CEO is furious about my joke, boss keeps saying he loves me, and more — Ask a Manager

It’s “where are you now?” month at Ask a Manager, and all December 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 CEO is furious about a joke I made

Thanks for publishing my letter. I wasn’t able to respond to comments that day, but I read all of them. Some commenters speculated that the CEO initially thought I was serious and was alarmed; he definitely knew I was joking from the get-go and did not like being the butt of the joke. (Most of his jokes are intended to keep the subject a little off balance, but that is supposed to be a one way street).

A coworker later suggested that since another PM was in fact struggling with keeping up with her project, which was causing major problems, the CEO might have thought I was referencing her struggles and it hit a little too close to home. I wasn’t, but it would make his reaction a little more explicable.

I have also since learned from other folks in the industry that he has often responded disproportionately angrily to things you wouldn’t expect. Overall the joke probably helped my reputation amongst my coworkers since most of them disliked the CEO, so they found the situation amusing because it made him look thin-skinned and a little foolish.

I didn’t see the CEO for a while after this incident and while he clearly remembered the encounter, he didn’t mention it and congratulated me on how the project went. The division VP who’d reprimanded me started acting more abrasively towards me, but he was treating everyone the same way so I didn’t take it personally. My boss did mention the incident in my yearly review as a word of warning, although he clearly thought the CEO’s reaction was ridiculous.

Shortly after many people I worked with left the company, and I did as well. I ended up finding a much better-paying job, remote, with really good (and pleasant) bosses who have no issues with humor. So far I’ve been very happy here.

I’ve kept up with some folks from Old Job and it seems many are thinking of leaving. I would never, ever work for either CEO or VP again if I can possibly help it, so it’s not likely I’ll ever run into these folks again (but it’s a small industry so who knows!). Since things turned out okay, I don’t regret making that joke, although in a vacuum I wouldn’t do it again. The whole situation really opened my eyes to the importance of corporate politics; somehow I’d mostly avoided it before this but the amount of gossip and nepotism at that job was incredible. Overall, I’m happy with the way things turned out.

2. My boss keeps telling me he loves me

As many of the commenters guessed, my boss does come from a place where “I love you” or “love you” is a common way to end a conversation, although he doesn’t seem to do it with anyone else. He’s pretty much stopped, presumably due to me giving a weird look every time he said it. Our working relationship continues to be strong! He promoted me to the senior leadership team and I continue to be able to bring up challenging topics with him that others couldn’t. He does suffer a bit from lack of boundaries — just recently he mentioned to me that he had a prostate exam, but it was fine to tell me because “they do blood tests now, not the finger up the butt. Well, they still stick the finger up the butt later, but that’s after the blood test I think, they just don’t open with the finger in the butt any more” — but that’s just who he is. And frankly, it’s refreshing to work for a boss whose “finger up the butt” stories are medical. That’s progress for my industry.

– still don’t love him, but I like him just fine

3. Can I take off a full week when no one can cover for me? (#4 at the link)

Your advice was indeed very helpful and reassuring.

Here’s my update: The company hasn’t changed much, but I have:

· I’ve required that others provide information I need to fulfill their product needs on a timely basis, or it doesn’t get done.

· I’ve made it clear that because of my broad background, I can do almost anything, but not everything. We can do “A,B,C” but not “D,E.F.” If I’m clear and consistent, I don’t get heavy pushback. This has reduced workload.

· I insisted I be allowed to hire freelancers who can take on much of my back-office work, making it easier to get ahead before vacations.

Those three items above have made real vacations possible for me and for the company. I also made a logical case for raises. They weren’t large, but my staff and I got something, which improved morale here.

4. Our director left while my coworker was on vacation (#3 at the link)

The advice was spot on.

My update is that the coworker was fine learning about the news in a casual way when she got back. Unfortunately, I was not hired for the permanent position. There were a lot of red flags in the hiring process. The interview was scheduled at the last minute (on a Thursday when she pledged to announce who was hired on a Friday). The executive director also told me, verbatim, after my interview, “Well, you know I want to hired you, but I have to interview Jane to make sure she doesn’t get mad.” She took Jane on a 15-minute coffee interview the next day. She gave Jane the job. For reference, Jane has less experience, training, and credentials than me. I was given a smaller promotion but that wasn’t enough to balance out that Jane and my ED cut my most interesting tasks, removed me from all important conversations, and undermined me at every turn. After a long and frustrating summer, I got a new job in a related industry for a little less money. I am thrilled with the new job and excited for a fresh start.

The most interesting part about my new job is that I’m in a “project engineer” role (my smaller promotion was to “senior engineer”) so technically a step down, but the levels at my new organization are massively different. At my old org, my new director and ED were very young and inexperienced. The new job, people have way more experience. While that likely means I won’t make my way up to senior engineer in the near future as I hoped, I am actually a lot happier to be learning and growing with people who have something to offer in terms of professional growth!