It’s a special “where are you now?” season at Ask a Manager, featuring updates from people who had their letters answered in the past. Here are five updates from past letter-writers.
1. Copywriter Is Using AI to Produce Bad Work
The long story short is that I didn’t do much, but my thinking has definitely shifted towards acceptance.
I left my boss’s AI use alone. That’s her call to make, not mine. It falls into the category of “your boss sucks and isn’t going to change.” It’s gotten better too — she doesn’t copy/paste long swathes of randomly bolded and emojified text anymore. I’m sure she’s still using it, but it’s more subtle, which I appreciate.
I decided if my report’s AI-generated text became an obvious element on a high-profile project, I would address it directly, but that never came up. He’d been using it on assignments that were essentially busywork. And honestly, I can’t really fault him for finding an efficient way to produce tedious work that exists mainly to boost SEO … let the robots talk to the robots, I say. Shortly after this, I was able to get him on a meaty long-term campaign that’s taking up most of his time and plays well to his strengths. The writing and content direction he’s producing for that project is engaging, and I haven’t asked about AI involvement. It doesn’t read like generated text, which is good enough for me.
I’ve also had a change of heart about AI in the workplace in general. No, I don’t love it and I still don’t really use it, but I still have a while before retirement is likely. I need to figure out how to adapt if I want to stay relevant. I make plenty of ethical compromises in other aspects of my life; this is just another one. In service of this, I joined an AI steering committee in my workplace, partly to learn how other teams are using it and partly to try and quietly influence company policy — how data is stored and managed, what guardrails are in place to prevent our bots going rogue, that kind of thing. I won’t be the final decision-maker on anything, but I can at least raise the questions.
All in all, I feel positive — I feel less like I’m battering my fists against a closed door and more like a pragmatic person who’s making the best decision they can in a changing landscape. I really believe that much of life is learning how to adapt when things don’t go the way I want them to, and this is just another example of that. So instead of being irritated and inactive, I am doing what I can do within the context that I’m in. Being intentional in my thinking about what actions I am taking and why has helped a lot.
2. Does HR-Mandated Manager Training Ever Fix Bad Bosses?
When I last wrote, a toxic director (Niccolo) had driven me and many others out of the company. His many bad behaviors led to him being assigned training by HR. My question was whether such training is ever effective.
For Niccolo, the main effect it seems to have had is causing him to distance himself from the rank-and-file. He canceled all 1:1s with anyone not directly under him and would only interact with even senior staff members through intermediaries.
Now for the drama. Beloved CEO Giulio stepped down, and a new CEO (Rinaldo) came on board to replace him. Rinaldo was also a bit problematic, but in different ways from Niccolo. In fact, Rinaldo strongly disliked Niccolo and apparently tried to get rid of him.
Remember that I said Niccolo had friends in high places? That would be his C-level buddy Lorenzo. Lorenzo was not only a chief officer but also was on the board. A couple of months ago the board fired Rinaldo and replaced him with Lorenzo, who now holds two C-level titles. I don’t think Rinaldo trying to get rid of Niccolo is the sole reason he was fired, or even the primary reason — Rinaldo was very unpopular, was a major and unapologetic culture clash with the rest of the company, and also engaged in some financial malfeasance that the company is still trying to untangle, though I don’t think that was discovered until after he was already out. But it definitely seems as though Niccolo is well and truly untouchable.
Meanwhile, Niccolo has been promoted twice in less than a year. He’s now senior VP over his entire organization. There are apparently some whispers that Lorenzo is going to appoint him the new CEO. Absolutely wild considering that he started at the company as a line manager.
I’m quite happy I got out when I did, as the company is losing multiple highly skilled and tenured employees every month and the job market is … not ideal. Being one of the first rats to flee a sinking ship gave me my choice of driftwood to latch onto (if you will permit me to stretch that metaphor so far).
As for the question I asked: reporting Niccolo and HR assigning him manager training only made things worse and exposed who his enemies were. He carefully and methodically picked each one off, never exposing his hand to the point where he could be accused of retaliation. He assigned one of his strongest opponents a project with a timeline so aggressive he would almost certainly fail, and that employee left the company — the project was then quietly shelved after he left, never to be spoken of again, despite being “critical to the company’s success” beforehand. This is a highly unsatisfactory update as the bad guys win, but it’s what happened.
3. Should I Clarify My Boss’s Email to Her Boss and Grandboss?
I ended up not forwarding the email to my grandbosses, due to just wanting to move on and feeling like too much time had passed on the issue. At this point, I don’t think my manager’s supervisors will do anything to address her performance; when I brought up my ongoing frustration with one of them, she turned it around and strongly encouraged me — to the point of telling me — to go to EAP to get help with my work frustration, so that I could keep my personal therapy sessions focused on my personal life issues rather than work issues.
However, there have been two small positive steps: my branch has closed for renovations, so I’m not seeing my manager day-in and day-out. And my library system now has a chief people officer in HR, so I had a confidential conversation with her about the communication issues I’ve seen with my boss, and how her supervisors are not able to address them. That was about a month ago, so we’ll see if anything happens. My branch is going to be closed for the rest of the year most likely, so at least I have a break for the rest of 2026.
4. Timing My Resignation With a Week Off and a Company Retreat
Thanks so much for running my letter! It ended up being a non-issue because the person who had planned the past several retreats had left the company earlier in the year, so it was planned by a different person and took a very different format. The day was more focused on reconnecting with the organization’s mission — activities like reading a news article related to the work we do and then discussing it in groups — general team-building games, and sharing big-picture goals for the coming year at a department-by-department level, not individual role or professional development goals. So fortunately, there wasn’t any of the particular flavor of awkwardness I’d been dreading.
I ended up giving my notice two days after the retreat, and while my boss was disappointed to see me go, he wished me well and didn’t seem to find the timing odd at all. I successfully launched my business in the fall as planned, and while it’s had its ups and downs, it’s been a great experience.
5. Can I Ask My Old Job to Take My Name Off Their Website?
I did end up emailing my former manager and asking her to remove me from the website. She blamed the slow IT people, and nothing happened for a while. Finally, months later, the website was updated and a lot of things changed. I found out my former manager had been fired for essentially not doing her job for a long time, and her daughter quit in sympathy. I found this both delightful and validating. I’m happy at my new job, so it’s a good ending all around. Thank you, as always, for the advice!
