friends outside of work. That wouldn’t be a huge issue if this was a bridal shower held during lunch or happy hour BUT
2) It’s being held in a different town at a coworker’s house.
3) I don’t have a car because i live in the city, and it’s going to be a two-hour round trip for me ON A SATURDAY to go to a bridal shower in the suburbs that I never asked for.
4) None of these coworkers have been invited to the wedding, and I am happy to chat about my wedding at work as part of small talk, but I am not really interested in having my coworkers be part of any of the wedding or pre-wedding activities.
5) They’re both very conservative and religious, which is fine! But my idea of fun outside of work (pub crawl, bawdy jokes, team sports etc) does not align with theirs — sitting around, eating cake and making small talk about our families.
6) They’ve all asked their work friends to attend, but not my work friends. There’s a huge generational divide here.

How can I politely bow out of this without burning a bridge? My weekends are precious to me and I also want to set a clearer boundary that I do not want or expect coworker involvement in my wedding or wedding planning. These coworkers are all my peers, not managers.

You can get out of this — just do it quickly before the planning goes any further! You can say, “It’s so kind of you to offer to do this, and I’m really grateful. My weekends are bananas right now, so doing it on a Saturday won’t work — would you be up for doing it during lunch one workday instead?”

If you don’t want to offer up that alternative, you could instead say, “It’s kind of you to offer to do this! But I think I’d rather not have a work shower — the rest of my life is so full of wedding stuff right now that’s it’s a relief to keep work more of a wedding-free zone. Still, though, it was so lovely of you to think of it — thank you for making the offer!”

– 2019

4. Company won’t hire me because I live in California

I applied for an online tutoring position for which I am well qualified. I was told that they are not hiring anyone from California due to having to make them employees per a new law in effect here, AB5, which limited companies’ ability to classify workers as independent contractors.

I make good money, have to maintain a home office and its technical equipment, and have no need of the employee protections. When I apply for a position, can I give a different address so they can treat me as someone living in a different state? It is an online position so where I live does not matter.

Where you live does matter, because the company will be subject to the employment laws in that state. If California law says they’d need to make you an employee rather than a contractor, they can’t violate the law just because you don’t care if they follow it or not! They’d be subject to penalties regardless. You can’t just opt out of the law.

Lying about what state you’re in would be fraudulent (are you going to give them a different address for your tax forms too?) and put them at risk — and would be an unethical thing to do to a company that’s trying to follow the law.

– 2020

The post asking junior staff to speak for their generation, I don’t want a bridal shower, and more appeared first on Ask a Manager.

https://www.askamanager.org/2026/06/asking-junior-staff-to-speak-for-their-generation-i-dont-want-a-bridal-shower-and-more.html

https://www.askamanager.org/?p=33634

Posted by Ask a Manager

https://www.askamanager.org/2026/06/updates-the-chatgpt-mansplainer-protecting-interns-from-drama-and-more.html

https://www.askamanager.org/?p=38507

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

1. My coworker mansplains via ChatGPT

Ultimately, for several reasons, I left the role. Though perhaps in hindsight, this should have been a signal that they weren’t the right fit.

The ChatGPT guy did get more obnoxious, at one point even suggesting we rewrite our entire codebase in another programming language using ChatGPT. Alison, this guy didn’t know how to write code at all and just assumed it would go fine. We’d literally be on Zoom together and I’d ask him something and watch him type it into ChatGPT. He just seemed to stop thinking for himself as time wore on.

Beyond that, there was some ugly corporate restructuring where I was given a title demotion and extra work but no extra pay, and the small amount of travel I had agreed to ended up being a large amount of travel. Corporate growing pains kind of stuff — it was a very small company that was trying to sort itself out and I just was caught in the middle.

So I left, and took a role more in line with my experience for a lot more money. Last I checked, they were hiring my replacement under the old title but less pay, and I wish them luck with that!

The new job unfortunately just handed us an AI usage mandate I’m not happy about and I think the vibe coding here is a bit off the charts too. But at least I feel like my experience and input and questions are valued and answered appropriately.

I don’t know if this will be a long-term role but it makes a difference to at least feel respected. I keep my tech skills sharp with projects outside my job, and I wait eagerly for the days where we can be more normal about LLM usage rather than shoving it in everything.

2. Protecting interns from office drama (#2 at the link)

Thanks so much for answering my question earlier this year and to the people who commented on it!

I had the conversation with both interns; both took it well and were grateful but I also think they (thankfully) were too inexperienced to grasp the full extent of the situation. No luck with Collins, though; in a related situation, she said she’d be grateful if I could be the one to talk to Trinity and I was able to steer her in the right way by framing the change of behavior I needed in a “please help me in this very tricky client situation by doing ABC.”

Robby and Langdon were fired a few weeks after I posted. There was more drama with clients, Robby was maneuvering hard against Collins in that time, but what ultimately did him in was that he had also made a number of decisions that didn’t make any sense on the business side. I have since found out that Robby managed to piss off pretty much every senior woman in the office by being condescending, mansplaining, and disrespectful to women specifically. Langdon was a goner when our CEO reached out to senior leadership of the client of a very big project and they gave not good, very bad feedback. I did share my concerns about Robby with our CEO as well (more about the business side of things) when the conversation pretty naturally came up when Robby managed to completely exasperate our generally very patient and even-keeled CMO.

I wish everything was hunky-dory and that we all rode off into the sunset but, probably to the surprise of no one, it was not so. I had high hopes for the new department head since I used to have a good relationship with her and she is very competent. But instead, Trinity took over Langdon’s big project, has become her new right-hand person, getting several direct reports from myself and others reassigned to her and continues to gossip, sometimes in a pretty nasty way. In fairness, I was asked if I wanted the big project, but I was already working weekends so I was relieved when I didn’t, but I didn’t count on that automatically resulting in, “Well, (MyName) isn’t that busy so she can take on this other thing” and “Trinity now walks on water, we all must protect Trinity at all costs” — when I was still having a higher workload than her.

The new department head has completely sidelined me, so long story short, I’m job searching but also think my job might be on the line, looking at the dearth of new projects in the pipeline; I would get a pretty hefty severance, so I’m trying to stay calm. On the bright side, I did manage to get Whitaker hired permanently (although he now reports to Trinity), and I’ve done pretty well detaching from all of the bigger leadership concerns and just focusing on my work and deliverables.

3. I keep getting pulled into work that’s not my job (#2 at the link)

I’m the technical writer from 2021 who kept getting assigned project management tasks on Project Coffeepot, with a project lead who dumped ALL of his overdue tasks on me. Well, as I mentioned in the comments, I did have to stick it out during Covid. Work slowed immensely, so I just let things ride and completed whatever task came my way.

Post-pandemic, the project lead brought in an entire team – eight people – to do what I was doing. (Guys, I’m not exaggerating the number. But the increase was in part because the project lead was an empire builder and planned to take over the department.) I was perfectly happy to turn over the management tasks, but then he gave them my technical documents as well. At this point, I was truly fed up. So I said, “Fine.” I went to my manager and said, “I need a new project.” (I’m part of a technical support pool and we get assigned to different projects.) Luckily, a new effort was starting and I got in on the ground floor. It’s been wonderful! I am doing technical writing (software requirements, software test docs – all kinds of fun things – yes, I’m a nerd and proud of it!), no project management, and getting plenty of recognition for the quality of my work. The team is great and I’ve been able to learn and grow my skills. I enjoy work every day.

As far as Project Coffeepot: two years later, the project lead came to me and stated that the new team had screwed up immensely and asked me to fix it. They were behind on all of the deliverables. I took immense pleasure in stating that I was tied up on Fabulous New Project and wasn’t available to help.

The project lead eventually transferred to another program. (Alas, his empire never came to be.) The new lead came in and within six months had erased the document backlog, got Project Coffeepot production back on schedule, and it’s now nearing completion.

4. Potential employer wants me to disclose any medical conditions, including migraines, depression, eczema, and more

I ended up politely withdrawing my candidacy the day you posted my letter. In addition to the health questionnaire, they wanted me to provide a recent blood workup for immunology, that I would have had to organize and pay for myself. Normally I would have been fine to do this, but again, this was all before receiving a formal job offer, for essentially an entry-level role that paid less than I wanted. Didn’t seem worth the hassle.

The hospital’s parent company ended up going into administration/receivership just a couple of months later. Apparently they’re $1.6 billion in debt and still looking for a buyer. Probably dodged a bullet.

The post updates: the ChatGPT mansplainer, protecting interns from drama, and more appeared first on Ask a Manager.

https://www.askamanager.org/2026/06/updates-the-chatgpt-mansplainer-protecting-interns-from-drama-and-more.html

https://www.askamanager.org/?p=38507

Posted by Ask a Manager

https://www.askamanager.org/2026/06/updates-boss-asked-about-my-fathers-life-expectancy-asking-about-ai-in-an-interview-and-more.html

https://www.askamanager.org/?p=38544

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

There will be more posts than usual this week, so keep checking back throughout the day.

1. My boss asked the life expectancy of my terminally ill father

My father died five weeks after you published my email (published on a day I happened to be traveling for work — so despite it all, I still managed in that time to fly to a client negotiation). It turned out I never had to deal much more with the intrusive questions and issues from the boss as I didn’t end up getting to take off as many times as I’d thought. Based on how he was doing, I had hoped and believed my dad would have had more time. A week before my father died, I took three days off and went home planning to mostly visit, but his condition significantly deteriorated right when I arrived so I ended up staying a week, in part out of pure 24/7 caretaking necessity. I took the next week off after he passed, as I was so burned out I wasn’t capable of working.

Back at work for a little over a week now and while no one gave me flack for being off, I am so discouraged at the overall response. Or lack of response really. I can count on one hand a few kind coworkers who reached out with thoughtful messages (none of them management level). The vast majority of people I work with haven’t offered condolences or any acknowledgement.* Nary a word from the “big” boss (who used to be my boss before his promotion). Yes, all these people were notified. One coworker today offered me his condolences at the end of a call I made to him, which felt like an afterthought on his part, and literally said, “I’m glad he’s at peace now.” I never talked to this person about my dad’s illness. Pretty sure Dad would rather be alive.

I don’t know if this is how most people are these days and my standards for etiquette are too high, or if I’m just unlucky in my coworkers and management. My practice is to always send condolences to anyone I work with (or interact with more than once in any context!), and privately and separately – not as an afterthought added to a business call or email. My dad’s job he retired from 10 years ago sent flowers to the gravesite. Several of my mom’s coworkers from her job she retired from seven years ago came to the service. And I get crickets from most of the people I work with right now. One could say I shouldn’t be hurt by self absorbed coworkers, but I’m struggling so much right now to be motivated to do my work. Needless to say, I am actively looking.

* To anyone who doesn’t because they are afraid of remind the person of their loss or don’t know what to say: (1) They haven’t forgotten their loss. But they may not want to be put on the spot during a business meeting and potentially become unexpectedly emotional in a professional setting. This is why you offer condolences privately. And (2) Don’t know what to say? It’s hard to go wrong with “I heard about [X] and want you to know I’m so sorry and am [thinking about][praying for] you. No need to respond but if you want to talk I’m here.” Copy, paste.

2. Asking about AI in an interview (#5 at the link)

I was the one who wrote in asking about a company’s AI use in an interview. You were very kind to say my wording was great, and I felt empowered going into the interview. The hiring manager’s response was, if I recall correctly, that the company wasn’t in the habit of using or embracing gen-AI at that time, but they weren’t opposed to AI tools for administrative tasks. She wasn’t put off by the question at all, which I feel fortunate about. I’m really delighted to say that I got that job, and I’ve been there ever since!

Obviously, AI use has only increased in the last few years, and the discourse around it has increased even more. In the last year, my company has issued statements and become a bit known in our industry for being vehemently anti-generative AI, while in the rest of the industry is aggressively adopting it.

This is a minor update to an unimportant question, but I do want to use this chance to say that if you are against generative AI but everyone around you is telling you “it’s here, just get used to it,” you really don’t have to. You’re far from the only one against it, and there are places that will refuse to use it in creative processes. It’s only inevitable if people allow it to be.

3. My coworker keeps insisting I must speak Spanish (#5 at the link)

I had a proper sit-down with the department head and had a talk about the situation and it stopped immediately.

4. My job is really flexible but it also sucks — is it time to go? (#2 at the link)

As it’s a whole year later, I wanted to provide an update!

I must have known subconsciously something was up — about a week after you posted your response, I got laid off, and I think it makes total sense. My the scope of my role didn’t make sense anymore, and I think they wanted someone local.

Some of the freedoms I enjoyed while working there, upon reflection, were probably mostly due to some deeply entrenched disorganization at that office. A few weeks after they laid me off, the new manager called me in a panic because no one could figure out how to submit the quarterly report I’d been in charge of. They paid me a consultation rate for the couple hours I spent on helping them, which I appreciated. Also, I had asked during my layoff call if they would send me a shipping label to send my laptop back. It wasn’t until a few weeks ago (!!!) that they reached out to figure out those logistics.

I am still in touch with my old managers who had left before I did, and it’s only after a ton of hindsight that I was able to see how dysfunctional that old office was. Getting laid off was honestly a relief after all that back and forth, and it allowed me to stay on unemployment while I looked for a new role. It took me the full six months to find something, so I’m doubly glad for it (as opposed to applying out while white-knuckling it at the old place for those six months).

I got hired by another organization back in September, and I’m much happier here. It pays just a bit more, fits closer to my skillset, and very notably, is still pretty flexible! I am completely WFH, can run an errand or two during the day so long as I let the team know, and I don’t even have Teams or Outlook on my phone. I’m also not the only person in my role, the company itself is much larger with more safeguards and clearer lines of report.

So: a happy ending for all! Those six months of unemployment were tough, but I’d take it over still working at my “unicorn” job.

5. The yoga studio where I teach hasn’t been paying me on time (#4 at the link)

I’m the yoga teacher who didn’t get paid for 21 classes. The comments were great, specifically one that said the gym owners wouldn’t let someone take classes without paying.

It turns out the owner did have a medical issue and was out for a month or so, but the other manager didn’t step in to pay (though that was the person that managed the yoga teachers and was my contact). I did say that I needed to be paid or I wouldn’t teach moving forward. They ended up paying me for all my classes and I requested to be put on their payroll. All the trainers are on payroll, but the yoga teachers were not. It turned out the other yoga teacher hadn’t been paid either and she thanked me for speaking up.

That being said, all is well. Not sure how long I’ll stay there, but I’m okay so long as I’m getting paid! Thank you for the great advice!

The post updates: boss asked about my father’s life expectancy, asking about AI in an interview, and more appeared first on Ask a Manager.

https://www.askamanager.org/2026/06/updates-boss-asked-about-my-fathers-life-expectancy-asking-about-ai-in-an-interview-and-more.html

https://www.askamanager.org/?p=38544

Posted by Ask a Manager

https://www.askamanager.org/2026/06/updates-the-married-couple-the-fitness-tracking-device-and-more.html

https://www.askamanager.org/?p=38499

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past. Here are five updates from past letter-writers.

There will be more posts than usual this week, so keep checking back throughout the day.

1. I manage a married couple, and it’s causing problems

I set up meetings with each of them, back to back, and basically had the same conversation with each of them. I scheduled it that way because I wanted each of them to be coming into the meeting “fresh” and not responding based on what I had said to their spouse. This worked well. I had good conversations with both where I made it clear that they cannot fight each other’s battles at work or speak for each other otherwise and that if they aren’t asking for what they need, it’s not reasonable to put that resentment on me or others. With both of them, I had good chats, especially about that last part, and how we could work to prevent that from building up in the future. In one case, that resulted in more frequent one-on-one meetings with me and that person. For the other, I think giving them permission to focus on their own job responsibilities and treat their spouse like a colleague at work was most of what they needed.

I won’t say that this 100% solved everything. One spouse struggled with the resentment for a while longer, and we had a series of conversations about it through the fall, one of which got pretty heated between us, but after I apologized for snapping at them and we had a chance to take some space and come back to discuss again, we ended up in a better spot. Reading between the lines, I think they’ve been struggling with some things in their personal life that made the pattern that led to the resentment at work especially hard to let go of, but I think they are getting some support to work on that outside of work. Things are much better now and they have been much better about asking for what they need to me and the broader staff.

2. My boss wants me to buy a fitness tracking device

I said I wouldn’t buy the tracking device for the last time and they actually let go. Then on an offsite, my employees asked that we all buy it and have a group competition. Since it came for the employees, I adopted the idea and we paid for their devices.

Some insights from this story:
1. I really believe that me standing up against the peer pressure as a C-level set an example for my employees.
2. My founders and I are close and it didn’t affect our relationship at all. I believe their intentions were pure albeit maybe unprofessional ?
3. You should start ask a manager podcast.

There was an Ask a Manager podcast, but I ended it in 2019; it was a lot of fun, but also a ton of work. But all the old episodes are here.

3. Is it okay to hang target practice sheets up at work? (first update; second update)

I wrote in quite a while ago because somebody in my office had gun target practice sheets hanging in their cubicle and it made me very uncomfortable.

Since I wrote in, I left that job (for a variety of unrelated reasons), moved to a different state, and a couple years ago changed careers from a series of boring, super-corporate desk jobs to a public sector job in the court system. Through this work, I have been exposed to way more detailed information about gun violence in my community and state. Thinking back on my letter, what strikes me is how little of an idea I had then of just how many people own/carry guns in the U.S. It’s something I would never even consider for myself, and knowing now how prevalent it is while also seeing the consequences on a daily basis at work is very unsettling.

I remember getting roasted in the comments for having an “irrational” fear of guns but with every passing year, fearing guns becomes increasingly more rational. It’s scary out there!

4. We’re pressured to attend after-hours social events at our own expense (#4 at the link)

I did not take the approach of gathering a group of folks together to advocate, more because of complexities of our org structure I didn’t include in my email. I gave one additional piece of feedback to leaders and then established a personal/professional boundary. Over the last few months, our financial stability has been in question and therefore I pointed out to leadership that it would be aligned with our mission and values not to ask staff to personally fund work-related activities when their future paychecks weren’t certain. After that, I established the boundary that I would only attend events that happened during the work day or where the organization was going to cover costs I incurred. I have attended zero events since.

And now, I am joining another organization where I will be part of the decision-making leadership and hope that my future team members do not have to reach out to you about me!

5. Should I tell my interviewer I like that the city is LGBTQ-friendly? (#4 at the link)

I recently emailed about the pitfalls and subtleties of interviewing while trans, and I just landed a new job, having interviewed as my new name and gender through the whole process! There are still some tricky things when it comes to paperwork, insurance, and legal signatures, but I’ve been impressed at my new employer handing things sensitively and trying to get it right with me. Thanks for your advice in that answer and in general, I had a few pieces of AAM advice at the front of my mind as I interviewed!

The post updates: the married couple, the fitness tracking device, and more appeared first on Ask a Manager.

https://www.askamanager.org/2026/06/updates-the-married-couple-the-fitness-tracking-device-and-more.html

https://www.askamanager.org/?p=38499

Posted by Ask a Manager

https://www.askamanager.org/2026/06/update-my-job-wants-me-to-be-both-an-employee-and-a-contractor.html

https://www.askamanager.org/?p=38140

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past.

There will be more posts than usual this week, so keep checking back throughout the day.

Remember the letter-writer whose job wanted them to be both an employee and a contractor? Here’s the update.

I was planning on having an update much sooner, but then the situation just continued to snowball. But I finally have a mostly-happy ending to share!

I did end up signing the contract, about a week after I had originally sent my letter. I hadn’t gotten Alison’s advice back yet, but I think I already knew what she and the commenters affirmed — it was almost certainly a bad idea. Unfortunately, I didn’t feel like I could turn down the contract without really jeopardizing my relationship with my job (and particularly with our very hot-and-cold CEO). I did get them to agree that I would be paid biweekly though — so my contractor payment would be added as a bonus to my hourly paycheck — instead of as an end-of-year bonus.

That probably would have been the end of an unsatisfying story, except that later that week, someone made a post online accusing our CEO of a major personal scandal. (For anonymity’s sake, I won’t say what kind, but if you just think of the most horrible thing a person could be accused of … yeah.)

After a week of lots of board meetings and uncertainty, our new C-Suite came forward to announce that we would not be moving forward with the planned project (which was designed by our old CEO). Instead, we would be creating/executing a new from-scratch concept — with about five weeks before the project launch. (We had been working on the old project for several months, and had already spent a lot of our budget on it.) I got brought back on in the same hourly + contract fashion, but with the scale of the project very considerably changed. Everything was moving so quickly that there was no renegotiating or discussions of how things would change — we all jumped into working on this new project feet-first.

It was an incredibly hectic month of working 70-80 hours a week (with half of it as an “hourly employee” and half of it as a “contractor”… which is to say, working at my regular rate with no overtime), but it was also one of the most exciting moments in my career. After working for someone who was so ego-focused and unwilling to entertain any opinions that were not his, it was great to be on a team where everything happened so collaboratively. Work-life balance went out the window, but at least it was working towards something I was actually proud to put my name on. At one point I remember telling my fiance (who was such an incredible rock during this whole thing), “I’m really having a great time being taken advantage of.”

This was going to be the end of my update — “hooray, my terrible CEO has left and I’ve reconnected with the passion I have for this work, even if it does suck to be paid so poorly for it.”

But!

After the project ended and we all took some time to decompress, we had a retrospective on the project, and I asked my skip-level boss for a one on one. (I re-read Alison’s advice and the comments section on my commute to that meeting for encouragement — thank you all!)

I had two goals for the meeting: (1) to make sure they knew that I knew that this setup wasn’t legal, and (2) to make it clear that I wasn’t willing to enter that kind of arrangement again. (In a ideal world, should I also have gone in looking for money? Yes. But I also knew that the company had taken a serious financial hit in dealing with ex-CEO’s exit, and it didn’t feel like the battle worth fighting.)

After spending a fair portion of the meeting being sympathetic but sticking to her position (“I’m sorry that you feel undervalued, but there was nothing illegal with what we did”), my grandboss agreed to revisit the issue with our CFO and schedule a follow-up.

Thus followed a very stressful two-week wait, including a request from the CFO for the full combined time logs from those months. Boss and Grandboss also put some new protocols in place for my role (lots of conversations about “having better work-life balance” that mostly equated to “no working from home, less flexible scheduling, and more strict timekeeping”). I suspect this is largely because they realized how little oversight my job historically had — my boss would be very happy to just focus on the non-management part of his job and let us manage our own work and schedules. Now that my timesheets were being called into question, that was no longer going to fly.

Finally, close to two months after the original project had wrapped up, my grandboss and the CFO scheduled a meeting. The conversation started out with ‘we want to pay you legally and fairly” (hooray!), but also “we had no idea how much you were actually working during these months” (a little difficult to believe, since I was here all the time, as were they) and “we made you a contractor so you had more flexibility to self-manage without worrying about hourly limits.” This last point was in part fair — that flexibility was pretty essential with how quickly everything was moving — but it’s not like I could have reorganized my time to somehow fit all the work that had to be done in a way that wouldn’t have led to overtime. It wasn’t until they kept harping on that last point and going over a few weird specifics with my time logs that I realized that they were misinterpreting California labor law…. and that they had come to the conclusion that they owed me significantly more money than they actually did (by an order of at least 20 times, if not more).

We went and googled some laws together, they realized that I was not about to suddenly become the most well-paid employee at the company, and suddenly the conversation became much less tense!

All in all, it’s a pretty happy ending. This place still has its fair share of disfunction, but it’s also becoming pretty clear that new leadership does really care about the company culture of people working here and are open to hearing suggestions and change. I got a nice unexpected “bonus” from the overtime pay I should have been paid, were everything done above board. And as much as not having work-from-home and flexible scheduling felt like a punishment at first, I am learning to enjoy putting down work when I’m not in the building and letting messages and emails sit until I’m back. It’s not the place I want to work forever (and in fact, I just started gearing up to start my job search again), but for the work I’m doing right now, I’m pretty happy with how everything ended up.

Alison, thank you so much for the amazing resource that Ask a Manager has become. I’ve read this blog as fun reading for years, and I hadn’t realized quite how much useful information I had absorbed until I was going through all of this. As a young professional, having a sense of what is normal vs. dysfunctional vs. illegal has been hugely helpful in protecting myself (not to mention then being able to assert those boundaries while still maintaining positive professional relationships!). You and the Ask a Manager community are incredible and I’m very grateful for your help in how this all got resolved — I’m not sure I would have had the confidence or knowledge to stand up for myself without you all.

The post update: my job wants me to be both an employee and a contractor appeared first on Ask a Manager.

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Posted by Ask a Manager

https://www.askamanager.org/2026/06/lets-discuss-cases-of-extreme-obstinance-at-work.html

https://www.askamanager.org/?p=38661

Let’s discuss strange cases of extreme obstinance at work — times when someone just dug in their heels and refused to do a thing, and what happened as a result. Here are some doozies we’ve heard about in the past:

• I had a couple coworkers pitch a huge fit when my employer updated the dress code. What did they change? No pajamas. Not even kidding. This was at a call center and the dress code was VERY relaxed, but we had people literally coming to work in their PJs or similar nightclothes. The best part was some of the worst offenders went on to harangue management over it, since “it was never a problem before” and “we’re not face to face with customers so why does it matter.” People would show up in defiance in PJs and argue when they were told to go home and change.

• Nary a month goes by that I don’t think of a guy at my customer-facing work-study job in college. We started at the same time, and about four months in we switched the main software program we used (moving from a Unix-based system to something a touch more modern). He just … decided that he didn’t want to learn the new system and wasn’t gonna, so he sat in the back and read his Bible for his entire shift, every shift. He wouldn’t even process voicemails because those voicemails needed to be logged in the new software program.

I was promoted to student manager not long after the software switch, and after a couple weeks of dealing with this guy’s obstinance, I complained so much that my managers stopped scheduling him with me, and they didn’t renew his position the following year. But he got to spend four months doing absolutely nothing and getting paid for it.

• When I worked at in the office of a warehouse, we would get a freezer full of ice cream bars in the summer. It actually had to be addressed that workers MUST STOP taking entire boxes home with them. One coworker took such offense to this that he would made it his mission to eat as much ice cream as possible while on site. I watched him eat seven of them during a thirty minute lunch break. He would proudly boast about how he’d make himself sick on free food just to make sure he got his “fair share.”

• When I worked at a Scout camp, we would usually get two shirts each summer specific to the year: a polo shirt in that summer’s color, and a t-shirt listing what area of the camp you worked in. For years we wore the polo shirts on Mondays and the area shirts on Wednesdays, when families came to visit. Then one year management decided we should switch that, so campers could see who worked where at the start of the week and we’d all look nice and fancy when Mom and Dad showed up.

There was a minor uprising. Yelling arguments. Flat refusal to cooperate. We had staff for YEARS after the change who would wear the wrong shirt and say “oh — you didn’t tell me we were doing it different this week from how we’ve always done it.” We had staff members going so far as to carry two shirts with them all day Monday and Wednesday so they could put on the correct shirt when management was around, then change back to the other shirt when nobody was looking. Some of the worst offenders were our old retired guys (who are like gold, it’s hard to find adults to work at summer camp, so they weren’t disciplined over minor shirt disobedience) and carried the torch for their preferred shirt rotation for a literal decade after the change.

Please share your own stories of extreme obstinance in the comments!

The post let’s discuss cases of extreme obstinance at work appeared first on Ask a Manager.

https://www.askamanager.org/2026/06/lets-discuss-cases-of-extreme-obstinance-at-work.html

https://www.askamanager.org/?p=38661