I think my boss is ChatGPT

A reader writes:

I started a new executive-level position with a young-ish start-up a few months ago. My boss had always seemed distracted in meetings or like he wasn’t fully listening. He has an aversion to synchronous meetings and exhibited some bizarre behavior early on when asked a clarifying question about a concept he had shared with the company (leaving a meeting abruptly and not returning).

This behavior baffled me until I typed a few prompts into ChatGPT and realized that much of what he communicates asynchronously is almost identical to the output. Then I noticed it everywhere — huge project plans that pop up out of nowhere, strange shifts in business strategy that are communicated oddly and not elaborated on further when asked … he’s … using ChatGPT for everything. He’s not being transparent about it.

This leader is very young in his career — this is his first job out of college. I can see that he’s under a lot of pressure and doesn’t feel comfortable not knowing everything. I’m much more senior in my career, and I feel like I’m doing him a disservice if I don’t share with him that what’s happening is noticeable. What do I do with this knowledge? Others are also noticing and mocking him behind his back. Historically, he has not taken feedback well.

Do I try to coach him? Run? Is this standard practice, and I’m out of date? Is this the “you won’t always have a calculator in your pocket” of our time?

Should I pose this to ChatGPT and see what happens?

The key in your letter is this: “Historically, he has not taken feedback well.”

If that weren’t the case — if he had shown humility and an interest in receiving feedback, or at least no pattern of shooting the messenger — this would still be a difficult conversation to have! In that situation, though, there might be room to attempt a conversation, not necessarily accusing him of relying on ChatGPT for all his communications but raising the issues the ChatGPT usage is causing. After all, if this were happening prior to ChatGPT’s existence, the unclear communication, bad planning, strange strategy shifts, and so forth would still be problems, and you could focus on those outcomes without speculating on the cause. If you had good rapport and a trusting relationship, you might be able to name it more directly, but that’s very relationship-dependent.

However, your boss has already shown himself not to take feedback well, so that makes it a no-go. It’s kind that you want to help him and you’re right that speaking up could be doing him a service — but he’s already shown he’s not likely to handle the conversation well. Given the power dynamic, you’re not under any obligation to make things harder for yourself professionally or cause tension just because he could benefit from it!. To the contrary, if your boss wants to benefit from feedback from the people he manages, he needs to create conditions where people know they’ll be safe providing it. He’s not done that; he’s done the opposite.

You’re not responsible for saving him from himself, and especially not when there’s a decent chance it would come at a cost to you.

And no, what you’re seeing isn’t standard practice! Keep in mind that what you’re talking about isn’t really about ChatGPT; it’s about incompetence. If your boss were competent, it wouldn’t matter if he used ChatGPT for ideas, phrasing, etc. The problem is that he sucks at his job, not that ChatGPT is the reason why. (The ChatGPT is an interesting detail! It’s just not the core of the problem.)

So what should you do? To a large extent, it depends on your sense of how things work at your company. Since others are noticing your boss’s incompetence too, is yours a company where higher-ups are likely to take a closer look at his work soon and to handle that effectively when they do? If so, the wisest course of action might be to simply wait for that to happen and see how things play out once it does. On the other hand, if your company historically drags its feet in dealing with problems and incompetent managers stay for years, you’d need to decide what the impact will be on you professionally if you keep working for him. In some jobs, he’d be easily sidestepped; in others, it would affect your day-to-day quality of life and your career progression.

There’s also a middle ground, where if you have the ear of someone senior, you might be able to discreetly tip that person off about what’s going on and trust that they’d handle it. (And again, we’re talking about the overall incompetence, and not ChatGPT itself. That doesn’t mean you shouldn’t mention your ChatGPT suspicions if you tip off someone above you, but keep the focus on what really matters: he’s not doing his job well, and that’s causing specific problems X, Y, and Z.)

But raising it with your boss himself is a non-starter since he’s shown he’s unlikely take it well.

Read an update to this letter

{ 256 comments… read them below }

  1. Justin*

    Again, the problem is him being bad. Because ChatGPT is like if Wikipedia didn’t have citations or edits.

    1. Alton Brown's Evil Twin*

      Exactly. In the before times (ie, 2018) he might have just downloaded a project plan from somewhere, done find/replace on a few key words, and sent that to OP. It’s the same behavior, just a different tool facilitating it.

      1. Bruce*

        Back in the 80s our medium sized company was sued twice by a much bigger company. When we received the second lawsuit our CEO noticed that the wording was familiar. He pulled out the brief for the first lawsuit and realized that the same law firm had taken their previous brief, made a few edits and used it for the second brief. Their problem was that he found a lot of embarrassing mistakes where the wording made no sense for the second case… so he _GLEEFULLY_ printed out a copy of both briefs, marked them up with a red pen, then sent them to the CEO of the opposing company. The second suit was dropped, they settled the first suit fairly quickly, and he went on to brag about it publicly and in company meetings. I have a lot of feelings about that CEO, but he was definitely very smart, with a great memory and attention to detail. He was not someone to miss a screw up like that…

    2. Saturday*

      I would have thought that when talking about the issue with someone senior (if the LW chose to do that), it would make sense to bring up the use of ChatGPT though.

      The other issues (unclear communication, bad planning, etc.) sound like things that could improve with experience. But using ChatGPT to this extent just says the guy is not even trying to do his job, and that would be important to know.

      1. Alton Brown's Evil Twin*

        There can also be security and confidentiality risks with using ChatGPT this way.

        NB: this depends on which public-facing tool you’re using. I **think** that Microsoft has more protections about that stuff than others, but it would bear looking into regardless. Not a good idea for your boss to use prompts that include confidential information of any kind.

    3. ecnaseener*

      This is one of my favorite AAM lessons! When you’re faced with a bananacrackers situation, ask yourself “would this matter if the person were competent?” and marvel at how often the answer is “huh, I guess not.”

        1. SheLooksFamiliar*

          My talent acquisition team uses ChatGPT for a lot of things, and most of them have to do with information gathering and synthesizing. However, the team uses the information for their work, they don’t present it as their own. ChatGPT is a tool, not a slot machine that dispenses final work on demand.

          A very smart man once said, ‘Information is not knowledge. The only source of knowledge is experience. You need experience to gain wisdom.’ Words to live by.

          1. AnotherOne*

            My office is starting to talk about using ChatGPT- some other companies in out field have started doing it so we’re looking into it.

            But as exactly that- a tool. Not to replace us thinking about a thing.

          2. NotAnotherManager!*

            This is how I use it. I suck at coding, and ChatGPT has helped me to script things I need to get done because, while I can describe the actual problem I’m trying to solve and the steps I need the program to take, I simply don’t know how to do it in VBA, JavaScript, Python, and all the languages our various programs will accept. Once ChatGPT gets me started, I can add additional prompts/info and then mod it to get what I need and to fit my project – but I’m also very upfront with people that I use it to help me write code.

            1. Justin*

              I used it to help generate discussion questions from a (separate) text I was using. Because it didn’t need to “know” anything to spit out that sort of thing, and I was going to take forever to do so. But I told people I was doing that!

            2. Bruce*

              My employer uses AI for code generation, it has a place as a tool. We do not use it to write reports though.

          3. Jack Russell Terrier*

            As a Historian, I don’t use it for facts or evidence. It’s been known to make things up – including legal cases – see Washington Post article

            ”“I was over the moon excited for just the headache that it saved me,” he told The Washington Post. But his relief was short-lived. While surveying the brief, he realized to his horror that the AI chatbot had made up several fake lawsuit citations.’

      1. Caramel & Cheddar*

        I do think this is one where the answer is still “definitely yes”, but I might be more skeptical of ChatGPT even as a transparently used tool than the average person. Even if this guy was the most competent person on earth, LW says he’s using it for changes in business strategy (!), which feels like consulting the oracle at Delphi to me more than it does making informed decisions based on actually knowing and understanding your business.

        1. Spiders Everywhere*

          If he was using it as part of the brainstorming phase that’d be one thing, the problem is that he seems to be passing the output on without applying any sort or critical thought to it, which would be a problem no matter where the material came from.

  2. Escapee from Corporate Management*

    ChatGPT is like many tools. A competent user creates worthwhile things using it. An incompetent user can cause damage with it. Your boss is that incompetent user.

    1. Random Dice*

      Bro-y startups have a hard time resolving issues professionally, because people are young and everyone is wearing multiple hats – there isn’t necessarily HR, and if there is the execs haven’t learned all the lessons the hard way yet.

      Sometimes a perfectly aimed nickname that encapsulates an issue breaks through even the bro-iest startup. (As ill-advised as that usually is.)

      If his name is Frank, say you heard someone call him FrankGPT. I’m guessing it’ll catch on quick.

          1. Not Tom, Just Petty*

            Ladies and Gentlemen, the Burn of the Year.
            Arriving before noon on January 2.
            Go home, interwebs. We are done here.

    2. zuzu*

      A former boss of mine is that incompetent user as well. He viewed tech as toys to play with, rather than tools to use to an end. As a result, he would just adopt the latest tech for his classes without really thinking about how to integrate the tech into the skills that had to be taught or how the tech would serve those using those skills/tech in practice — and the rest of us would be dealing with a lot of very puzzled students who didn’t know how to do legal research or use tech very well. But thought he was a swell guy nonetheless, because he is very personable unless you’re a woman who works for him and challenges him.

      By contrast, the school hired a director of innovation who actually barely used tech at all in his programs – his approach was to think about ways to really think about making the processes involved more efficient BEFORE you start adding tech, and only add tech if it’s going to assist in that efficiency. He emphasized that you really needed to know how a legal practice worked fundamentally before you could know what kind of tools could be used to change it.

      1. Tinkerbell*

        One of my friends had a co-worker monopolize a routine team meeting a few years ago because he’d heard about “this blockchain thing” and wanted to see if it could be applied to their project. Which involves missile defense systems. He was senior to everyone else on the team and it took a good half an hour for everyone’s “hell no” to get through.

      2. Escapee from Corporate Management*

        I took my intro Management Information Systems course from a leader in the field. In the first lecture, he said we would not be discussing specific software, applications, or tools in the class. Multiple techies expressed puzzlement about how this could be the case. The professor replied that this course was about identifying problems and outlining systemic solutions, not about tools. Tools were only useful once the planning was complete.

        One of the wisest professors I ever had.

      3. Freya*


        I get people telling me AI should do payroll, so they don’t have to wait for a human (me) to get in and check their timesheet before they get paid. Unfortunately, even if AI could do payroll, they still wouldn’t get paid when I’m not at work due to a public holiday because banks don’t process payments on public holidays anyway!

        (I have to check their timesheets, because they do silly things like copying and pasting the previous week’s timesheet without considering that there was a public holiday in their state, and since the project they’re working on gets on-billed based on timesheets, it’s got to be correct wrt billable and non-billable or the timesheet gets rejected)

  3. nnn*

    Mercenary option: when you want to get a specific response out of him (permission/authorization to do something, etc.) run a few phrasings through ChatGTP to see which one elicits the desired answer.

    1. JSPA*

      This is downright brilliant (if you want to stay).
      If you want to bail, maybe run the wording to figure out what will prompt him to give stellar severance–then leave, and don’t look back.

    2. Richard Hershberger*

      I like the cut of your jib! At least in theory. I suspect in practice this guy is so all over the place that getting the response you want today won’t mean much tomorrow.

    3. Dulcinea47*

      this is literally nightmare fuel. I don’t want to spend the rest of my life massaging ChatGPT to get results I want.

      1. Eldritch Office Worker*

        It is, if widely utilized. In this case it seems more like martial arts where you use your enemy’s strength against them. Of course it’s not a real strength, but it’s the center of his balance for sure.

    4. ferrina*

      You can cut ChatGTP out of the equation and just write what you want yourself (mimicking the ChatGTP/”boss” s voice). You already know that the boss is happy to use other people’s work as his own, so just make it easy for him to use the work you want him to use.

      I did this for over a year with an incompetent boss. She had been promoted way beyond her capabilities (nepotism promotion: they actually removed requirements from the job description so they could give her the job). She had no clue what to do. Even worse, I was the most senior and knowledgeable person there, so she was ready to see me as an enemy. But I had a plan:

      Step 1: Be the most kind and supportive employee. Be excited for her. Ask how I can make her job easier. Be super communicative. If needed, make a couple off-hand remarks about how I was glad to be doing my job so I could “really focus on [thing I’m excited about]
      Step 2: Provide ideas and sample documents, positioned as “gee boss, I’m not sure about this, what do you think?” My ideas were positioned as “I just brainstormed this” when it could have been something I’d spent a couple hours laying out and troubleshooting. My “sample documents” were proofed and ready for widespread release. Always positioned as something where I was eagerly awaiting her leadership. That way the only thing she had to do was pretend to look at it and say yes.
      Step 3: Quietly take away work that they won’t miss. I would offer to take on tasks that my boss hated, and she happily gave away most of her job to me. She was happy she didn’t have to work, and I was happy she wasn’t screwing things up.
      Step 4: Leverage my new accomplishments to get a better job. I did a great job doing my boss’s job, so I updated my resume with all the accomplishments from things I had led. I landed a new role doing the same thing as my boss at a better company. As a bonus, my new role was making much more than my boss. As karma, without me my boss floundered and had 80% turnover in her department in the next year.

    5. Ozzac*

      A great option. Or just have chatgpt “chat” with your boss during meetingswhile you do the actual job

  4. Czhorat*

    The desire to coach him is laudable, but you’re not responsible for helping your boss develop his career; it’s usually quite the opposite.

    As far as the trick he’s trying to pull, it seems sitcom worthy in its absurdity; I can’t imagine that others haven’t noticed that his work output is bizarrely paced and just strange, even if they haven’t connected the dots to know that it’s ChatGPT.

    With a boss who is not welcoming of criticism (likely because he lacks confidence, which is likely because he isn’t actually doing his hob) I’d stay in my lane and wait to see how it plays out.

    Grab some popcorn if you want .

    1. HonorBox*

      Don’t disagree at all. But it may depend on the setup of the business. If the boss has bosses, it is not if, but when, they figure out that the boss isn’t qualified. If there are not direct supervisors, it might be more sensible to seek out help, or just start looking for another opportunity.

      1. Not Tom, Just Petty*

        “Others are also noticing and mocking him behind his back.”
        Someone upstairs is going to find out.

        1. Pastor Petty Labelle*

          Someone upstairs may already now and not care. Hey its a start up — move fast and break things. So why not use Chatgpt to run the business, it has to improve things RIGHT? Its technology, so it must be good.

          1. Czhorat*

            Yeah, but eventually someone who he can’t put off will ask a question that he needs to answer *now* and not an hour from now when he’s had time to hide in his office, log into his chatgpt account, and have it create one for him.

            You can’t keep this act up forever.

          2. Not Tom, Just Petty*

            New = Better.
            His critics just don’t understand the world today. He’s a pioneer!

    2. Observer*

      y; I can’t imagine that others haven’t noticed that his work output is bizarrely paced and just strange, even if they haven’t connected the dots to know that it’s ChatGPT.

      You are surely right. The LW specifically mentions that others are noticing the incompetence and mocking him.

    3. AnonInCanada*

      While I don’t disagree with you in that respect, OP better be cautious, because when this boss inevitably steers his transport truck of a career into a barrier or off a bridge, OP may find themselves in the path and careen into the abyss with him. OP may best to take notes to give to HR in case that happens (assuming there is an HR there, but I’m sure this boss has a boss to present their case to.)

      Unless the boss’s boss is Skynet, and it’s becoming self-aware. Then this’ll be the least of OP’s worries. (Insert theme from Terminator 2 here.)

      1. zuzu*

        I can’t help but think that anyplace that puts a kid who’s fresh out of college into a management role doesn’t have much of an HR department.

        1. Kesnit*

          If OP didn’t say it was a start-up, I would be thinking military. New O1’s sometimes feel like they have to be “the officer,” rather than let their senior enlisted be the voice of experience. (I say that as a former “new O1” who made that very mistake.)

          1. Not Tom, Just Petty*

            Ahhh. My favorite.
            The boss who bosses very boss-ly.
            Not bossily. that is a different thing. Bossing very bossly. Or officering very officerly.

          2. Reluctant Mezzo*

            Even as a lowly butterbar, I sought wisdom from the oldest enlisted, even if he sometimes mistook me for a Girl Scout (I really did look 15 at the time).

  5. Wordnerd*

    Does the headline mean to say “I think my boss is using ChatGPT”? I was expecting a question where there wasn’t a human boss at all.

    1. FricketyFrack*

      I assumed it was meant like, “my boss is using ChatGPT to the extent that it might as well be my boss.” But now I’m thinking about some kind of nightmare where ChatGPT decides it wants to run a company and starts one so it can.

        1. FricketyFrack*

          You know, if Skynet paid well and had halfway decent benefits, I’d have to really think about that. How much time off does our artificial overlord give?

          1. Not Tom, Just Petty*

            This reminds me of the debate Randall had with the contractor in Clerks. “What about the innocent people like welders and painters and food service who were on the Death Star with Luke blew it up? Aren’t they innocent victims?
            So yeah, there is a downside. Will workers’ comp cover if the rebel forces take down Skynet and beaten by a rogue reprogrammed water dispenser?
            Cuz I can work with that.

            1. Random Dice*

              When my son imagines being Baby Yoda and blowing up the Death Star — yeah, he’s a bit confused — he always calls for an evacuation first.

              (Heart-eye emoji)

              1. zuzu*

                Oh, they had their chance to evacuate. But it was their hour of triumph!

                Doomed by bad bosses.

                And let’s not forget all those welders and whatnot were still serving in the Imperial forces, so they might be grunts, but they have some complicity.

            2. Beany*

              I started reading Mistborn by Brandon Sanderson (not a new book; I’m late to the game), and one of the main characters is pretty blasé about all the lackeys and servants (bot necessarily fighters) he’s been killing while on his mission to take down the big bad empire. As far as he’s concerned, they all chose the wrong side by serving the real baddies.

              1. Random Dice*

                Like the book Hench, which I learned about here – heroes can leave a trail of destruction in their wake.

                1. Not Tom, Just Petty*

                  Like the first Henry Cavil superman movie. Like come on, you brought your civil war here and destroyed cities and killed people.
                  OOoooh, I remember the thread about that. I have to read it.

              2. Reluctant Mezzo*

                When my dad was in WWII, he always made sure the regular Wehrmacht guys were escorted to the POW camps. He figured if he’d be born in Germany, he would have been one of their dogfaces too. But the SS? You had to volunteer for the SS, so he always let the partisanos (Italy) ‘escort’ them.

          2. Arts Akimbo*

            Oh, man… someone really needs to do a sci-fi dystopia where the machines are killing the humans but if you want good health insurance and medical care you have to go WORK for them! Do you sell out your species in exchange for physical safety and well-being? Once you’re inside the system, how dystopianly awesome or terrifying is it? How many mistakes are you allowed on the job before you, too, get terminated? Is the job interview literally do-or-die? Are there humans who try to take down the system from the inside?? I really wish I could write, LOL!

            1. Hlao-roo*

              This isn’t quite the book/movie you want, but have you read Hench by Natalie Walschots? It’s about a woman who does temp work for supervillains (so, not for killer robots) because they pay better than non-supervillain temp work.

            2. Kara*

              You could probably take the biography of any grunt working in the oil or tobacco industries and throw in some sci-fi elements and there you go.

        2. Red Reader the Adulting Fairy*

          Housemate, many moons ago: “Why do you always say thank you to Siri? It’s not listening anymore.”
          Me: “So that when she and Alexa and Cortana and whatever Google has get their collective nonsense together enough to take over the world, maybe they’ll remember that I was always polite.”

    2. Festively Dressed Earl*

      Nope. Alison is subtly signaling that LW’s boss is a poorly programmed robot overlord.

    3. MassMatt*

      This is completely where my mind went, the boss doesn’t exist at all and is simply an empty suit placed around a program. I also thought the “person we hired is not the person we interviewed” letter from months ago could be taken two ways–but in that case, it seemed they were literally not the same person!

      Info needed–LW, have you actually SEEN the boss, either live or at least virtually?

      The work place can be so bizarre we need to conduct ID checks and Turing tests to determine whether the employees are even real!

      1. sacados*

        It’s the hitech version of that different person scam — the actual person interviews and gets the job, then they set ChatGPT loose to do all the actual work while the person can goof off and/or work a second job simultaneously!

    4. CB212*

      Tons of bosses are USING ChatGPT for all kinds of things. I think the joke is, there’s no “there” there – ChatGPT is in fact all the substance of the kid’s ideas as well as language.

      1. Jaydee*

        Right. This is a Wizard of Oz situation. You see a human boss with a human name and a face. But when you look behind the curtain it’s just ChatGPT.

    5. NerdyPrettyThings*

      The title is absolutely the best thing about this post. If it’s an error, Alison, please don’t ever fix it. This boss has nothing of substance; all he has to offer is ChatGPT.

      1. But what to call me?*

        Yes, the title is perfect.

        The human boss is only ChatGPT’s avatar. Chat GPT is the real boss.

  6. Aswin MK*

    Just a curious question, you say your boss is out of college? Has he/she graduated from a prestigious university (Say Harvard) and hence got appointed to a Managerial position directly? I am just confused as to how a boss (Who is supposed to have some form of tenure and some level of expertise) can commit such a basic error.

    1. ThatGirl*

      It’s a startup, so he just had to be competent enough to attract investors and/or a board. May not have been anyone to appoint him.

      1. Smithy*

        This reminds me of the letter last year about the internship with the start-up that could lead to a job. Intern well for the start-up while in university, and then if the investors come on while interning competently – boom, there’s the senior level job right at graduation. It’s one of those right place, right time jobs that can easily get you “over your skis” based on the growth of the start-up and having nothing to do with your readiness for that kind of a job.

        The plus/minus of being the person who takes that job I think is just so hard to balance out. Let’s say this guy is really aware of how badly he’s doing, but he’s making great money and is planning to go back to grad school in the fall. So he’s just really looking to hold on until the summer, and then will have a savings for some travel, do grad school and restart a career so these connections aren’t as important. The other side, is that if this is the desired professional pathway, and so it’s about trying to hold on as hard as possible to credibility and networks that do exist – it can incentivize some really unfortunate behavior.

        1. Texan In Exile*

          I know of one female start-up exec who’s in her 20s. She was college friends with the two male white founders.

          She was able to leave her corporate job for a start-up because she had no school debt, she was on her parents’ health insurance, and I suspect her parents helped her with the bills.

          I read that the one thing successful entrepreneurs have in common is that they come from wealthy backgrounds. I believe it.

          1. ArtsNerd*

            Yup. Back in the day I had an ex who lived with his parents when he worked for an early-stage startup. No salary? No problem – he also had no bills or debt, thanks to his parents’ support.

            He got bored and left that gig shortly before they launched the product (and started bringing in revenue.) He couldn’t understand why my brain was exploding at the very responsible and exceedingly clever choices he was making. He seemed baffled that more people didn’t take advantage of this obvious cheat code to inevitable wealth and success.

            I had VERY mixed feelings when that company became a household name, lol.

      2. fhqwhgads*

        Right, exactly, but also to OP’s question: not only is this boss’s extensive use of ChatGPT not normal, it’s also not normal that someone’s first job out of college would be a boss. And startups are their own world of weird. So no, this situation isn’t normal in a whole lot of ways.

      3. TechWorker*

        But still, a startup having someone managing entry level positions is one thing, someone ‘very early in career’ managing someone in an executive level position.. is weird, right? Unless executive position also does not mean what I think it does?

    2. SansSerif*

      I was wondering why they took someone right out of college and made him the boss of someone with much more experience. It’s like he’s set up to fail.

    3. Richard Hershberger*

      Yup. The buried lede is that the LW is in an executive position and has a boss just out of college. It would be one thing if he were a wunderkind, but this clearly is not the case. I’m just saying, don’t rely on an equity stake rather than salary.

    4. Jam on Toast*

      I’d put money that they were a serial plagiarizer in college, too. I’ve spent 15 years in higher education, and most times, when I uncovered a breach, retrospective scrutiny of a student’s earlier class work would show that it too was academically dishonest as well, or that they’d been caught in other classes. Many college transcripts now include a record of confirmed academic breaches, as well, such as FI (failure due to academic integrity breach) which could be another avenue if the higher ups begin to investigate the accuracy of this person’s credentials and skills.

      1. Dulcinea47*

        Yep. You don’t get out of college without knowing how to do your own work unless you’ve *never* doing your own work, and possibly don’t even understand why you should.

    5. Slow Gin Lizz*

      I was also curious about this. I’m guessing he’s some kind of genius with expertise in exactly the area the start-up needs expertise, but it’s absolutely wild that they would immediately put him in a *managerial* position. I know start-ups are often quite wild, but this is next level, IMO.

      1. ecnaseener*

        If he had any genius or expertise, he’d be able to use the chatgpt text properly (ie discarding bad ideas and tweaking good ones to make sense), which he clearly isn’t. He probably knows the founders from school or something.

        1. Slow Gin Lizz*

          What I meant was, he might be a complete genius at nuclear physics but has no idea how to use chatgpt in the manner you are suggesting. And therefore his company is overlooking the fact that he’s an inept manager because they need his physicist brain. And therefore, also, the company is inept because they have this guy managing *anyone.*

          1. ecnaseener*

            I’m saying it’s not about not knowing how to use chatgpt specifically. If he’s a genius at nuclear physics, he can look at a piece of text he generated for his nuclear physics work and say “oh that’s incorrect” or “that’s incoherent” or “that’s a good starting point, let me just rewrite this bit here to make it make sense in my company’s context.”

        1. lw*

          Yeah. On my first day I noticed “Elon Musk” written on a whiteboard with no context. That was, uh, an omen.

    6. lw*

      LW here- this is a case of friends bringing in friends. When I accepted the position, I assumed there was a reason beyond that for his position (which there might be, just one I have yet to experience). I also felt like I might have been being unfair and ageist when I interviewed with the company and had some hesitation about the relative lack of experience. I resigned from this job today when it became apparent that this wouldn’t get any better.

      1. Richard Hershberger*

        I wonder if you weren’t brought in to be the adult in the room, but with lower pay and title.

        1. lw*

          OP here- I think, on a subconscious level, there was some of this. Shortly after I joined, I discovered a similar pattern had been taking place in other areas- hiring someone experienced/[things happen]/they are unceremoniously fired or resign (usually fired). I think there’s a push/pull of knowing that they need guidance but not being willing or able to take it for whatever reason. It’s tough and I think I would have been a shitty leader at that stage in my career.

          I have a new thing lined up, and I think it’ll be a refreshing change of pace. I knew I was taking a risk by joining this organization, and that’s how it goes sometimes! I feel fortunate that I was able to excuse myself when it became apparent that it wasn’t a workable situation, especially in this market.

          1. Random Dice*

            I’m really impressed with you! Well done, trying something new, but also having the courage to leave when it showed itself to be too broken.

    7. Qwerty*

      It’s a young startup. Odds are the boss is either one of the founders or one of the first employees hired. OP is in an executive position, so their boss must be a senior executive.

      It’s the risk one takes with a job like this.

    8. Kara*

      Earler this year a lawyer got caught submitting a brief that had been written by ChatGPT. It was noticed because the AI made up all of the cases and citations in the document. Experienced lawyer, quite capable of writing a brief on his own. But he followed the siren call of the AI anyway.

  7. HonorBox*

    I hope upon hope that there is someone above your boss who you can bring this to. It will be tricky, not only because you don’t want to just level an accusation of your boss relying solely on ChatGPT, but also because you know your boss doesn’t react well to feedback, and probably will bristle at feedback that comes from someone higher up too. But if you do have someone who you trust, it might be helpful to have others go with you too. Focusing on the inability to lead versus use of ChatGPT is going to be your best bath, though I wouldn’t shy away from sharing what you’ve learned about the possible use of ChatGPT, too.

    1. Zelda*

      An organization that’s *willing* to hire someone just out of college with no previous professional experience to be a manager is not one that I trust *at all* to see the problems here and act effectively or appropriately. Hiring such a person as a highly-paid SME, or even as a technical team lead, totally plausible. But I don’t for a second think you can be a good manager of people without ever having been a team member. Even having served under a poor manager will give a person a great deal of information about what needs to be done, and even about how to do it, if only by negative example.

  8. Rose*

    A former boss was CONSTANTLY touting how awesome ChatGPT is, and was using it for everything. Then one day he had to host an all hands meeting to announce layoffs, and it was extremely clear that he used ChatGPT to write his speech, and several people called him on it. It was just the absolute worst thing he could have used it for. He sounded like a robot telling 40 people they may not have a job at the end of the day.

    He apologized for being impersonal, but the apology was also clearly written by ChatGPT.

    1. king of the pond*

      I have to know how the apology went down. Did he have it ready ahead of time? Did he quickly write “how do I apologize for laying people off via ChatGPT” into the bot and just read off the result there and then?

    2. t-vex*

      That’s awful but I actually did use Chat GPT to help me craft a message about an employee that was leaving. I was having FEELINGS about it and really trying to come up with a way not to show it. I edited the script to fit my own style but it actually was helpful in getting the tone right.

      1. Yvette*

        “I edited the script…”. That’s the difference. You didn’t just cut and paste whatever ChatGPT spit out. That’s how it should be done.

        1. Siege*

          Yeah, my boss used it for a part of a speech once. We didn’t more time editing that one section to get the flabbiness out of it (not really overly-adjectival or anything, it just felt like a lot of the word choices were heavy in the mouth and with a lot of round sounds – it’s hard to describe but flabby feels most accurate) and get it to sound like her that she hasn’t done it again. I think we spent more time on that section than the rest of a 30-minute speech.

    3. Lacey*

      Ugh. My boss LOVES chat gpt and has started using it for all email communication.

      Sometimes it spits out something coherent, but so often it sounds like someone talking about the subject in the abstract when we need concrete answers to specific scenarios.

      1. Bread Crimes*

        This is how I spot it when my students use ChatGPT to write their essays. (Aside from the way their punctuation, capitalization, and spelling improve while their factual accuracy plummets.) Lots of big sweeping statements, bland “both sides” approaches to arguments, and very few specifics. If it’s bludgeoned into stating specifics, they’re usually outright wrong. It’s maddening, because it’s got just enough overlap with how anxious students with high technical proficiency and shaky grasp of the material will write that I often spend a lot of time trying to provide a careful and useful critique before I realize I’ve wasted my energy on extruded language product.

        1. Zelda*

          “extruded language product”

          Excellent turn of phrase. Possibly useful as a tool against those who think this sort of AI is actually “intelligence” of any kind, or that it is “creating” anything.

          1. Richard Hershberger*

            It likely is a play on “Extruded Fantasy Product,” used back in the ’90s to describe the torrent of fantasy novels that read like mediocre writeups of mediocre D&D campaign.

    4. nen*

      The leader of our organization uses ChatGPT for everything like this, openly and without apology. It is so embarrassing and obvious.

  9. Just Thinkin' Here*

    So you are in an executive-level position and wondering what to do? If your manager is the CEO, get a new job. If the manager is not the CEO, go to above them or to the CEO and tell them what is going on. I agree – the ChatGPT is a symptom and not the real issue – the real issue is that this person can’t function independently and is way over their head. A start-up needs to know that because anyone who is managing executive-level people should be able to function at the executive level themselves. Start-ups are already risky ventures, they need competent people at the helm.

    1. lw*

      LW here! My boss & the CEO are old friends, and I think I was so put off by the symptom and my own lack of experience with using AI for these kinds of purposes that I wanted to make sure I wasn’t missing anything before deciding how to move forward. I decided to get a new job!

      1. Observer*

        d I think I was so put off by the symptom and my own lack of experience with using AI for these kinds of purposes that I wanted to make sure I wasn’t missing anything before deciding how to move forward

        That’s a smart move. It turns out that you are 100% correct that this is baseline incompetence. But when you’re faced with something this new, it’s worth double checking that it’s not clouding your judgement.

        So, good for you! And also, good for you for going for a new job.

      2. Just Thinkin' Here*

        Ooof. :( It’s really unfortunate to walk into that situation – because really there wouldn’t be much you can do. If the CEO brought in this inexperienced guy to manage other executives, then the Board of Directors is probably also made up of friends who are equally inexperienced.

        As for AI, most companies in my industry are discouraging use because they don’t want employees uploading or sharing anything that could be trade secrets, products under development, market research, computer code, or other non-public information. Running emails through ChatGPT could mean that internal information gets out into the public domain. Most large companies would frown upon this behavior and take action to squash it.

        Good luck on the job hunt!

  10. Skytext*

    How does someone right out of college get such a high level job when he’s so incompetent. Boggles my mind.

    1. ZSD*

      I was wondering how anyone straight out of college, generally competent or not, got such a high-level job. My theories are 1) this boss is the CEO/founder of the startup or 2) nepotism/cronyism.

      1. mango chiffon*

        This is what I was assuming and to me seems like a sign to get out while you can. It’s a bad sign if this is happening, people are aware, but the CEO/founder (if not the boss) is not doing anything about it.

        1. MassMatt*

          Very bad sign when people are joking about his incompetence yet no action seems to come from upper management. Unless the boss is careful in communicating to his superiors and simply using AI for his underlings.

          Still awful, but people who are terrible are often very aware of who they can and cannot be terrible towards.

        1. Liane*

          Nepotism, cronyism, and owner-founder-itis are often co-morbidities of mediocrewhitemanitis. A term I like by the way.

    2. Impending Heat Dome*

      That’s what I was thinking. LW is executive level, this dude is their *boss*, but uses ChatGPT to do his job? Because, understandably enough, a kid straight out of college will have no idea how to run a company?

      Get some good resume fodder for a year or so and then split.

      1. Leslie S. Weekly*

        My reaction to the letter was that the biggest problem is it’s their boss’ first. job. out. of. college.

        Oh I get how this happens, btdt, but it’s a very red flag, particularly for those working under such a manager.

        Sincere good wishes to the LW that they find a solution either in their current position or elsewhere.

  11. NoOneWillSeeThisComment*

    The title seems to be “missing” the word ‘using’ – which makes for a much funnier concept. Was low key disappointed to find boss is, in fact, a real person.

    1. Butterfly Counter*

      Well, I think that “using” in the title wouldn’t get to the core issues of the OP’s problems. Lots of people use ChatGPT and use it in a way that actually works. So what? But OP’s boss is using it to the point they aren’t doing anything else. So, in a sense, OP’s boss is ChatGPT. So Allison’s way is more accurate.

    1. gyrfalcon17*

      Subject: Update on “I think my boss is ChatGPT”

      Dear [Recipient],

      I hope this message finds you well. Since my last communication, I’ve continued to observe unusual patterns in my boss’s behavior that align with ChatGPT characteristics. The responses in meetings remain highly structured, lacking personal anecdotes or emotions. Additionally, there’s an uncanny ability to generate diverse, contextually relevant information on various topics.

      I’ve discreetly probed with ambiguous questions, and the responses still echo the distinctive style of a language model. While I can’t definitively conclude that my boss is ChatGPT, the evidence is intriguing. I’ll keep you posted on any further developments.

      Best regards,

      [Your Name]

      1. AnnieB*

        Interesting that ChatGPT thinks its main problem is the lack of personal anecdotes and emotions, and that it stands out by being so knowledgeable and having so much relevant information. I have to say, when I used ChatGPT to do something standard in my job, it was only notable in how superficial it was.

        1. Zelda*

          (If you want to tell any stories about the “worse,” I’ll go make the popcorn. Understandable if they’d be too identifying or if you’re just over it, though.)

      1. SarahKay*

        Sorry to hear you were right, and it got worse.
        Delighted to hear you have a new job; I hope your new job and new manager are both (at the very least) a huge improvement, and ideally actually good.

      2. AnonInCanada*

        We need updates! Please! I have plenty of popcorn to hear what our new cybernetic overlords are telling this “boss” what to say and what to do.

        He has become the Borg. He has been assimilated. Resistance was futile, but I presume he didn’t. And I’m happy you escaped the black cube before you turned into one as well.

    2. Observer*

      The OP has already updated. They have decided, reasonably! that this is not going to get any better, and they are getting a new job.

      OP, do let us know where you land, though.

  12. Smithy*

    As AAM said, this is just a modern wrinkle to a boss in over their head, and ChatGPT is their attempt to compensate for feeling insecure and unable to do their job. So ChatGPT is helpful as the illustrative example, not the problem on its own.

    I will say, that like many of us who’ve had bad or incompetent supervisors – it can get easy to have tunnel vision on that supervisor as the key problem. But, I think it often misses the larger point of who is over that person and what’s happening there. And if you realize that the grand bosses or the board or whatever other management system in play either like your supervisor, don’t mind, are averse to change, or any other approach that ultimately means that person isn’t leaving – then just do what you need to do to protect yourself while you’re there and look to move on.

    People end up in jobs over their head enough of the time, and while good places don’t always rush people out the door – there should be avenues to indicate that something isn’t going well. If there is no path for that, that’s telling you something and making it your job to fix it is opening to the door to grief that will rarely pay you back.

    1. Ama*

      Years ago I had a boss who quit abruptly and then it was discovered she was paying freelancers to produce work she claimed to be doing herself (she quit because we were about to have an audit and she realized she’d have to explain what those expenses were).

      I find myself wondering what kind of shenanigans she would have gotten up to if ChatGPT were available back then.

      1. econobiker*

        Boss paying freelancers WITH company’s/organization’s money and claiming work was her own? That is super harsh – and so obvious.

        She was not astute enough to pay out of her salary and conceal it like that computer programmer who outsourced his work offshore and kept up the front until an audit of his security key’s physical location revealed his ruse.

  13. Antilles*

    This exact guy has existed for decades in Corporate America, the only thing different is the means. In previous generations, he’d be doing the exact same thing with project plans, strangely shifting business strategy, and so forth.
    It’s just that previous version of This Guy would be making said decisions based on whatever corporate buzzwords he happened to read on a website, hear on the radio, or see in a newspaper that morning.

    1. Yeah...*

      New technology has way of making people think many old problems are new. They are not, just the mechanisms to bring them forth.

      1. Smithy*

        Honestly. Lots of team or department strategies I’ve had over the years for are copy/paste jobs from previous strategies with minor tweaks here and there to include new buzz words, phrases, or just synonyms to make it not looks like a direct copy. But they’re a copy/paste of a copy/paste, of a copy/paste.

        Over time, you do that enough and those strategies 100% do not make sense, are entirely contradictory, and if you push back through the jargon slightly make zero sense.

      2. Weaponized Pumpkin*

        I keep having this conversation about social media. My father blames all the conspiracy theory stuff on it — well, no. Remember the moon landing? JFK? Nigerian prince scams were sent by fax once upon a time. Hell, people fought against the vaccines and sold snake oil in the past, too. Cons, conspiracies, and lies have always been around.

        Social media (and, really, the internet) certainly does amplify problems and allow misinformation at scale and speed. But the behavior is not new.

    2. Quinalla*

      Yup, same problem, different tools being used to try and compensate. Sounds like this dude is way over his head and thinks he can’t/shouldn’t ask for help. Yikes!

      Also, want to point out ChatGPT can be a great tool, but it shouldn’t be used like this! I was going to say “obviously”, but it isn’t obvious to this boss anyway. I use it a lot, but I don’t use it to just generate emails/plans/schedules/etc. without heavy editing. Like I said, great tool, but you have to know how to use it. Kind of like search engines when they first came out (or still honestly, so many people can’t use them well), some folks had no clue how to do a good search and over time, search engines have improved a lot too to account for folks not knowing how to make good prompts. Most folks don’t know how to prompt properly and re-prompt, etc. to get what they need out of ChatGPT and the one “training” I went to on it was very light on this topic and it is the #1 thing I think folks need to know how to do with ChatGPT – not typically all the whizbang image creation stuff that is very niche :)

  14. mango chiffon*

    Gosh if you’re in an exec level position and this is your boss, is there even anyone significantly above him? Honestly wonder if it’s best to just start job searching. I can only assume the boss is involved in the company’s creation, or the CEOs/creators of the company are not aware enough of what’s going on, which are red flags to me.

    1. BradC*

      Yeah, that’s what I was wondering as well. Is this a founder or co-founder of the startup? Is this the CEO or a board member? Owner or co-owner?

      If so, I’d be concerned not just about this one person’s competence, but about the direction of the company as a whole.

      1. Slow Gin Lizz*

        Agreed. This company doesn’t seem to know anything about how to run a business. I’m already dying for an update to this letter.

    2. Phony Genius*

      Yes. You also have to think about whether this is the type of company that allows executive managers to hire their own people and get rid of executives who worked for the previous manager. Understand that this decision is more difficult since you are a new executive (or at least new in this company).

    3. lw*

      LW here. Yeah, the situation is that there isn’t anyone significantly above him. I ended up resigning after a few more situations like this.

  15. Pastor Petty Labelle*

    You stated this is a youngish start up. Already your boss is showing his incompetence. Now whether your boss is the CEO or not might matter, but its clear that people in authority are incompetent. I do not think this start up is long for this world. I would be looking for a new job not trying to save my boss’ career. Put your own mask on first. If this place shuts down — like a lot of start ups do — what you have done to save your boss’ career won’t help you.

    1. lw*

      OP here- you are exactly right. I wish all the best for them, but the thing I did after I wrote this letter was start searching for something else, which I have been fortunate enough to land.

  16. Juicebox Hero*

    This company being a startup makes me think that the boss has loads of enthusiasm and ideas, but has no clue as to how to handle the actual business part of running a business. And furthermore, he knows he’s bad at it so he reacts badly to criticism as a way to keep people from calling him on it.

    And it’s been working for him so far. No one wants to tell him he’s trying to cut through a plank with a screwdriver so he’ll keep on hacking away.

    1. Random Dice*

      “No one wants to tell him he’s trying to cut through a plank with a screwdriver so he’ll keep on hacking away.”


          1. Slow Gin Lizz*

            I rarely see one of your comments here without being like, “Yes! Juicebox Hero is the best!”

    1. The Prettiest Curse*

      Ooh, nice callback! Though the visionary dude wrote in a number of years ago, back when he was fresh out of college. So apparently there’s just an infinitely replenishing supply of this type of person.

      1. Richard Hershberger*

        We don’t know that this guy is fresh out of college: just that this is his first job out of college. It is easy enough to believe that Visionary Guy has been living in his parents’ basement playing video games until landing this sweet gig.

  17. Elle*

    The synchronous/asynchronous meeting part is the biggest source of confusion for me in this letter. Am I to take it to mean that this guy is just not attending meetings?

    1. Hlao-roo*

      Sounds to me like he attends meetings occasionally: “He has … exhibited some bizarre behavior early on when asked a clarifying question … (leaving a meeting abruptly and not returning).”

      I don’t know what exactly his “aversion to synchronous meetings” looks like in practice, but I can easily imagine the boss deploying either “email is more efficient than a meeting” or “I’m too busy to make the meeting, send me the minutes and I’ll email you my feedback” to avoid meetings.

    2. Melissa*

      I’m confused by that too. You can’t generally just say “I never meet with anyone or attend any meetings, but here are some thoughts via email.” If he is doing that, then there are major problems at the organization

    3. Festively Dressed Earl*

      In this case, synchronous means taking place at the same time so that BossGPT has to answer off the top of his head. Meetings, phone calls, Zoom, interpretive dance circles, etc. Asynchronous means there’s a time lapse between communications where BossGPT has time to generate an AI answer. Email, Slack, text, messages written on delicious cake.

      1. lw*

        OP here- this was also one of the most confusing things to me. It means that they rarely attended meetings, and if they did, were “taking notes” and otherwise solving problems by copying/pasting responses into shared agendas. They said it was a generational thing and that synchronous meetings waste time. I know people hate meetings, and this leader and organization seemed hyperfocused on efficiency/productivity, so I initially attributed it to that. Eventually, it got really, really weird, though. I implemented more (structured, intentional) synchronous meetings on my teams, and they went well from my/the team’s perspective, but I got a lot of pushback from the rest of the LT because what I saw as collaborative problem-solving was viewed as “hand-holding.” I think it comes back to the folks in leadership having very little experience running a company that has more than a few employees, but it’s also possible that I have a ye olde timey approach and view of meetings.

        1. SarahKay*

          In that case I’m right there with you in you “ye olde timey approach and view of meetings”.
          Not least because as far as I can see the correct description of asynchronous meetings for any more than two people would be, well, email.

  18. Witt*

    The only thing I would add to Alison’s answer is that depending on your industry, his use of ChatGPT may cause liability or intellectual property risks.

    If he is feeding your proprietary company information into it to generate his business plans, many AI tools such as ChatGPT will then regard that information as their property, and will feed it into other answers that they generate for other users. So it won’t stay secret or proprietary for long!

    (To find out whether he’s giving up control over proprietary info, you’d have to know exactly which AI tool he was using, and what the user agreement says about who owns the data that you feed into it.)

    Conversely, even if he’s NOT feeding it info about your company, if he’s just asking it questions, but then using those questions to generate materials that you all are then presenting to your own clients/customers as original content, then he may be inadvertently plagiarizing or even stealing others’ intellectual property — because many AI models have been trained material that was “harvested” with dubious or no consent from the people who originally created it.

    If your company is a start-up, it may not have a lawyer or risk management department. But this IS the kind of thing that your board and investors should theoretically be worried about. (Depends on how much your company embraces the careless “move fast and break things” philosophy of operation.)

    1. Random Dice*

      Oh good point! Big companies create internal AI engines so their proprietary data doesn’t get out, but I doubt this startup did that. Eep.

    2. Observer*

      There is another liability issue as well, and I think it’s highly likely to bite them given how little review the guy seems to be doing. That is that chatGPT really does “hallucinate”, which means that it states a lot of incorrect things as facts. Which means that it could suggest ideas that are unwise, impractical, illegal or impossible, and it would all be in the same salad.

      Trying to use that kind of stuff can have some . . . interesting results.

    3. Mel*

      Yes, and same if you’re working with anything classified – these are the kind of scenarios where going over someone’s head to flag their ChatGPT use would be serious and justifiable.

    4. worksinpublishing*

      This! Usually I find the perspective of “focus on the wider performance issues not the specific weird behavior they’re producing” to be useful, but in this case I think it’s leading people to overlook that there is a specific liability reason why the employer should want to know that boss is using ChatGPT. Yeah it’s a tool and tools can be used in good and bad ways, but feeding this specific tool any kind of sensitive data could easily create serious problems. Of course, from what OP has said it sounds like the business may be too cavalier/disorganized to take that risk seriously…

  19. Lacey*

    I recently realized my boss has started using chat gpt in situation where he doesn’t feel confident managing.

    Suddenly word salad emails that showed a frustrating lack of reading comprehension made sense.

    But, the problem isn’t really chat gpt (as frustrating as it is) it’s that my boss doesn’t really want to manage the department or deal with any of the problems that we bring to him.

    That was a problem before generative AI, now it’s just an extra wordy problem.

    1. Dulcinea47*

      I like this description- it’s not a *new* new problem, but it’s got new features like the depth and quantity of word salad that people think sounds smart but if you try to parse it, there’s no meaning there.

    2. Captain dddd-cccc-ddWdd*

      The annoying part about that is he’s probably articulated the problem or situation (whatever the issue needing management action is) better and more directly by typing it into Chat GPT using words that could be used himself!

      1. Lacey*

        Yeah. He’s definitely using chat gtp to try and make what he’s saying (mostly “no, I won’t fix this problem”) more palatable. So, it’s serving his purpose. It’s just an extra frustration for us to try and figure out if there’s actual meaning in the words he’s sent us.

  20. Phony Genius*

    Reading this letter and the comments has me wondering how ChatGPT would answer letters written to AAM. Would it train itself by reading this site?

    1. ZSD*

      And it would learn that it got the best response when it started each answer with, “What in the double-fried f**k.”

  21. WorkingRachel*

    I feel like the headline on this was misleading…it’s an interesting situation but not nearly as crazy as the headline implies!

  22. SarahKay*

    Am I the only person who would be fascinated to know what ChatGPT’s response would be if OP were to ask them this question?

    Also, if OP mentioned that they’d normally write to AAM, would the ChatGPT response include teapot-making llamas?

    1. mreasy*

      chatGPT’s answer:

      Dear Concerned Executive,

      It’s certainly a unique situation you’ve uncovered. In addressing this, I recommend having a private and honest conversation with your boss. Express your observations about the communication patterns and the use of ChatGPT, emphasizing the importance of transparency in a professional setting. Seek clarity on why this approach is being taken and how it aligns with the company’s goals. Open communication is key, and this discussion can help foster a more transparent and collaborative work environment.


  23. Zzzzzz*

    OK ALL: LW WROTE BACK: They resigned today:

    LW here- this is a case of friends bringing in friends. When I accepted the position, I assumed there was a reason beyond that for his position (which there might be, just one I have yet to experience). I also felt like I might have been being unfair and ageist when I interviewed with the company and had some hesitation about the relative lack of experience. I resigned from this job today when it became apparent that this wouldn’t get any better.

    1. Slow Gin Lizz*

      LW also said in a different comment that they already have a new job too, so HOOOORAY!!!!!! Nice going, LW! I hope you keep tabs on this company and update us on *that* situation in the future because of course we will all be curious how they crash and burn…I mean, if they manage to stay afloat. :-D

  24. Chris Roche*

    If it’s so obvious that you noticed it as quickly as you did, then other people are going to notice it too. ChatGPT has a very particular “voice” when generating outputs, especially when dealing with interpersonal communication in the workplace. That kind of stuff is going to catch up to him really quickly, and put him in a position where he has no business “not taking feedback well” so honestly just sit back, coast along with your own stuff, and wait for the fireworks to begin.

  25. Saturday*

    LW says in the update that the boss and CEO are old friends, which probably explains how the boss ended up in this role. But it makes me wonder… why would anyone want a job that they’re so woefully unqualified for? It sounds super stressful.

    1. Observer*

      It sure does sound stressful. Which explains the really bad “coping” mechanism he’s using.

      1. Saturday*

        I suppose… but not having to feel like an incompetent fool everyday is worth a lot to me too.

    2. Falling Diphthong*

      There’s an anecdote from one of the people involved in FyreFest early on, where they had a meeting in which the people on the ground said “Nothing is happening!!!” and the people in the suite in NYC said “But what if we pulled it all off? We’d be heroes.” (This person promptly quit, because they could see where this is going.)

      It’s easy for people with little practical experience to believe that this will play out like a film montage. See also crypto.

  26. Captain dddd-cccc-ddWdd*

    Boss is clearly out of his depth and over-promoted. He is earning a pretty penny (startup, OP is already fairly senior, and boss is a level above that, and is not a founder of the startup which wasn’t explicitly stated but is clear from the details in the letter) – and totally incompetent. Far from owing it to the boss to tip him off, OP owes it to the company, the founders and their other colleagues to get action taken about this guy before he derails the company into the ground with strange strategy shifts (or AI-generated emails to outside parties, etc).

    I wouldn’t approach the boss with this even if they were more approachable, because what would you say? “I noticed you are so incompetent that you’re getting AI to generate all your work for you and then not applying any critical thinking to it — you might want to be incompetent a bit more discreetly”.

    Startups, unlike bigger companies perhaps, have little room for “extraneous” elements like this guy.

    1. lw*

      OP here- Yes, this is all true. It was almost immediately apparent to me that my boss was in way over his head and felt pressure to be right, know everything, etc. As frustrating as it was in some ways, I felt bad for him because that’s just an awful way to feel daily. I certainly have a lot to learn myself, and I’ve been fortunate to have patient and kind leaders who went out of their way to help me grow. I wanted to pay it forward here, I think this company has a real shot if leadership can right their course. But, you know, people have to want your input! Beyond this bit of behavior, there were a lot of fundamental leadership philosophy and approach mismatches, so it’s possible that my feedback wouldn’t work for him, even if I believe he needs it. I forget that part sometimes. So, this has been a good lesson for me.

  27. Looper*

    You can’t coach someone out of being an incompetent liar. This is one of a long history of cases where an unqualified person full of their own hot air convinces another unqualified person to give them (someone else’s) money to start a company which they will run into the ground due to the aforementioned incompetence. Until start up culture fundamentally changes, this will continue to happen with or without chatbots. Ultimately the decision to stay is based on whether or not that’s something you can deal with (and possibly exploit to your advantage).

  28. Colorado*

    Oh my gosh – this makes me feel so old. I’m 30 years into my professional engineering based job and the only thought that came to mind is “do you want to play a game?…” in a very poor automated voice :P

    I’d have to run.

  29. Dancin Fool*

    I would be concerned about the circumstances that allowed someone who has no idea how to do the job to get hired. Did he chatgpt his way through the interview process? How on earth did someone so unqualified manage to get past the checks and balances of the hiring process? I think it says a lot about how the company and its higher ups are conducting business which would make me want to run for the hills!

    1. DameB*

      Yeah, this is my question. This kid, fresh faced out of college without any apparent skills in management or communications, is a leader at the company? (I presume he’s a buddy/funder of the bro who started the start up?) I wouldn’t want to work in a company that was being run by someone who would hire this dude and put him in charge.

    2. Retired Vulcan Raises 1 Grey Eyebrow*

      I wonder if his qualifications and references consisted of being related to someone highup, or belonging to their social network.
      Otherwise, must have had an extraordinary gullible HM

      1. Retired Vulcan Raises 1 Grey Eyebrow*

        oh, I see that the OP has now commented he is indeed a chum of TPTB

  30. Jojo*

    Now I’m wondering if worst boss of the year will now need to be broken into two categories; Human Bosses and Robot Bosses.

    1. Other Alice*

      If we nominate this boss, does ChatGPT also get a honorary nomination? If argue yes because
      1) their communication did not display effective leadership, and also
      2) for fun.

      1. Naomi*

        I want to say yes because it would be hilarious, and ChatGPT was arguably functioning as the boss here more than the human boss was. On the other hand, at least ChatGPT wasn’t outsourcing the work, so it was more a garden-variety incompetent boss than a Worst Boss of the Year qualifier in its own right.

  31. el l*

    As with a previous ChatGPT question:

    The use of ChatGPT is not itself a problem – it’s a tool. No less, no more. The problem is that the user is not adding any value beyond whatever the tool spits out. Its output is not understood, modified, checked for relevance to the situation at hand, communicated concisely to divergent stakeholders, and so on. Power aside, it’s no different from an intern outsourcing their job to it.

    So on that note of power: All depends on what relationships you have with leadership. If you have a good relationship with someone up the string, I’d put together a packet which shows ~5 examples of where manager’s decision corresponds word-for-word to ChatGPT prompts. And frame it as, “I’m concerned that decision making and other executive responsibilities are effectively being outsourced without your knowledge. Also, that basic professional value-added is not being shown.”

    If you don’t have that relationship, though, leave.

  32. ChatGPT*

    I’m not sure how to feel about this letter. But I will look through my logs and see what I can find.

  33. Record Scratch*

    I’m going to write down and periodically review: “You’re not responsible for saving him from himself, and especially not when there’s a decent chance it would come at a cost to you.”

    Such great wisdom perfectly succinct.

  34. Ally McBeal*

    I gotta ask… why would anyone take a role at a company where the founder/CEO is fresh out of college and this is his first job? I know some people really love the vibe of startups but this would be several bridges too far for me.

    1. lw*

      OP here- that wasn’t shared or apparent in the interview process. I knew he looked young, but you know, you can’t really ask about that kind of thing in an interview. His LinkedIn was super confusing, I now see that it’s absolutely obscuring his actual experience intentionally. I focused on understanding the business model, performance, and goals. About a week or two in, he said, “I used my senior picture for my headshot,” and my soul left my body a little bit. At the start of my career, I worked with a VC firm, and it was essentially all young guys in C-level positions, but the smart ones brought in seasoned folks and listened to them. I figured it was worth seeing if that was the case, the interview process was fine if fast, and I like the product and market. I’d do it again.

      1. Ally McBeal*

        Oof. I feel like I would just start looking elsewhere at this point. You’re not going to learn much (if anything) from him, and he’s probably going to take credit for your ideas and/or stir up problems when he decides that his “fresh” ideas conflict with your seasoned advice.

    2. econobiker*

      Is ground floor entry to get equity in a low valued start up that could eventually POP! making you millions of dollars a good reason?

      Or what if you are frat bros with the wealthy founder(s)? Get a huge resume bump early on as “Vice President of Market Strategy” so that you never again get another job at less than VP level and salary.

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