the CEO caught cheating on Jumbotron, my employees don’t want to earn raises, and more

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

1. The CEO and head of HR who got caught cheating on a Jumbotron

I am dying to get your thoughts on this story that is going mega viral about a CEO and head of HR who were busted on Jumbotron at a Coldplay concert.

Apparently the other woman on the Jumbotron hiding her face and laughing is another HR professional at Astronomer. This has wayyy blown up. I would love to get your take on this!

It’s very bad. It’s already a huge problem for a married CEO to have an affair with his employee (who’s also married, although it would be a problem either way), but when the affair partner happens to be the head of HR?! How could anyone working there ever trust that the company would handle reports of sexual harassment appropriately? (Particularly if said complaints are against the CEO who’s having an affair with the head of HR…)

Moreover, the other woman shown in the video next to them is apparently the head of HR’s second-in-command, who she just promoted to that job after working with her at several other companies before this. Having another HR higher-up present is a sign of further mess, as she would have an obligation to report the relationship. Her presence and obvious awareness of their affair raises additional questions about conflict of interest in her performance of her job, too.

Oh, and the person the CEO is having the affair with is the only woman on their 12-person leadership team.

So, yeah, a mess, and none of them can credibly remain at the company.

2. My employees don’t want to earn raises by increasing their skills

I own a coffee shop in a rapidly growing town and have had success since starting in 2020. Prior to 2024 we had fairly high turnover, 20% per year. We only have 10-12 employees, myself included. At the beginning of 2024, we made the decision to raise pay significantly, start offering PTO, health, vision, and dental, and we have not lost a single person (unexpectedly) since!

To increase skills, I offer all employees raises if they can pass skills-based tests. If they pass all three tests, they get an almost 10% raise. Yet very few people have taken the test, and the overwhelming feedback is that “test anxiety” is too bad. The team’s attitude has become very negative and gossipy about me, as I am the only one who asks about their work and tries to instruct them on how they can improve.

I’m to the point where I feel like the best step would be to make the skills tests mandatory (after 18 months of employment) and those who would rather gossip than take relevant advice will be filtered out. However, this could very well lead to losing a lot of people which would bring back the high turnover issues we had before. What should I do?

Separate the test issue from the negativity and gossip, because they’re two different things. It only makes sense to make the test mandatory if you genuinely need people to have mastered those skills in order to stay in their jobs; if you don’t, then don’t require it. Requirements should line up with what you actually need.

Is the negativity and gossip all coming from people being annoyed that you keep coaching them on their work? And is the coaching being framed as to help them pass the test? It’s of course reasonable for managers to coach people on their work, and if you employees are bristling at that, then is it something about the way you’re doing it? Are you micromanaging? Picking the wrong time when they’re busy with something else? Being overly critical or having unrealistic standards? I don’t know, but that’s where I’d start looking, and you should ask people directly for their perspectives about that. If it’s not the way you’re coaching them and they just object to the idea of needing to get better at their jobs, then there’s a pretty serious problem with the people you’ve hired and are choosing to retain (and zero turnover is not always the right goal; sometimes you need some turnover). But start by finding out what exactly people are bothered by.

3. How can I tell colleagues their AI-generated writing is making my work harder?

I am a communications professional who does a lot of writing, mostly speeches and written messages for the president of our organization. I’m being promoted to a role that’s more focused on strategy, so some of the writing needs to come off my plate. I’ve worked with my supervisor to delegate some assignments to others across the organization. Our fundraising communications lead, for example, will write the fundraising message from the president. My problem is that writing keeps coming back to me having clearly been written by AI. I think it’s partly because the person submitting it thinks it’s good enough (it’s not), but mostly because they know it will go through me to put it into the president’s voice before it actually goes to the president — so they know I will just rewrite it if I have to.

It’s obvious that most of these deliverables are a slight rephrasing of something I’ve written in the past, with a few prompts to fit the topic of the new message, and very little editing. The classic signs of AI are all there, like overuse of buzzwords and certain sentence structures. Look, I use AI as a writing tool too, but it’s just that — a tool that can help me finesse or wordsmith, not something I ever use verbatim. Our president has a very high standard for anything with her signature attached. It has to sound like it is truly in her voice and sends an authentic message.

How can I help my colleagues understand that they need to do more than have ChatGPT spit out a draft? I’d guess the answer is to just give them really clear feedback on how the draft needs to be improved (whether or not it was AI-derived), and train them more thoroughly on presidential voice and tone. But the age of AI is making this problem a lot more rampant than it was before. I want to tell them that it’s really obvious this is an AI message, but I also don’t want to sound hypocritical because it is a part of my toolkit too. I also don’t manage any of these staff, they’re just colleagues across the org, sometimes lower than me in hierarchy but oftentimes at the same level. I can tell they use AI all the time in the work they produce in their own divisions, but when it comes from the president, the layers of approval are different and I need them to raise the standard.

First, training people to write in a specific person’s voice is hard. Unless these are professional writers, it’s a skill that the majority of people don’t have, and probably won’t develop in the time you have available to train them. So it might not be realistic to expect them to turn in copy that’s already in the president’s voice. But it’s definitely realistic to expect them to not give you slop, so focus there.

Also, you’re right that it makes sense to give really clear feedback on the specific ways the draft needs to be improved. But it’s also fine to say something like, “Can I ask whether you used AI as part of this? Some of it reading as AI to me, and we obviously never want our work to sound that way. So if that’s part of your process, it’s helpful for me to know so we can jointly figure out what will help get these closer to what we need.” (That’s more nuanced than “never use AI for these,” although that might ultimately be what you end up telling them. Approaching it this way also might make them more willing to be open about if it they did use it.)

4. Can I leave my master’s off my resume?

For reasons that are obvious, I am considering leaving the federal workforce. Jobs I’m considering require a bachelors degree and a certain number of years experience.

I have a master’s degree. Would it be bad form to leave the master’s off of job applications and resumes? Would employers be upset if they found out afterwards that I had a master’s and did not reveal this during the application process/interview? Could it lead to an adverse action if they did find out?

You can leave the master’s off your resume if you think it will make you a more competitive candidate. A resume is a marketing document designed to present your strengths, not an exhaustive listing of everything you’ve ever done. (The exception to this is if you’re filling out an application that explicitly asks for the highest level of education you’ve completed.)

That said, I wouldn’t automatically assume it will help to leave it off. In some cases it might — like if the master’s is in a totally different field and might raise questions about how committed you really are to the jobs you’re applying for now (which is BS for many reasons, but is a thing that happens) or if it’s likely to make them think they can’t afford you. But in many jobs it would be a plus or a neutral.

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