my coworker passes me messages “from the CEO” … that I think are really from her

by Alison Green on February 15, 2022

A reader writes:

I’ve worked for an 80-person organization for two years in an outward-facing, sales-like role. I come with 20+ years experience. The organization has one HR employee coordinating interviews, terminations, and benefits paperwork. Most of my colleagues work in roles that require casual clothing (a branded t-shirt and jeans). My role, however, requires business suits and dress shoes.

I work directly for the CEO, who is mostly lassiez-faire, but with occasional bouts of exuberance that seem to end in terminations. My boss seems pleased with my work; we’ve never been chummy. About six months into the job, I brought up an issue concerning colleagues outside my chain of command. That started an immediate barrage of emails and pronouncements from the CEO, which included my name as the “accuser.” I quickly learned to not ask for that kind of help from the CEO.

My challenge is with my boss’s assistant, “Elaine.” Elaine texts and calls me at ungodly hours of the morning to alert me: “as per CEO, there is snow and so please wear appropriate shoes” and “as per CEO, please wear a skirt below your knee when meeting with staff” and “as per CEO, plan to wear a higher neckline tomorrow.” These pronouncements happen about every 2-3 weeks, and I’m almost certain they do not originate from the CEO.

The reasons I believe that: First, several of these messages have come while the CEO is out (once while on vacation, two while on bereavement, and another while out caring for a sick relative). Two, the CEO keeps strict boundaries between work and home, and is largely unreachable when out of the office. I’ve never received a text or email from him before 9:30 am or after 6 pm. All of these “as per the CEO” messages have come around 4:30 or 5:00 am. Three, the CEO has no filter about calling out problems with me or other staff. I was in a meeting recently where he opened my office window to (loudly) chastise a staff member for wearing tight yoga pants.

(And lest you think I’m not following guidelines: I think that the nuns from my childhood would approve of my wardrobe, but it can be hard to sanitize my cleavage without a turtleneck and ace bandage.)

How do I navigate this? Again, I think this is from the assistant, not the CEO. I feel stuck that I can’t bring this to my boss (for fear of being painted as a tattle again) or the HR rep (unempowered), nor directly with Elaine (a consequence that would either make my job difficult or gone).

This is weird! If your theory is right that these pronouncements are coming from Elaine and not the CEO, why is Elaine so invested in controlling what you wear — and why, for the love of god, is she texting and calling you at 4:30 am to relay these edicts?! (And why does she care so much about making sure you wear shoes appropriate for the snow?! You are not a child and she is not your mother.) It’s incredibly odd.

Do you know if other people are getting similar texts and calls from her? If you don’t, it would be interesting to ask around and find out.

But unfortunately, you have taken the three main methods of addressing this off the table! Ideally you’d be able to just ask the CEO what’s going on — as in, “I keep getting early morning texts and calls from Elaine saying she has requests from you about what I wear to work, including my shoes and my neckline. Do you have concerns about my work attire that we could discuss directly?”

Or, if you were willing to address it with Elaine herself, you could say to her (in-person, not via a text response — let’s put her on the spot and make her account for this), “What exactly did Rupert say about my neckline? I want to make sure I know exactly what his concern is.” … followed by, “And those were Rupert’s words?” … and maybe, “It sounds like I should talk with him directly since my understanding is that my clothes are squarely within our dress code. Could you get me some time on his calendar for that?”

But if you’re not willing to address it with either of them and HR is disempowered … well, you don’t have a lot of remaining options! You can and should probably block Elaine’s calls and texts, at least outside of business hours, or at least tell her directly that she’s contacting you too early and to wait until (whatever time you choose). Beyond that, all that’s really left is choosing to simply ignore her decrees and possibly post them all on a Things Elaine Says Twitter account, which I would happily read.

But I would really interrogate yourself about the three options that you feel are off the table — particularly speaking to the CEO directly. Yes, it sounds like you can’t trust him to keep the conversation to himself, but that’s not necessarily a problem. In fact, to address this, he would need to tell Elaine you told him about it. The question is really how he’d handle blowback from Elaine and any attempts she made at retaliating against you. If you don’t trust him to handle that well and it would cause you more misery than it’s worth, then there’s no point in doing it — but really make sure that’s true before you rule it out.

Read an update to this letter here. 

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{ 346 comments }

{ 346 comments… read them below }

  1. ecnaseener*

    I definitely think asking the CEO about this can be done without it sounding like an accusation. Even with his hair-trigger reactions. Just act like you believe he said these things: “Elaine said you asked for me to wear longer skirts, could you clarify what length you wanted?” Don’t hint at any suspicions that Elaine is lying.

    1. Dust Bunny*

      Second all of this, but also . . . this sounds like the monkey house at the zoo, LW. I hope the rest of your organization is more reasonable!

      2. Elizabeth West*

        Oh my gaw, yes. I guess the OP is content to stay there, but I feel like this place would drive me bonkers (and right into a different job).

    2. The Cosmic Avenger*

      I wouldn’t even mention Elaine, I’d ask for a clarification about it, like “So when you said above the knee in your email, did you mean while sitting, or just while standing?” That way you’re not even hinting at an accusation, but if he didn’t send it, it’ll be immediately obvious.

      If the OP is really sure it is Elaine sending these, she could always just ignore them, and force Elaine’s hand. If Elaine tried to fake a disciplinary action, that would probably require a meeting with the CEO anyway, in which case the OP could ask for clarification on the request as above.

        1. Momma Bear*

          Agreed.

          Also, I would keep my phone on do not disturb except for specific people. If I get a 5 AM phone call, someone better be dead.

              1. Momma Bear*

                That, too.

                Unfortunately I had the experience last year of a relative passing away and getting a very early call about it. I had anticipated that call, though, and left my phone on.

          2. Loulou*

            Yeah, I have not had the “woken up by a message in the middle of the night” experience since my landline days and cannot understand people who keep their phones on ring all night! I get emails pretty much continuously and would never sleep.

            1. Zan Shin*

              Many of us who live in western states where wildfires can move swiftly on overnight winds never turn our phones off.

              1. generic_username*

                You can put your phone on Do Not Disturb while still getting emergency messages. You can even set particular contacts as able to bypass the DND. I do it every night between midnight and 8:30am. If someone calls me twice in a row, it’ll come through, but otherwise, my texts and calls don’t ring through.

                1. lazuli*

                  That doesn’t work for texts, which is how my county in California is choosing to send emergency alerts. At least it doesn’t work on my phone. They don’t resend the text. (Half the time I don’t get any emergency texts that I’m supposed to get.)

                  I did finally turn all the other non-call non-text alerts off, as friends in other time zones kept waking me up with FB messages.

                2. Kal*

                  @lazuli

                  Depending on your phone’s OS, you may still be able to set something up. I use Android, and both my old phone on Android 7 and my new one on 11 have the option to set up starred/favorite contacts. I set my partner as one, and then set my Do Not Disturb settings to allow texts and calls through from starred contacts but not any others, so that I can get text noises from them but not be woken by spam texts and robocalls.

                  So if the emergency alerts are sent from the same number of set of numbers, you could set up a contact for it and set up a similar system. I’ve heard from some friends who use iPhones that you can do similar things on them, but I’m not sure which versions of the OS or how to go about it since I haven’t used them myself.

                3. Michelle*

                  I had mine set like this, but then if my phone rings in the middle of the night, my sleep -addled brain goes, “It’s ok, it won’t really come through unless they call a second time,” completely forgetting that if I’m hearing it ring that must BE the second time! And since I have teen/young adult kids who may have middle of the night emergencies, that doesn’t work for me.

            2. Curmudgeon in California*

              I work for an East Cost company, but I am on the West Coast. My workplace Slack starts getting @group messages at 5 am my time. I had had it on my laptop near my bedside, as well as my phone. After the third time of getting pinged at 5:30 am, I took it off my laptop and put a DND for those messages on my phone.

              In general, I don’t allow noisy notifications on my phone unless they are literally things I have to act on right then. Notifications of deliveries? Yes, we have porch pirates. Notifications of sales? No. Notifications from games? Hard no. Notifications from social media? Hell no. Notifications from web sites, on any machine? Also a very, very hard NO.

              In general, organizations that want to pop up notifications all the time are as irritating as a random firecracker going off for no reason. Most people I know are not FOMO notification junkies – we have lives that are not wrapped up in what some social media thinks important.

              1. kitryan*

                The thing that bugs the heck out of me is when you have a service where you want notifications on the status of orders/requests, so you can’t turn them off for the app, but it will also send you marketing notifications at all hours. For me this is Uber, Seamless, and to a lesser degree, Fresh Direct. If I am actually placing an order, I want the notification, but I don’t want to know that it’s game day and I could get a platter of hot wings for 20% off!!!!!
                I’m 1 alert from turning Uber’s off all together, and just turning them back on if I need to, since I was only using them for one specific reoccurring appointment that I couldn’t get to w/public transit and I no longer have that scheduled.

                1. Koalafied*

                  You may be thrilled to learn the latest version of Android now allows you to turn off some types notifications for an app and leave others enabled. You can access these options from Settings > Notifications > App settings > [app name] or by long-pressing on a notification in your pull-down shade. It’s been a total game changer for me.

          3. Nina*

            I have a room in my house that, due to a quirk of architecture, functions as a Faraday cage. My phone lives in there from 6 pm to 6 am. It’s great.

          4. Flower necklace*

            At my workplace, we start at 7:30 and coverage is essential. If someone in my department isn’t going to be in, I need to know ASAP so that I can arrange coverage, prep materials, etc., in addition to the thousand other things I do in the morning.

            I have still never gotten a 5 a.m. text. I think the earliest was somewhere around 5:30 or 6, but at least I’m awake by then.

      2. Dust Bunny*

        “I was already planning to wear duck boots. Are the adequate or did you have something else in mind?”

        Like, who on Earth doesn’t know what shoes to wear in the snow?

        1. MusicWithRocksIn*

          I mean, there’s always that one guy who is still wearing flip flops in a foot of snow, but generally not at the office.

          1. Dust Bunny*

            Yeah, but that doesn’t mean he doesn’t know better. I went to college–in the Midwestern United States, where they definitely get winter–with a guy who wore flip-flops and shorts in all weather, snow included. But he knew it wasn’t conventional, he just didn’t care.

            1. tessa*

              Yep. For whatever their reasons, some people can’t accept the reality that summer is over, and the Elaines of the world need to mind their own beezwax about it.

            2. Texan In Exile*

              I keep expecting to see the streets of Milwaukee littered with the corpses of dead, short-clad high school students.

            3. Becca Rosselin-Metadi*

              Everyone in my family went to the same Midwestern university-and my sister went to school with the guy from Samoa who wore a sarong and went barefoot all winter. He said he didn’t feel the cold. Snow/ice/below freezing temps and he never got frostbite! I’m not sure if this was the same guy who kicked for the football team and didn’t wear a shoe/boot or not though. All I can say is that if he was comfy, that was all that mattered-and she said he never looked cold or even shivered.

              1. Anonymous4*

                A friend went to school with someone from Finland. From his point of view, it was quite warm and comfy and he didn’t quite see why everyone was bundling up like that. I mean, it wasn’t even below zero yet —

                1. Reluctant Mezzo*

                  “But this is nice!”–commonly said by coatless people just before getting hit. (though since I live at 4200 feet, I have been known to say this myself).

                2. allathian*

                  Below zero C or F? I’m from Finland, and I bundle up. When I was in college, we had an exchange student from Iceland, and he wore shorts and t-shirts whenever it was above 5 C/40 F (counting windchill). At that temperature, I’m wearing leggings/long underwear under my pants/jeans.

                  The guy from Samoa amazes me, though, because he’s presumably used to a tropical climate.

            5. Momma Bear*

              Right.

              If I wear heels in the snow but I’m meeting the office dress code what does anyone need to care? It’s like do you take x route or y route? Doesn’t matter as long as you get there.

              1. Snuck*

                I fell down a steep set of stairs at a train station once on my commute to work, my laptop (in bag) sliding and being damaged.

                I had to agree in the risk assessment not to wear heels to commute. The kicker for this was my heel was half an inch high, and a square solid one. Not any more/less than running shoes almost. The injustice of that one burns. (And I usually wore running shoes and normally walked the few kilometres into the office, it was just this one time I didn’t due to bad weather.)

            6. Chauncy Gardener*

              I live in New England and there was a kid in high school who wore shorts every.single.day for his entire high school career.

              1. Chashka*

                Yup, my kids had a fellow high school classmate who did the same–in Michigan. I felt cold just looking at him, but he was fine.

              2. Anonymous4*

                I know a young man who dreams of moving to New England — or one of the northern Midwestern states. He’s built like a Clydesdale and he just roasts to death in the temperate state where he lives. Shorts and a hoodie is as warmly as he ever dresses.

                1. Autumnheart*

                  His people are waiting in Minnesota. Nobody will blink an eye at shorts and a hoodie until it gets below zero. Even then they’ll just blink.

          2. Crazy Cat Lady*

            I’d probably walk in wearing flip flops just to see the reaction on Elaine’s face. But that would likely end badly – so file that under “things that you would love to do but never will”

          3. Nanani*

            Russians gonna Russian okay (I’ve never known anyone to do this without being at least a little bit Russian)

            1. Verthandi*

              Not Russian, but part Scandinavian. One of the things I like to do after the first snowfall is to walk barefoot outside and leave footprints where other people will see them.

        2. Not Tom, Just Petty*

          I like this one, because it is the most drastic and least likely to be covered in the dress code. If CEO is who I feel he is, he will first try to act like he knows what’s going on.
          “Per your email about my skirt length, what is appropriate?” allows him to roll into, “I think you are an adult who knows how to dress. I shouldn’t have to tell you,” pushing back on OP the issue of the email source.
          But Dust Bunny’s boots, they are not something that CEO is going to have a pat response for, “what are duck boots? Adequate for what?” would allow OP the opening she hopes for.

        3. Just J.*

          Not to derail, but my assumption is that their snow removal team may get there after the first employees do and there may be slip-and-fall liability. I’m in the frozen northeast. Having an uncleared parking lot first thing in the morning is not uncommon. Hence, the ‘if I tell you to wear appropriate shoes’ then I’m warning you to ‘walk across the parking lot at your own risk.’

          1. Just J.*

            Following up on my post, not that this removes the liability, but does explain early morning text messages from overly aggressive admins.

            1. Persephone Mulberry*

              But I, as your coworker, also live and work in [the NE] and am already aware that I cleared parking lots are hazardous and don’t need to be lectured on footwear.

              If the parking lot not being cleared IS out of the ordinary, then a head up message makes sense, but also, say that. then say that. “The snow removal people are behind schedule today and the lot won’t be cleared before 8, you may want to choose your footwear accordingly.”

              2. Texan In Exile*

                To this point – does admin not wear snow boots to work and then change to Good Shoes once she’s at her desk?

                The only place I have ever seen women wearing Good Shoes in the snow is on The Good Wife, a part of the show – along with her pretty, light winter coats – makes me think that nobody involved in producing that show has ever been to Chicago in the winter.

              3. Sea Anemone*

                “But I, as your coworker, also live and work in [the NE] and am already aware that I cleared parking lots are hazardous and don’t need to be lectured on footwear.”

                And yet, my employer still sends out safety messages about walking on icy surfaces bc even people in the frozen Northeast slip and fall and my employer prefers that they not.

                3. somanyquestions*

                  Right, but likely not at 5 am, and also likely not as an admonishment to wear proper boots this time.

                  A normal message is to please be careful in the lot. My last employer used to tell everyone to penguin walk for stability. :)

            1. Gustav*

              ooh, I’m fascinated by the gender discrimination aspect here: Is the CEO warning Bob from accounting not to wear such tight pants? are there equivilent discussions happening with the male employees about their clothing?

          4. Lenora Rose*

            I’m in the very frozen north, and we have had a LOT of snow this year, as well as a lot of ice, and across the city, slips and falls have been up, including ones requiring hospitalization (which last part made the news).

            This early morning admin message still seems bonkers, especially if sent to a single person, and especially if “Per the CEO” in this case was a lie. This is not how you write “Watch out for unplowed parking lots!”

            (I absently wrote “untamed” for unplowed. There’s a vision…)

          5. Jaydee*

            But this seems like the type of thing that would go out in an all-staff email a few days before the first expected snowstorm of the season. “It’s that time of year again when snow makes everything simultaneously beautiful and miserable. Please remember that the crew that clears our parking lot and sidewalks often doesn’t come until after 6am and areas may not be cleared of snow and ice yet when you arrive. Wear good footwear. Walk carefully. Take heed and govern yourselves accordingly.”

        4. jm*

          see, i interpreted that as “it’s boot weather outside, so make sure you bring heels/whatever to wear in the office”. like reminding op the rules still apply even during a blizzard.

          1. Just J.*

            I can see this as I have really comfy duck boots that I will just wear all day on snow days (which means I track in all the snow and crud from our unplowed parking lot).

            1. Lexi Lynn*

              I worked with a woman who always wore boots when the weather was bad. Of course those boots usually had stilletto heels. Over the years there were broken bones, but she’s an adult and of stillettos in the snow makes her happy, no concern of mine.

          2. somanyquestions*

            Which is kind of saying they think she’s an idiot. That’s not a normal thing for a co-worker to remind a grown up human about.

          4. Old School HTML*

            When trying to figure out how to dress in an office enviro (new job in fall 2018), it appeared everyone wore low, flat, black ankle boots from fall through spring. Mine were sturdy enough for snow (and I use YaxTrax on ice), but apparently appropriate for this office. (Gov’t agency.) I’m in Maryland, where we’ve been going between 60+ degrees and snow, every few days this past week: our snow is rarely deep, but our weather patterns are variable and apparently a supreme challenge for forecasters.

            1. Birdie*

              I’ve never lived in a place where weather forecasting was as tricky as in the Baltimore/Washington region. Will it be 10 inches of snow or 65 and sunny tomorrow? No idea! We’ll all find out tomorrow on real time.

        5. CB212*

          I kind of read that as “we know you’ll be in snow boots on the commute, so please make sure you’re wearing pumps in the office”

          1. NotRealAnonForThis*

            Similar reading…I think I was reading it as more “Elaine is trying to police the LW’s wardrobe for I can’t quite place the reasons”.

            1. Curmudgeon in California*

              Yeah, that’s how I read it – Elaine trying to police her wardrobe for reasons that the OP doesn’t understand either. IMO, Elaine needs to stay in her own lane.

        6. Batgirl*

          Ooohhh. I would be so tempted to do a lot of follow up questions, to an annoying degree, with pictures. I get that not everyone has that kind of energy for pettiness, but this is the kind of thing were I will happily draw my sword.

        7. AnnieG*

          Given that Elaine has commented on skirt length and necklines, I’d bet she also thinks the letter writer wears “sexy” shoes (open toe/strappy) and is using the snow as an excuse to tell her to wear more conservative ones.

        8. KoiFeeder*

          I had never heard them called duck boots before (my family just calls them snow boots) and that resulted in a very, very entertaining mental image while I googled that one.

          Fortunately, it turns out the makers of children’s boots have already seen my logic. Unfortunately, I have giant clompers and no hope of squishing them into duckie duck boots.

      3. Sparkles McFadden*

        Yes, leave Elaine out of this entirely. I think it’s best to deal with everything at work as if people are telling the absolute truth, even when you are sure they’re not.

        So, in this case, you’d approach the CEO and say “Would you please be more precise about the issue you had with what I was wearing on January 11th when I met with out client reps from the Acme Corporation? I just want to be sure I understand the issue moving forward.” The CEO will say “What?” and then you get to show him the goofy text threads. Then it becomes the CEO’s issue. Elaine might still send crazy stuff, but you get to block her during non-work hours.

        Your only other choice is to just ignore it.

      4. MCMonkeyBean*

        Yeah, I feel like I would address it by acting as though you do assume the messages are really from him and then if he is like “what on earth are you talking about?” you can clarify about the messages. I feel like that would come across differently than “tattling” (which is of course not at all what you would be doing by bringing this up, but if you think that is how he would interpret a more direct approach then this seems like a way around that).

      5. doreen*

        I think the messages are coming directly from “Elaine” and she is prefacing them with “as per the CEO” , so leaving “Elaine” out of it won’t work. I think “Elaine said you asked for me to wear longer skirts, could you clarify what length you wanted?” would work – and I think it’s unlikely that the OP will be painted as a tattle. It’s way more likely the CEO will be annoyed at “Elaine” for borrowing his authority inappropriately if that’s what’s happening and if the messages really do original with the CEO , there isn’t anything to tattle about.

        1. ecnaseener*

          Yes, but people are saying you don’t need to mention her up front — you could just say “I got your message this morning about my skirt” and if he did ask Elaine to relay that message he will know what you’re talking about. Either way works.

      6. Zephy*

        My read on it was that Elaine was calling/texting the OP at bizarre hours, as herself, but saying in her message that “per CEO, do xyz” – not that the missives looked like they were coming from the CEO.

      7. KuklaRed*

        I think the OP knows that Elaine is sending these – they are coming from her number. What is being questioned is that the “requests” are not really coming from the CEO – Elaine is writing them “as per CEO” so she can pretend that her orders have some heft to them. The whole thing is ridiculous, but this wouldn’t be the first time that a CEO’s assistant started acting like they had the same influence as their boss.

        1. Who Plays Backgammon?*

          Yeah, those admins. They just about run the place except that they don’t. This is one to remember on Admin Day. That’s snarky, I suppose, but there are always those comments about the influence and power that admins have–but it’s actually their boss’s.

      8. Despachito*

        I WOULD mention Elaine, but in passing, just as ecnaseener is suggesting.

        If I don’t, it may not land the way I want it to land.

      9. Chauncy Gardener*

        I like your first paragraph’s approach a lot.

        I would also REALLY like an update on this!

      10. commonsensesometimesmakessense*

        I would mention Elaine actually. But nonchalantly, as suggested by ecnaseener. That way if it is coming from boss, there is no suggestion that OP is pointing fingers, but if it is not coming from him, he is aware of a potential issue.

        I see that it could blow up in the sense that he could scold Elaine and Elaine could get mad at OP. But even if boss acts surprised and says he has no concerns, OP would not be wise to just ignore messages from Elaine (which will annoy Elaine anyhow, plus, not every message she says is from the boss is going to not actually be from the boss). Also, if boss is really surprised by OP bringing this up, he is likely to ask anyhow.

    3. Office Lobster DJ*

      This. I’d even be tempted to do it in e-mail, copying boss and Elaine. Control the narrative from the start, eliminating the possibility of anyone twisting your words, and at the very least you can’t be painted as a sneaking tattletale. (Of course, OP is the only judge of whether that would work in this office)

      Also, this is wild and I want that Twitter account.

      And block and ignore Elaine.

      2. lex talionis*

        And really, who cares if you are painted as a tattletale in this instance? If she is lying regarding communication from your boss she should be called out. Who knows, maybe she is doing this to others?

    4. Smithy*

      Agree on this – when it comes to skirt length and appropriate shoes – asking for clarification doesn’t have to be an accusation or a bad thing. Particularly as your dress code is already somewhat different from most staff are wearing.

    5. animaniactoo*

      That’s a way to go. Another one would be:

      “I’ve gotten the impression that there are some concerns about the way I’m dressing, is this a concern that you have? Do you think there’s an issue?”

      You don’t need to say where you’ve gotten the impression.

      1. ecnaseener*

        I disagree, I think that sounds very transparently like the speaker waiting to be asked what/who gave them that impression. (And then they say “oh, Elaine directly told me so” – admitting they didn’t just get a vague impression, they were told, now they look even more transparent.)

        With what we know of this CEO, the LW wants to avoid any whiff of tattling.

        1. animaniactoo*

          Nah, because LW can deflect that with “it’s a couple of comments I’ve gotten, I don’t want to really go into it further but wanted to check that I’m not missing something.”

            1. Anonymous4*

              But the next time Elaine sends her a “the CEO says — ” e-mail, she can send the devastating response: “I’m afraid there must be a little misunderstanding. I asked the CEO what skirt length he preferred I wear, and he didn’t have any issues with my skirts. Before I make any changes, I’ll wait until he e-mails me himself to express dissatisfaction with my work wardrobe. Thanks for understanding!”

    6. JSPA*

      “Hi Jim, Having received several very early morning calls about my clothing, I’m wondering if we need to revisit the dress code for my position. Can we do that during normal working hours? 4:30 AM is a disruptive time to receive non-emergency messages. I don’t want to have to block Elaine from calling or texting me before 6 am, in case there’s an actual emergency, but neither am I willing to take work calls about my clothing at 5 AM.”

      2. NeutralJanet*

        I like this because even if this is a genuine problem—that is, even if the CEO really does feel that OP is dressing inappropriately and really is telling Elaine to talk to her about it—it’s weird, unnecessary, and intrusive for Elaine to call at 4 AM to say that OP shouldn’t wear a low neckline.

        1. Aggretsuko*

          Apparently Elaine wants to give OP PLENTY of time to rethink her wardrobe before going into the office. I guess that’s the 4 a.m. logic, but seriously?!?

    7. TinaTurner*

      Can’t the texts be printed out or forwarded to Boss? So he actually sees them? And to HR?
      Say you want to verify they’re “per” him because they seem very odd and you’ve also gotten phone calls from the asst. at odd times.

      1. ecnaseener*

        They could, but from the letter we know the CEO hates anything approaching tattling. That’s why I think the best way to proceed is to bring it up innocently and let him discover the issue himself.

    8. Don't be long-suffering*

      I would just ask the CEO what his concerns are about your clothing, without mentioning Elaine. If he doesn’t have an answer, ask about your shoes, your neckline, etc. Ask about the specific thing in today’s text, every time it happens.
      If he has no problem each time, then the convo can turn to Elaine.

      1. Amaranth*

        I think LW has to be clear that she feels she is responding to his concerns, rather than CEO wondering why she is asking him to look at her skirt length and neckline. Without context, it would start seeming that she either has no confidence in being able to dress herself, or that she wants him to look.

    9. Mina, The Company Prom Queen*

      This! If you take this approach, Elaine will have egg in her face if the CEO didn’t say the things Elaine said he did. You can even put it in a way that you’re concerned that you may have done something wrong and want to make sure you aren’t breaking any rules.
      And once you have your answer, which is probably that Elaine is the culprit here, you can just ignore her unless something is truly relevant.

      Elaine sounds worse than Self-Appointed Hall Monitor I worked with at my last job before my current one. Why do some people have the need to boss their peers around? Who has time??

      Anyway, good luck with this.

    10. PB Bunny Watson*

      This! Or, “I understand you have concerns about my neckline, and I was wondering… did a client complain?”

    11. Amethystmoon*

      It’s very strange since many of these suggestions seem like they would only apply to women and not men. Is this a public-facing job? Does the company have a dress code that has not been updated since the 1980s? Also considering snow, I’d wear boots but then change to shoes once I get to work. It wouldn’t be appropriate to wear anything other than boots from the parking lot in due to ice. That’s what people used to do anyway, in the upper Midwest, in the days before COVID when you had to go into the office.

    12. TootsNYC*

      Also include the information that she texted you at home at some weird hour of the morning. Don’t label it weird; just say “Elaine texted me this morning at 6 AM to tell me that you said you wanted me to wear longer skirts. Could I check with you about skirt length?”

    13. Liu1845*

      I would be so fed up with this. I would start forwarding her emails to CEO and asking “Exactly where would you like my skirts to stop at?” “Why do you think I need to be told to wear weather appropriate footwear?” “What do you consider an inappropriate neckline?”. Hit forward, add CEO on the “TO:” line, & move assistant to the “CC:” line. You aren’t tattling, you are asking for clarification.
      Channeling a “mean girl”, vibe I would also ask why it was necessary to send me this at 4:30 am (or whatever shows on the email). The CEO needs to know she is using his/her name for petty power trips. What else has she done in CEO’s name?

    14. C*

      My theory: CEO is having an affair with Elaine. He goes home from hanging out with her at 3/4am (after the bars close, perhaps?) and has mentioned the clothing requests to her over the course of the evening, so she texts/calls you about it then. Probably tells his wife he was super busy at work the whole time.

    15. Cait*

      Please do this and please give us an update. I want to hear the fallout because I’m pretty sure you’re right and Elaine is lying. If I were the CEO I would be livid that my admin is suggesting to employees that I want to police what women wear around the office, esp. if it pertains to their necklines.

    16. Jaydee*

      Since you’ve received multiple of these texts and calls, I think it would absolutely make sense to have a chat with your boss. The chat you would have if you believed these messages were actually coming from him. The chat that honestly and earnestly attempts to clarify the dress code because you want to make sure you’re presenting yourself in a way that best represents the company. Something like: “So Elaine has contacted me in the mornings before work a few times now to relay messages from you about what I should or shouldn’t wear to work that day. I’ve always tried to dress professionally because I know my position is outward-facing and how I present myself reflects on the company. Since it’s happened multiple times now, I just wanted to touch base to make sure my understanding of the dress code is accurate and that we’re on the same page going forward.”

      If your boss is really the one behind these dress code edicts, in theory he should be willing to have this conversation. Maybe awkwardly. He might have passed messages through Elaine because he felt weird talking to you about the length of your skirts or your cleavage I even if he’s comfortable reminding employees that yoga pants aren’t allowed. (Which could easily be true. Especially if that’s a categorical rule, it’s a little less focused on the specific employee’s body versus singling out specific items or cuts of clothing that fit you a certain way because of your figure).

      On the other hand, if these edicts actually come from Elaine and not from him, he’ll probably cut you off pretty quickly and say “What messages? I’ve never had an issue with how you dress, and if I did, I’d tell you. Now what the heck has Elaine been telling you I said?”

    17. Snuck*

      Agree… I call this “blonde ponytail’ – I am referring to my younger years when I had a glorious strawberry blonde ponytail and was very young for my quite senior role… and intentionally played a little perplexed when crazy stuff like this came up. Time to do a casual “Oh, and Elaine has texted me a few times about my shoes, and clothes. Can I just check, is there anything you’d like me to change?” And watch him flounder. He will either know all about it, and know he’s stepped over lines… or he’ll be very confused and say “no you dress fine, I’m not sure what that’s about” and you can smile brightly (and flick that ponytail) and say “oh good, it’s so important to me that we’re all good! Now about this TPS report, I think the numbers here are interesting because…..”

      (It’s a challenge to find the balance between professional, gender based norms and expectations in a male dominated field, and a workplace full of overt sexually inappropriate behaviours – I wasn’t ever going to go the ‘sexy’ route, but needed to not ‘threaten the higher ups’ either. I learnt a LOT there about how to manage perceptions as well as horrid co workers and managers.)

  3. Alex*

    I personally would just tell Elaine that I didn’t need such reminders, and to please take me off the 4am text reminder list. No tone of annoyance, just a simple, “Oops, I’d like to be unsubscribed!” as though what she is doing is perfectly normal.

    Because I have no doubt she is TRYING to get a rise out of you. Why else would she make up these things and text you at 4am? Sounds like someone looking for drama, so don’t play into it.

      2. JSPA*

        This. Especially if she’s somehow set the messages to send at 4:30, and is herself fast asleep. Make her phone ding, every time she makes yours ding.

    2. Office Lobster DJ*

      Not exactly what you suggested, but the joy I just got from picturing OP responding to Elaine’s 4am texts with “Unsubscribe”….

      1. Yorick*

        STOP.

        They usually have you reply “STOP” to unsubscribe, and this is what I will do if I start getting annoying texts.

        1. Hillary*

          I got one recently where they didn’t have Stop to unsubscribe, but Verizon replied to Stop that they vendor wasn’t following rules and they’d now been blocked from texting me.

      2. The OG Sleepless*

        When I was in charge of an event for my son’s Cub Scout troop, I sent an email to a group of parents and one parent sent back UNSUBSCRIBE! (It was definitely the right email address.) I’ve been a little salty about that for 15 years.

    4. Artemesia*

      And absolutely make sure you are not getting alerted at 4 am — silence her notifications — if you can don’t have your phone on near the bed at night. And then ignore the notices.

    5. The Rafters*

      I have a feeling that OP is reasonably attractive and Elaine is jealous. Otherwise, why all of the focus on her clothes, especially since OP says nuns would find her choices acceptable. OP, I would bypass Elaine as far as scheduling a meeting with your CEO, if possible. If you already have a one on one, bring it up to him then.

      1. Loulou*

        I don’t think “jealous” is indicated in the letter, and unfortunately there are all kinds of busybodies out there who are obsessed with what other people wear for reasons other than “she’s pretty and I’m jealous.”

        1. Mallory Janis Ian*

          We had a deans assistant who monitored women’s clothing choices based on whether they were attractive, or heavy, or whatever else triggered one of her Strong Opinions about what certain women should wear.

          Ex. for a staff member who was overweight, she constantly told her that her clothing was too tight and that it was ill-fitting (it wasn’t; the woman was just overweight and was dressed normally). With another staff member who was attractive, she kept admonishing her that she was distracting people by showing too much cleavage (she was not showing an unusual amount of cleavage; she was just attractive so people noticed her regardless). After the deans assistant told her one too many times about her cleavage, this woman shot back, “Well, god gave them to me and I’m going to use them!” Everyone laughed, and it shut the deans assistant up about it — not that I’m advising this for the OP! It was just funny when it happened at my office.

      2. Batgirl*

        It’s super common for women with big boobs to be clothes-policed. It’s not necessarily jealousy but a fundamental lack of understanding that you can’t cover large chests like you can small. It simply attracts even more attention to them! It’s only slightly more weird that its branched out into shoes/hemlines etc, because Elaine has her red pen out already and there is a certain type of over empowered, under managed employee who is power hungry, bossy and never gets taken to task for being a busy body.

    6. Seeking Second Childhood*

      I’d extend my “do not disturb” night time settings until (normal start time – 10 minutes).
      And I’d seriously think about forwarding the text messages to the CEO’s email. But…that might not be wise.

      1. Seeking Second Childhood*

        And one of Alison’s classics gets replied to Elaine the next time she mentions cleavage: “Please stop commenting on my body.”
        I like the description of your neckline being something the nuns would approve of.

      2. Ashley*

        I agree on DND. I would set Elaine messages not notify me unless I had to get her texts and then it would be an hour setting so it was during work hours.

        1. Chlorite*

          This part! If the CEO doesn’t message before 9:30 or after 6, I would have Elaine set to DND from 5:45 pm to 9:45 am! And it doesn’t sound like her “as per…” messages are terminated with a question mark so could OP just…ignore and never respond?

      1. JSPA*

        Yeah, there’s that, too. If someone’s violating the dress code, you remind them of the dress code. You don’t yell about what’s covering their ass, out the window.

      3. Batgirl*

        That detail really seems to support the idea that the CEO would over correct people’s dress in the worst way possible. Just because they “have no filter” doesn’t mean they won’t outsource messages at anti social hours

      4. Marthooh*

        Also not normal throw tantrums–um, I mean, “occasional bouts of exuberance that seem to end in terminations.”

    3. Anonymous Hippo*

      If my boss yelled out the window at me anything other than “watch out for the giant hole you are about to walk into” or similar I’d be gone. I can’t imagine continuing working in an atmosphere. Heck, I grew up basically in a cult and we weren’t this controlling.

    4. alannaofdoom*

      Yeah, I feel like this letter buried the lede… a company where the CEO *interrupts a meeting* and opens the window to *publicly yell at an employee for her attire* is not somewhere I’d want to work! OP, it’s by no means an emergency but, you know, it’s a job seeker’s market right now. Get out while the getting’s good!

      1. Curmudgeon in California*

        And Elaine seems to be taking the lead on policing people’s wardrobe from him. I would be looking for another job.

        I had to work in a “dress up” environment *once*, as a temp. I spent most of what I made over room and board on clothes. A huge waste of money just so I could look “business professional” for an in-house, no client contact role. Not interested in doing that ever again.

  5. Gnome*

    I think this could be raised without accusation. Just something like, “Oh, Elaine messaged me this morning to tell me about your request for X. I thought it was a bit odd since you usually tell me things directly. Should I be coordinating these things with her going forward?” Or some other question you would ask if the comments were totally appropriate. Just imagine she’d said something totally bland like, “per CEO please remember to print the fliers on blue paper” and you’re not sure how Elaine fits into this.

    1. DANGER: Gumption Ahead*

      Or text the CEO later that morning with pictures of 2 pairs of boots asking, “Elaine texted me and said you wanted me to wear appropriate winter footwear. Which do you think is better?”

    2. Despachito*

      Exactly so!

      I think the key thing here is to make it sound like you genuinely believe that Elaine was indeed conveying CEO’s concerns (who knows? he may think such a comment is more appropriate if coming from a woman).

      If she indeed did, you have nothing to lose. If she invented it, she may be in trouble, with you as an innocent bystander.

  6. Anononon*

    I think Alison is right to push back on OP’s convictions that she cannot take any of the three ideal solutions/paths. Because, otherwise, there literally is no way to handle this beyond just ignoring the messages/calls. Which, honestly, doesn’t sound like the worst idea? I am just curious, though, what advice OP was looking for, unless she was just looking for confirmation that this is nuts and beyond weird. (Which, it is! You are justified, OP!)

    1. Threeve*

      If you rule out talking to everyone relevant (CEO, HR, Elaine) there really aren’t any reasonable options.

      So…hire a private investigator to catch Elaine in the act. Or get a doctor to explain that you have Don’t Talk About My Clothes Disease. Call her back and just start sobbing really loudly about how sorry you are about your cleavage.

    2. Not Tom, Just Petty*

      I agree, because I support blocking/silencing/ignoring 4 am posts (from anyone!) but what if this chowderhead forgets and texts something you actually need to know? I’m picturing like those people who post on a fake IG account:
      @Notes from the CEO and then forget to switch to their real accounts before responding.
      Better to put it to the CEO someway, just to get it out there. Even if it’s, “Can you ask Elaine to send your text messages after 7? 4 am is disrupting my household. I don’t want to silence her but I can’t wake up the whole house every week.”

      1. Amaranth*

        I don’t feel like anyone should be expected to wake up for ANY text at 4 or 5am. If its an emergency, then the person can call.

    3. Hippo-nony-potomus*

      Given that this is incredibly gendered (wear a skirt below the knees, watch cleavage), I would report it to HR. It doesn’t matter that HR is handling paperwork and not really there for heavy issues of harassment and such; it’s a box that needs to be checked. I’m also going to flag that even though Elaine is a woman, that does not insulate her from acting in a sexist and discriminatory manner.

  7. NYWeasel*

    I’m curious about why you wouldn’t ask the CEO for “clarification” about his requests? If you wrote in saying that these comments were coming from the CEO, I would expect the advice to be along the lines of “Can you explain this more to me, so I understand what you are asking me to do?” If you approach it that way, then you’re covered off on if he actually gave the direction, and if not, well you didn’t throw Elaine under the bus in any way…

    1. I'm just here for the cats*

      I think she’s just afraid of what’s going to happen. Since the last time she brought up a problem with the CEO he went ballistic and sent emails to everyone and named her as the acuser.

      I wonder if this is why elaine is doing these things. A work friend or something got in trouble or fired and she blames the OP so she’s making all of these weird suggestions.

      1. IndustriousLabRat*

        I also read this as Elaine is being retaliatory/bearing a grudge about something regarding the earlier situation, which may mean that this current behavior could be replaced by another small or subtle aggression if this one is put to rest.

      2. Not Tom, Just Petty*

        and, apparently, used the word “accuser.” Geez, save it for treason, or at least sedition there, Supreme Commander of the OP.

    2. Butters*

      I worked for a guy like that CEO. He would find a way to punish you if you displeased him at all and it didn’t take much. I can completely understand why OP doesn’t want to approach him.

  8. Clorinda*

    Reply with email expressing cheerful compliance (“Yes, I do plan to wear shoes today!”) and cc the boss. Do it every time.
    Alternative: Don’t even open the emails, and if Elaine asks, “Goodness, I don’t read emails while I’m getting ready for work.”

    1. Alex*

      Or take it one step further and start texting HER at 3am with your entire wardrobe laid out asking for feedback. Start with a small infraction–a too short skirt, etc., and escalate into the ever more ridiculous. Velour tracksuits. Banana costumes. Diving flippers. Text her at least 20 times a morning.

      Ok don’t actually do that.

      2. MissBaudelaire*

        I mean… I’d appreciate that, at least.

        After all, it’s obviously appropriate to text/call people at stupid o clock for bananas reasons. As per Elaine….

      3. Sola Lingua Bona Lingua Mortua Est*

        Ok don’t actually do that.

        Definitely don’t do that. The odds are too good Elaine would run with it and make things even worse.

      4. tessa*

        >Or take it one step further and start texting HER at 3am with your entire wardrobe laid out asking for feedback.

        *snort*

        1. Anonymous4*

          “Do you think the red flippers look better with my ensemble? Or should I go with the black ones? And the Carmen Miranda hat — more bananas? Or another pineapple?”

    2. Tired social worker*

      Are these emails or texts, though? From the letter it seems like they’re texts, and unfortunately I don’t think there’s a cc option on those. But it is a great idea if possible.

    3. RabbitRabbit*

      Probably easier to put DND on during sleep hours, glance at the texts in the morning to see if there’s anything actually important beyond dress code nonsense, and utterly ignore them otherwise. Replying to the texts/calls just encourages her to continue.

  9. Butterfly Counter*

    I’m guessing the “as per the CEO” phrasing means that the CEO told her about the dress code once or twice and she’s deciding to interpret it and enforce it as she sees fit. She didn’t say WHEN the CEO informed her, she’s just using his power to try to dictate OP’s wardrobe.

    2. Just Your Everyday Crone*

      That was my impression, too, that Elaine has designated herself the CEO’s deputy and acts (over)zealously in making sure all his wishes are everyone else’s commands.

    4. Eat My Squirrel*

      This is what I was thinking. Elaine isn’t saying the CEO just told her just now to remind OP about the dress code. I figured he’d said something once months ago like “hey, Elaine, I’m going to be out next week, make sure OP remembers not to show her cleavage at this big client meeting,” and Elaine made it her solemn duty to become Clothing Police for the office.

    5. AND*

      This is my thought as well, so then Elaine has plausible deniability if OP brings the issue to CEO and he says “I never said that…” and Elaine can say “… at one point he said everyone needs to wear acceptable shoes, and you have not been doing so.”
      I do think OP’s best option is to talk to the CEO, but there’s a risk that this then puts OP’s compliance with the dress code (as interpreted by Elaine) front and center, and could get very messy based on the background of how the company operates

    6. RabidChild*

      Is it just me or is singling out gendered things like skirt length and amount of cleavage incredibly problematic? I’m not saying OP’s CEO is sexist, but Elaine’s missives sure made me think so. Perhaps the whiff of an accusation of sexual harassment will get Elaine to back off? She wouldn’t want him to be accused of that based on her behavior, I am sure.

      1. Eat My Squirrel*

        Of course it is. But if it truly is coming from CEO (and I’m guessing that in some way at least, it is), there’s likely not much one can do about it unless there’s a board of directors or it actually crosses into true harassment territory. It’s harder to prove with this one because OP has a role that requires more professional dress than everyone else. It would be more clearly sexist if it applied to everyone in the office, and it’s not clear from the letter that it does.

        1. Eat My Squirrel*

          *if it applied to all women in the office.
          If it applied to everyone, no problem. I know some men who need to wear higher necklines at times…

    7. TechWorker*

      Yeah and to be honest, it could (being charitable here) be something like the CEO has made it Elaine’s job to check dress codes are being followed, and the ‘as per CEO’ just means ‘CEO wants dress code followed’. Her weird interpretation of the dress code and 4.30am (!?!) texts are another matter. I’m not sure that prefacing it with ‘as per CEO’ necessarily even implies ‘the CEO said this’ rather than ‘this is on CEOs orders’…?

    8. Missy*

      That was where my mind went also. Although because CEO is the type to stop a meeting to freak out about Yoga Pants, it may be that the CEO has empowered her to be the fashion police on his behalf.

      1. Curmudgeon in California*

        Ugh. Just ugh. I would be looking for other work if I was the OP. OTOH, maybe fashion policing is part of her field? But I wouldn’t be able to put up with either the CEO or Elaine.

    9. Kes*

      Am I the only one who thinks given the shouting out the window incident that it is possible that these may actually be from the CEO, who does after all seem a little overly concerned about employee dress, and that whenever he’s not at work (in the window where OP hears directly from him) that he just sends anything he wants done to Elaine which is why they’re all coming from her

      1. PT*

        This is what I also thought. I’ve worked in places where you end up with informal leadership, ex: someone the boss is using as a second in command, but the person’s title does not reflect that, and thus some of the employees are unaware that said person has these duties and are confused as to why their peer is telling them what to do. (When I was in this job I had a man refuse to talk to me because he didn’t like taking “orders” from a younger woman…even though they were mostly things like, “FYI X could get you written up if management sees so please do Y instead.”)

    10. BethDH*

      Yes! I hoped if I scrolled comments far enough someone would have said this. It seems like the most obvious interpretation to me so I thought I must be way off when no one else was saying that above.

  10. I AM Sparkling }:(*

    I wonder if Elaine is jealous of the LW, who gets to wear “special” business clothes instead of jeans and t-shirts like the rest, or insecure about LW’s experience or even having to “share” the CEO with another person.

    2. Observer*

      Yeah. I think that that’s a really good possibility.

      Also, I get the impression that the OP is busty, and I wonder if Elaine has a problem with that and wants the OP to be “less flaunting”.

      /sarc / Because existing with a big bust or curves is EXACTLY the same as flaunting your body, in case that wasn’t clear. / sarc

      1. Keymaster of Gozer (she/her)*

        I’ll put money on there being a large amount of ‘that woman needs to dress to hide her curves, it’s inappropriate to have large system attributes’ in that person’s thinking.

        She’d probably only be satisfied if they rocked up in a neck to floor tent…

      2. MissBaudelaire*

        I have a big problem with dress codes in schools for a myriad of reasons. One of them was that in high school I was banned from wearing anything other than t shirts or sweaters. And no V-neck either. I was ‘too busty’. But other girls who were less blessed in the chest could!

        Sure, let me sit here in eighty degree weather when we don’t have any AC and melt away because a glimpse of my cleavage might cause another student to go crazy. Like I’m some sort of Eldritch horror or something.

        1. DANGER: Gumption Ahead*

          OMG. My next business idea: cleavage tentacles. Just put them on the neckline and voila Eldritch horror covering the offending landscape.

          1. MissBaudelaire*

            “MissBaudelaire, why did Jimmy claw his eyes out after he looked at you?”

            “Tried to look down my shirt, ma’am. What has been seen cannot be unseen.”

        2. I AM Sparkling }:(*

          Well, it’s all your fault for daring to have big boobs and tempting those poor boys who don’t have enough self-control to not obey their hormones. Boys will be boys.

          1. I AM Sparkling }:(*

            I put sarcasm tags in that post, but I think the software ate them. Yes, that was heavy-duty sarcasm.

            1. MissBaudelaire*

              LOL, I knew!

              I guess I should have worn loose fitting turtle necks covered by overalls with shawls so no one could see me.

              Our principle used to run around with a little yellow ruler to measure our shorts/skirts/dresses and to see if we were showing too much cleavage. Like, you have nothing better to do but that? And of course, it was just “But yesterday So and So wore something and SHE wasn’t in trouble!”

              How about no nipples or cracks, now get to class? How about that?

              1. Jaydee*

                “No nipples or cracks, now get to class” is the best educational dress code philosophy I’ve ever seen.

  11. Blisskrieg*

    A lot of this is focused on the origin of the messaging, but I’m more concerned about the hyper policing about the dress code. Constant comments on people” wardrobes–from any corners–is the most bizarre part of this situation. Especially hollering about the yoga pants out the window. Why is so this organization so focused on what people wear? It’s yucky.

    1. Dust Bunny*

      I think part of the point is that the LW is not convinced that the policing is real, and that’s it likely harassment from Elaine that the higher-ups don’t know about.

    2. I AM Sparkling }:(*

      Sh!t flows downhill. If the head honcho is so hung up on people’s clothing that he’ll holler out an open window at someone, others will take their cue from him.

      1. Goldenrod*

        This sounds like the kind of twisted, codependent work culture that I am (unfortunately) familiar with.

        I doubt Elaine is making up this stuff out of whole cloth. My guess is that the CEO gossips/complains about the other workers’ attire, and she is “helpfully” passing it along….although what she is really doing is allowing him to use her as a tool to spread his poison. Not that she’s great either! They both sound awful to me.

        Anyway, Alison is right – just ask the CEO directly. I’m guessing the CEO likes to BOTH directly verbally assault employees AND be passive aggressive. The two are not mutually exclusive. My last boss was like this! But people like that HATE being put on the spot and asked to directly explain themselves.

        1. IndustriousLabRat*

          “what she is really doing is allowing him to use her as a tool to spread his poison. ”

          Or alternately, taking the CEO’s toxicity as carte blanche to play out her own toxic behaviors. Big Bully Boss is a bully. Elaine can safely expect that if she bullies the same person that the Bully Boss already has gone “off” on, there won’t be repercussions. I’m still scratching my head about why she has seemed to latch onto her self-assigned wardrobe policing project so wholesale!

          She could be doing it to:
          -Curry favor with Bully Boss, even knowing on some level that’s she’s being weird/rude
          -Due to an actual grudge against OP
          -Because it makes her feel more powerful
          -For the LOLs, and she’s just mean and enjoys stirring pots
          -Out of complete misinterpretation of what Bully Boss actually wants her to pass along, and she’s aggressively clueless.

          Will we ever know? Probably not, though I’m genuinely curious and hope for an update, especially if it’s LW popping up in Friday Good News with a dream job offer away from the crazy, or Bully Boss and Elaine being transferred, the both of them, to another state.

    3. Karia*

      I don’t think it’s beyond the pale to tell people not to wear sportswear to work. But hollering out of the window? 4am texts and phone calls? Absurd.

      1. Charlotte Lucas*

        Yep. Inappropriate dress does not cancel out inappropriate behavior. Or vice versa

        I know yoga pants are OK for a lot of jobs, but they’re also not OK for many. And it does sound like there’s a dress code.

        1. ThisIsTheHill*

          For all we know, Yoga Pants was running to the gym on their lunch hour or stopping by on a day off. They were outside of the building, after all. It’s fine to enforce the dress code in a professional way (e.g. not any of the ways this company is) but there are a boatload of reasons someone could be wearing something outside of the code at any given time during the day.

    4. I'm just here for the cats*

      How much do you want to bet that this is only focused on women’s bodies and not men’s? I bet if Kyle wore shorts that were above the knee nothing would have been said.

    5. Honey Badger*

      Yeah, this is the part that weirds me out too. Why are these people (CEO or assistant or both) so invested in monitoring what people are wearing?? Not just necklines and skirt lengths and yoga pants – which sounds excessive and (gendered in an icky way…) — but also 4:30 am warnings to wear weather appropriate shoes? S0 strange.

    6. Mockingjay*

      On the boss’s part, concerns about attire could be easily solved with a written dress code: business casual for client facing roles, jeans or twill pants for fabrication or warehouse work, and so on.

      Elaine, however, is the big fish in the small pond who tries to stay that way via passive-aggressive texts in The Voice of Sweet Reason Because She CARES or Is Just Passing Along Helpful Info from CEO! (Chirps!)
      OP, block her texts and keep your focus on your work. People like her are best ignored. Fob her off as needed. “I turn off my phone at night so I can rest undisturbed.” “Didn’t get the text.” Repeat.

      I’d also limit Elaine’s info about your schedule and work projects, other than meetings the CEO is directly involved in or unless he insists she’s copied on everything. It’s a fine line to walk, but some people just don’t need to know everything and she’s one of them.

  12. Lab Boss*

    Leaving aside some other weirdness with your company that seems to be in the letter, I can say that one thing that’s worked for me in this type of situation is going straight to the person who allegedly has the problem to sincerely address it. Leaving out any of your suspicions about Elaine, if you can convey the attitude of “oh goodness, Elaine let me know there’s a problem, let’s make sure it doesn’t happen again!”

    If the CEO was behind the communications then you’ll get info about what he wants, straight from the horse’s mouth, and deal with the issue if he’s trying to hold you to some special standard. If he’s confused or denies ever saying those things, you can blow it off with an “oh, must have been a miscommunication.” You know to ignore Elaine, he knows Elaine is speaking in his name, and you get to walk away squeaky clean having not “made an accusation” but just tried to correct a problem the CEO saw in you.

    1. IndustriousLabRat*

      This is a REALLY effective technique. The couple times I’ve had to do exactly this, in somewhat similar situations, it was like… an instant ceasefire, by showing the obnoxious party that I was fairly unbothered; just confused, and would not provide drama, even with significant goading.

  13. Snarkus Aurelius*

    Go to the CEO directly without accusing Elaine. Let him know that you’re getting these directives and that you’d like to have an overall conversation about your attire because you need to know if you’re erring somehow. You want to minimize one-off corrections.

    Approach it as you want to be helpful.

    Then YOU HAVE to report back!

  14. theletter*

    With the CEO loudly criticizing dress code violations in the office, perhaps some of his private complaints with her were interpreted as edicts that she needed to communicate?

    Was there a sales rep in the past that needed constant reminding to dress conservatively when meeting with the church-y clients?

    What might work best is to clarify with her that while you appreciate the effort to help, you and the CEO have an understanding regarding the dress code and so you don’t need early morning reminders or notifications. If it’s framed as a ‘Good news! You can sleep in past 4 AM because I have this covered!’ she might get the message that this is not part of her job description.

  15. Kittykuddler*

    Count me in the talk to the CEO camp. Again, I wouldn’t frame it as an accusation, but that you are getting texts at unusual times about your wardrobe choices and you’d like clarification going forward so there are no more 4am texts. Even if he’s saying these things, 4 am is inappropriate to be texting anyone in a non emergency situation about work.

    1. El l*

      I think that’s the only real option that makes sense – talk to him about it. “Hey, Elaine is sending me messages from you at 4 am about my wardrobe – do you have something you want to discuss? I mean, are those messages really coming from you?” I bet this type of male would run hard from any accusation of female wardrobe dictation.

      The only thing that empowers bullies like Elaine is that they bet nobody is ever willing to do anything about their behavior.

  16. Colorado*

    Oh my OP. The only person I would even remotely tolerate this from is my mother, and I’d have her schedule a doctor appointment the same day. I hope you keep your phone on silent or out of your bedroom. This is banana pants and your CEO is off his rocker. I personally would confront Elaine, ask for further clarification on these requests, and tell her to stop texting you outside of work hours. Then I’d be going to the CEO. Good luck and keep us updated!

  17. AndersonDarling*

    I had this happen to me. An admin was saying “VP wants you to do this now” or “The VP doesn’t like what you did with this presentation” and I was getting really suspicious that the VP, who worked in another building, was hearing about my activities in real time. So when “Elaine” told me that the VP wanted me to change a report, I picked up the phone and called the VP.
    “Elaine told me how you wanted to make these changes to the report, but I wanted to make sure you understood how that will impact the displayed information…”
    Ten minutes after I put down the phone “Elaine” was blowing her top because the VP called her to ask what the heck was going on. It was an epic meltdown. But she never put words in the VP’s mouth again.

  19. Lucious*

    Question- does LW definitively know Elaine isn’t authorized to comment on the CEOs behalf? They may have a one-on-one agreement in this area that empowers Elaine to speak on his behalf.

    1. doreen*

      That might make sense if it the comments were more generic – something more like ” As per the CEO, the dress code requires that skirts be below the knee” or ” As per the CEO, your TPS report is due on the fifth of the month” . But “as per the CEO” basically means “according to the CEO” and and doesn’t really fit if if Elaine didn’t have a conversation with the CEO specifically regarding the OP’s choice of footwear when it’s snowing or what neckline she should wear tomorrow. .

  20. shuu_iam*

    Since the CEO keeps strict boundaries between work and home, if you do end up asking him about the comments directly, it seems like it might be a good idea to mention the communications coming at 4-5 am. If he’s protective of his own boundaries, he’s more likely to understand why this is bad for yours. Even keeping it as a casual mention – “Oh, Elaine called me at 4:30 am this morning to let me know you had an updated policy about skirt length” – might still result in him going “4:30 am?!” and making those stop.

  21. Callyb*

    I am not sure I would do anything direct. Maybe ignore the messages from Elaine? Doesn’t seem worth it to get into these pronouncements.

    1. miss chevious*

      I agree. I would maybe check with the CEO once (ONCE) about my wardrobe to make sure it was fine by him, and then block Elaine’s ability to contact me except between 9-5 and ignore any of her edicts on this. From my experience with these kinds of EAs operating under the auspices of the Big Boss, it’s not worth raising because of the change of blowback (especially given your past experience here, OP), but there are also virtually no consequences for silent non-compliance if the issues are ancillary to your actual work.

    2. Beth*

      I would block her right away, no matter what else I did or did not do. She has no need to have OP’s cell phone number, and she’s abusing her access.

  22. Hales*

    I want to preface my comments with I believe the CEO acted unprofessionally when LW addressed the hierarchy issue with him originally. However, I also believe that issues of this nature simply cannot remain anonymous. If I am having issues with another employee that I want my manager to address, I have to okay with the fact that my statements are likely going to be relayed to that person in order for my manager to gain a fuller understanding of the situation.

    I understand LW’s hesitation to address this, but I also feel this is a different issue than the first time she brought something to the CEO. Elaine is trusted to carry out communications on his behalf. If these mandates are coming from Elaine, not the CEO, then Elaine is behaving unprofessionally, and it should be addressed. I think LW can frame this conversation with the CEO as, “I wanted to talk to you about my business dress. Do you have an specific concerns, or things you would like me to change?” If the CEO is actually the source of these statements, then this is his opportunity to address that directly with the LW. However, if he is clueless, this is LW’s chance to say, “Oh, well, I’ve received several messages from Elaine regarding my attire, so I wanted to get some clarification from you,” and provide him with the correspondence. CEO will likely communicate this to Elaine, which can be uncomfortable. But if LW really wants this situation to be resolved, Elaine is going to have to be part of that conversation.

    1. Artemesia*

      Yes BUT note that you are getting messages from Elaine at 4 am saying that HE has made these requests. This is the issue.

  23. CatCat*

    I really want to know more about Elaine. Are there other weird things that she does? Is there a pattern of weird things?

    Because part of me is wondering if it is her or if the CEO is really the weird one here and not Elaine. I know it’s not characteristic of how you’ve seen him behave with you OP, but I wonder if he may have different boundaries with Elaine. I mean, dude yells at people out windows to scold them about tight pants… yikes. That is super weird.

    3. Who Plays Backgammon?*

      It’s possible CEO put Elaine the Admin into the middle because CEO wants some dirty or annoying work done (like enforcing that pesky dress code) but doesn’t want to do it themself. And even if CEO did give Elaine those instructions, if other staff have a problem with it, CEO might duck the issue and claim they never said anything and leave Elaine holding the bag. My last manager was like a broken record: I never said that. I didn’t say that. And there’s the time-honored tradition of bosses saying the admin screwed up to cover their own asses.

  24. Dasein9*

    I once met a person socially, A, who started to text me things like, “You should check on T.”
    Thinking there was something wrong, I contacted my good friend T to check in.
    All was fine, as I discovered after a bit of back and forth.
    It’s just that A likes the feeling of power that comes from getting people to do things. She told me this with all good cheer and seemed very perplexed at my responding that the word for what she was doing is “manipulation” and it was unwelcome.

    LW’s description of Elaine puts me strongly in mind of A.

  25. tab*

    “post them all on a Things Elaine Says Twitter account, which I would happily read.” Add me to the list of people who would happily read the “Things Elaine Says” Twitter account.

  26. MissBaudelaire*

    OP, I’d be blocking her number between the hours of 6 pm and 8 am. You’re off the clock, so whatever the CEO wanted to tell you can wait until the next day.

    I also agree that I would take it up with the CEO. “The text I got said my neckline was too low yesterday. I’ve worn that shirt before and it hasn’t been a problem before. I just wanted to clarify what you didn’t like.” or even “Thank you for the concern you expressed about my foot wear. I just wanted to let you know I understand how to dress for the weather, you don’t have to worry!”

    If this is really Elaine (and I think it is), the CEO is gonna go “I have no idea what you mean…” show him the messages. Because if Elaine is speaking on CEO’s behalf that way, CEO should know. It would make me wonder what else Elaine is doing behind CEO’s back and in their name.

    1. Artemesia*

      I’d be inclined to respond back on the texts copying the CEO so he sees the messages — with your query about clarifying. Sort of ‘I understand you have concerns about my attire — should we meet to discuss it’ while sharing with him the messages you are getting at 4 am

  27. I WORKED on a Hellmouth*

    OP, please go to the CEO! Talk to him as if you are assuming these messages really are coming directly from him. Alison’s suggested “I keep getting early morning texts and calls from Elaine saying she has requests from you about what I wear to work, including my shoes and my neckline. Do you have concerns about my work attire that we could discuss directly?” is pretty perfect. And then go into more detail from there–“I fielded a 4:30am phone call about concealing my cleavage more and making sure my knees are covered when I sit–I have always felt you were comfortable being direct with me, so having Elaine convey these messages to me makes me worry that we are no longer on the same page and I would like to remedy that.” Honestly, this isn’t anything like that situation where you got pegged as an accuser–this weird lady is calling and texting you at 4:30-5:00am and saying YOUR BOSS TOLD HER TO TELL YOU TO COVER YOUR SHOULDERS, KNEES, AND TOES. If she says your boss said, then she should not be surprised when you talk to your boss about it! And if your boss DID NOT say it, then he absolutely needs to know what this lady is doing! If you bring it up in the right way you’ll be alerting him without coming across as tattling.

    And then please update us, because I am now invested and want to hear about you not having to hear from Elaine in the wee hours of the morning anymore.

    1. I'm just here for the cats*

      Also, I sure hope that the OP has saved the text messages/ call log so that she can show the OP. I can totally see Elaine saying that she never did anything like that.

    2. drpuma*

      Oh, I love your suggestion of “I thought we had the type of relationship where you’re comfortable being direct with me, did something happen?” Reading you point that out, too, just underlines how weird Elaine is being.

  28. T. Boone Pickens*

    I’d just….completely ignore Elaine and fire up a ‘things Elaine says’ Twitter account. OP, you’re in sales which means you’re the revenue engine that is driving the company. Your position is immeasurably more valuable than Elaine’s (unless Elaine is a fixer and your CEO has a habit of committing crimes on a regular basis) so I’d stop looking at these messages as annoying and start looking at them for what they are which is a mix of lunacy and comedy.

    1. I'm just here for the cats*

      Yes. And on most phones you can block calls. On my Google phone I have it so I don’t get calls/texts unless its from certain people or if the same person calls back within 10 minutes. That way if there’s an emergency, such as the person I’m guardian for is in the hospital in the middle of the night I can get those calls. But if someone from work (which has never happened before) calls/texts then I don’t get woken up by the message and can deal with it when I’m ready.

    2. Lizzianna*

      I wouldn’t bank on being more valuable to the company. (1) CEO doesn’t necessarily sound rationale, (2) regardless of how the numbers work out, the relationship between a boss and a long-time assistant is hard to quantify, and (3) assistants have a lot of power to shape the narrative in a conflict with another employee.

      Like, I would still ignore, but I’d keep a copy of my resume up to date and not assume that I’d get picked over Elaine if things came to a head.

      1. Observer*

        Like, I would still ignore, but I’d keep a copy of my resume up to date and not assume that I’d get picked over Elaine if things came to a head.

        Also, keep the resume updated and keep an eye out for better opportunities, because this place sounds nuts.

  29. SomebodyElse*

    I agree with the other suggestions about a carefully crafted conversation with the CEO.

    Next time you meet with him try something like this. “Rupert, I think we need to move up the paperclip sorting project if we want it to be included in the trade show. The binder clip project is a little behind schedule but we should be able to make it up during testing. Oh, and I just wanted to check in with you over your concerns about my footwear on snowy days. While I appreciate your concern about my safety, I’m not sure that I’m comfortable with the other messages in the off hours about my choice in skirt length and other wardrobe choices. Is there something we should discuss?”

    If nothing else it should kill lots of birds with one stone. Whoever is originating the messages about your self-described perfectly acceptable and professional wardrobe needs to stop. I can’t imagine working in a place where anyone would think it acceptable to send these messages to a senior member of staff. This is so bizarre. The conversation should also allow for the CEO to state directly if he has a problem (which see the previous statement) and that tells you what you need to know to decide if it’s where you want to work. It also will hopefully(!) clue in the CEO that his assistant is nuts. Once again, if he’s ok with that, then you’ll know what you are dealing with and can decide if it’s a deal breaker.

  30. Persephone Mongoose*

    Apologies if this is inappropriate/off-topic.

    LW, I’m assuming the turtleneck and chest-binding-using-an-Ace-bandage line was tongue in cheek, but just in case, either for you or anyone else reading: please don’t use Ace bandages for binding; this can cause serious internal injuries if done enough. Invest in a good chest binder instead.

    I agree with others that Elaine does not get to dictate what you wear to work. It sounds like the CEO would have no problem approaching you directly about it (though I take issue with how they do so based on your example) and unless and until you get direct feedback from them, consider yourself in the clear and feel free to cheerfully ignore any future missives from Elaine about your workwear.

  31. I'm just here for the cats*

    OP just talk with the CEO but don’t accuse Elaine of anything. Like others have mentioned just ask for clarification since he has been asking elaine to send you messages. (who knows maybe he did at some point ask Elaine to remind you to wear a longer skirt and she just decided to send it to you at 4 am)

    But I think the biggest problem here is the CEO is commenting on peoples bodies. yelling out the window (where not only other employees but maybe customers and the general public can hear) is not the right way to address a problem with the wardrobe. And I wonder why he was looking out the window in the first place if he was supposed to be in a meeting.

    This is why HR needs to have more control than just hiring and benefits. I think this borders on discrimination. OP you should probably take a real good look at this company. Is this really where you want to work. Where you can’t bring problems up to your boss without him losing it and sending mass emails naming you as the accuser.

    1. Sea Anemone*

      “And I wonder why he was looking out the window in the first place if he was supposed to be in a meeting.”

      What an odd thing to pick out. People naturally look in different directions both during conversation and when watching a presentation.

  32. River Otter*

    Ignore the texts.
    Only answer calls during standard working hours (or a little bit before and a little bit after). When you get a stupid message about what kind of shoes to wear, cheerfully say, “thanks for The update!“
    Enjoy the freedom of reclaiming the space in your head.

  33. DANGER: Gumption Ahead*

    I would just ignore her and see if the CEO said anything about it at some point. They don’t sound like they are exactly hesitant to address things, so if you really were defying their order you’d learn about it pretty soon. Then you’d know they did come from the CEO and to pay attention, or (as I suspect) learn that this was just Elain being weird

  34. Rusty Shackelford*

    LW, I understand you don’t want to look like you’re “tattling” on Elaine, but this is different from your earlier situation. If you reach out to clarify with the CEO, either (1) you’ll find out Elaine truly is speaking for him, or (b) he’ll find out Elaine is claiming to speak for him, which is something he definitely needs to know.

    1. The Rafters*

      Absolutely, otherwise, like the boy who cried wolf, Elaine may someday have to send a legit text and OP will ignore it as one of Elaine’s usual nonsense, and then OP may get in trouble with the CEO. Cut this nonsense off before something like that happens.

  35. Rav*

    If the boss is the type of shot from the hip person, I would approach it in a conciliatory tone: “I’m receiving messages about my wardrobe. Do you think any of it is inappropriate?” (Or something along the lines.)

    The idea is to put you in a position that you have to answer if the ceo wants to dig deeper.

  36. Susie*

    This sounds like an unprofessional work place. The CEO is leaning out a window hollering to someone about yoga pants? Combined with the proof that these messages came in while the CEO was off, and he’s strict about work/home boundaries, I think you have to say something to the CEO. Use any of the excellence suggestions above

  37. lost academic*

    I really have to second everyone who’s saying that you should address the requests directly with the CEO while entirely leaving Elaine out of it – literally do not even hint at the messenger or a third party. Keep the discussion where it belongs, between you and the CEO. Then you will know if you are free to totally ignore Elaine as I expect/hope you will (and should anyway) or if there’s just further bizarre dynamic going on and you might want to step up your job hunting game. But don’t make it entirely about Elaine – and to do that safely, you have to make it entirely about something else.

    But if the CEO felt it was appropriate to open your window and yell at someone for wearing tight yoga pants I am inclined to think there’s a little fire under this smoke – if I had to guess, I would say the CEO makes comments about things to the assistant, likely not even specifically about you, and she’s interpreting them when she hears/sees them and acting on them. Still – I think I’d simply ignore her entirely – I wouldn’t totally block her number if she’s ever had reason or could have reason to communicate something urgently to you, but I might do so otherwise.

    1. londonedit*

      Yeah, it sounds like Elaine is a busybody who thinks it’s her job to police everyone’s behaviour and clothing ‘on behalf of’ the CEO, but it also sounds like this place is completely dysfunctional if the CEO himself is liable to go ballistic on the strength of one email or one pair of yoga pants.

      I’d definitely speak to the CEO and try to leave Elaine out of it (though I think that might be difficult to accomplish seeing as these messages are coming from somewhere – even if the CEO knows nothing about them, surely his first question will be ‘Who told you I had a problem with your skirt?’) and I’d also definitely put my phone on Do Not Disturb outside of office hours – you can set up a list of contacts whose calls will still come through, and you can set it so that anyone who calls back twice will go through, but there’s absolutely no reason why Elaine should be disturbing you with these texts at stupid o’clock in the morning.

    2. Despachito*

      But if OP does NOt mention Elaine, and the CEO does not know anything about it can come off as weird (and can potentially damage OP).

  38. Clorinda*

    There are two and only two rational and workable responses here, and those are (1) ignore, ignore, ignore, or (2) confirm dress code with CEO and ask if you’ve ever had a problem being in compliance.
    If you really can’t ask the CEO if there’s a problem with the way you dress, there are still two rational responses, and those are (1) ignore Elaine and (2) start shining up the old resume.

  39. kittymommy*

    Yeah this is odd. Granted as an assistant with what would probably be considered CEO(s) at a private firm I have received texts very early in the morning with information they only send to me to have me pass along, but it’s never anything like this (and honestly if any of them told me to monitor skirt length or cleavage I’d ignore it). This definitely sounds like an Elaine being “particular” (and possibly a little sexist with the skirt thing).

  41. shalimar*

    Forward the message to both your boss and add Elaine–“putting us all on the same text thread .. so we are all on the same page. Got this message above from you Elaine and am letting you and CEO know that I received it. “

  42. TiredTurtle*

    Does it strike anyone else as sketch that the CEO was yelling out the window about yoga pants? Like there is just…a lot going on here.

    1. The Rafters*

      The CEO was way out of line for that, except of they actually were in the office at work wearing them. The person in yoga pants may have been out on a lunch time or after-work run. We have a number of people whowear yoga pants in the building b/c they changed directly before or after going to the gym or for their run.

      1. All the words*

        When we were all in the office lots of people wore leggings, jogging pants and yoga pants because they’re comfortable, regardless of the dress policy.

        Sadly, management proved to be willing to chastise someone for a dress code violation, but absolutely would not ask staff to wear their masks properly (or to simply wear one). Priorities, right?

      2. Liz T*

        They couldn’t have been in the office–he yelled out the window! That is a nutjob move however you slice it.

    2. Neurodivergentsaurus Rex*

      100%. And the way he reacted when LW brought up an issue with the colleagues was not good either. I think this company is full of bees.

    3. Gary Patterson's Cat*

      Eh… It is hard to say without more context and the actual comment. Agree it does sound really bad, but it could’ve been someone the CEO has a long working relationship with and it may have been said more jokey or mock-chastising without the CEO really being mad. Some workplaces are like that if the culture involves a lot of ribbing each other. I’ve heard many a CEO put foot in mouth and say things they ought not to say, even jokingly.

  43. Fire Ferret*

    Ok all good comments about how to address this specific issue, but you may want to take a step back and look at the bigger picture. You have a boss that seems volatile and willing to fire employees on a whim and over minor issues, no way to address work concerns you have, a coworker who has zero boundaries and seems to be using the CEO as a cover for her outlandish behavior, and an impendent HR. Are you sure you want to work there?

  44. Lizzianna*

    I have definitely worked with people where a manager will make an off-handed remark about preferring things to be a certain way, and then the staffer takes that as gospel.

    Like, “Oh, the photos in this conference room seem kind of dated.” And then the next thing you know, the staffer is urgently redecorating the conference room, and the manager is surprised because they thought they were just making small talk.

    I wonder if that’s what’s happening here, the CEO has expressed a general preference for things to be a certain way, and Elaine has taken it upon herself to be the enforcer of those preferences.

    In a functional workplace, I’d bring it up to CEO – not in an accusatory way, but just, “Oh, Elaine mentioned that you have some concerns about my wardrobe, could you clarify? I want to make sure I’m in line with the office dress code.”

    But if your workplace doesn’t lend itself to that, I’d just ignore the messages from Elaine. If she says anything directly (which I doubt she would, because her emails seem weirdly passive aggressive), I’d just say, “Oh, CEO never said anything to me, I thought this skirt was appropriate for the meeting. What exactly did he say?” But I would also keep an up to date resume, because this doesn’t sound like a functional workplace, so I would want a plan B if things went south.

    1. Gary Patterson's Cat*

      This is most likely. I’ve worked with that kind of EA. And sometimes they hold on to the role of enforcer even if you tell them “I just spoke with the CEO and they told me X, so you can check with them if you like.”

      It’s either very passive aggressive, or it’s a cover their butt thing if the CEO is kinda nutty and flip-floppy.
      But it sound here like the CEO is pretty direct about stuff when talking to subordinates according to OP?

    2. The OG Sleepless*

      I used to have a coworker like this! Jane was a dotty old busybody who absolutely adored our boss; I mean, she was like someone from a previous century who had sworn fealty to their lord. The boss mentioned in a staff meeting once that she wasn’t sure we should have something in a particular area; I said it was really useful for X reason. She said she would think about it. The instant the meeting was over and people were getting up from their seats, Jane was uninstalling it and practically running out of the room with it. That kind of thing. The thing was, the boss just thought she was amusing and figured she was retiring soon, so she just sort of let her be. So nobody else took her seriously. She stayed longer than anybody expected, earnestly carrying out what she thought her beloved boss’s wishes were and making a nuisance of herself.

  45. JKateM*

    Maybe it’s like Mr. Mahina. Soon Elaine is going to be telling her the CEO told them to switch parking spots.

  46. Gary Patterson's Cat*

    In this case, I think you do need to discuss it with the CEO directly, but I would shorten the ask.
    “I keep getting early morning texts and calls from Elaine regarding work attire. Do you have any specific concerns we could discuss directly so Elaine does not need to keep repeating this via email?”

    And I do think you are right that these are coming from Elaine and NOT the CEO. Possibly because they’re taking a comment the CEO made and then giving themselves the authority to spread the directive, even if the CEO didn’t issue it directly.

    1. Gary Patterson's Cat*

      It’s super annoying. I mean, one time is ok, but to keep issuing these is really overstepping unless the CEO actually IS issuing them (in which case he should address the dress code directly with HR).

  47. Cobol*

    I disagree with this feedback. This seems like a pretty toxic organization. Opening up a window to tell about right yoga pants?!?!?!

    LW I think would be better served by deciding whether they can accept the current environment or not. I’d pretty much let anything Elaine says go in one ear and out the other.

  48. June*

    I’d be very wary of going directly to Elaine. Someone like that will twist it and use it against you. For me, I’d approach the CEO very kindly and professionally to get “clarity” on the dress code and not mention Elaine at all until he asks “what are you talking about”?

  49. TinaTurner*

    There’s always calling the Asst. at the crack of dawn, to ask her about your outfit for the day.

    Seriously, if it were only TEXTS I’d think it was hostility. But calls at those times seem very aggressive and deranged.

  50. irene adler*

    If ever there was a situation in need of malicious compliance this is it!

    Obviously don’t do this, OP.

  51. Huh*

    If Elaine is only targeting women with these dress code “concerns” she may be causing a legal issue, and attributing the comments to the CEO could show them in a different light than intended. Elaine may be making a bigger problem for herself and Rupert than either of them realize.

    1. Gary Patterson's Cat*

      Oooh! I hadn’t thought of that. Were these only about female attire or were the messages about other things too?
      I thought maybe this was just an example.

  53. anonymous73*

    If you don’t feel you can resolve this by talking to the CEO, Elaine or HR, I’m not sure what you’re looking for quite honestly. The only thing I can think of is ignore Elaine, and put her texts/emails on Do Not Disturb unless they’re within reasonable hours of the day. Outside of that, you’ve removed every other legitimate option. Although looking for a new job could be an option because it sounds like an unhealthy environment.

  54. Sarah*

    This company sounds horrid. Yoga pants? Even if they break dress code, talk with them about it, don’t yell out the damn window!

    1. MissBaudelaire*

      This, too! If someone is breaking dress code and you need to discuss it, yes okay, do that. But opening a window to holler at them? That’s like what something Miss Hannigan would do.

  55. Undine*

    You could go to Elaine and say, “On one level it’s none of my business what you are doing with Boss at 4 in the morning. But if you keep texting me when you’re with him, you are dragging me into something I want nothing to do with.” In the end that would make more drama, but soooo tempting.

    2. Observer*

      Well, if the OP has another job they are going to, it would be the PERFECT time for such a response.

  56. ___JustNo___*

    Our CEO had an equally annoying and officious secretary at one point. She would talk to other coworkers with a smug look on her face and say “it’s coming down the pike” about any future development, including ordering furniture or acquiring another company.

    Eventually she was demoted because – shocker – She blabbed a highly confidential story about a married executive who was having an affair with another married executive. It seems that Mrs. Exec A wrote a letter to our entire board of directors complaining about the atmosphere of our company that led to this peccadillo and about Executive B, the affair partner. Some jobs were lost and it was an overall scandal, but at least the unofficial mouthpiece got banned. Yours may end up in the same boat!

  57. J*

    Don’t know anything about Elaine, but in my last job I was the assistant to a similar sounding CEO, and trust me, I did NOT want to be sending emails like this to staff but he asked me to so I had no choice. CEO might have just had a meeting with Elaine about this and asked her to periodically send out these reminders, so that’s why they are coming at odd days and times. I agree with another pp’s suggestion to reply to Elaine while cc’ing the CEO saying “of course”

  58. Essess*

    this absolutely needs to go into a communication with your boss. If you work directly for your boss, you should be able to go into the boss’s office and directly ask what concerns he has about your dress code “since he has been expressing his concerns in the 4am texts.” You aren’t tattling, you are trying to make sure you follow his ‘directions’ with clear understanding, just like any other work requirement.

  59. Becca Rosselin-Metadi*

    The early morning calls are clearly designed to get to her before she gets dressed but I would never pick up the phone after that first call and I’d consider blocking her. Make her put the requests in writing so there’s a paper trail.

  60. Batgirl*

    Something I might do, one day when I’m wearing a typical outfit example, is say to the boss: “I’m just wondering if this type of outfit meets the dress code requirements, given there’s been a lot of reminders to follow dress code”. Even if he doesn’t ask any follow up questions, or seem inclined to check Elaine, I would then start responding to Elaine: “Thanks for these reminders, I’ve checked in with the CEO about the dress code I’m to follow going forward”. Then block away with impunity. Meanwhile Elaine gets to feel rattled about whether the jig is up.

    1. Grumpy Elder Millennial*

      I like this strategy. You get some clarification on the situation and back-up, but without bringing up any of the awkward stuff.

  61. CM*

    Is it possible to talk to the CEO and Elaine about it at the same time? Then you can either say to the CEO in front of Elaine, “Oh, I had a question about the wardrobe requests Elaine has been sending me. Are there any concerns about the dress code I should know about?” or say to Elaine in front of the CEO, “I got your text this morning about my shoes,” and then turn to the CEO and say, “are these OK?”

  62. Qwerty*

    I wonder if Elaine is trying to prevent the CEO from going off on something and its just…snowballed. If he has “bouts of exuberance that seem to end in terminations”, interrupts a meeting to loudly chastise someone for tight yoga pants, and responded to a workplace concern with a barrage of emails about the “accuser”, then clearly he gets set off easily. In the spirit of toxic workplaces warping your sense of what is normal, I could see Elaine having started off trying to prevent people from triggering an outburst from the CEO, especially since she’d be so close to to fallout and eventually becoming obsessive about it. (Devil Wears Prada comes to mind as the spectrum – both the Emily assistant who ran around trying to avoid anything that bothered her boss and the photographer guy who gave Andi pumps to wear on her first day lest the boss see a woman in flats)

    If that sounds plausible, then try having a non-confrontational conversation with Elaine, as difficult as that might be. “Elaine, I’ve been waking up to calls and texts from you about my wardrobe – what’s going on?” Simple, open ended, let her fill in the gaps. If it doesn’t prove fruitful, end with something bland like “that’s interesting” to avoid the difficulties you’re afraid off and use the advice of do not disturb mode. But you might end up learning that the environment is pretty toxic so you can make your career plans off that.

    To be clear – I’m not justifying what Elaine is doing! I think understanding the motivation helps inform how diffuse the situation since this office sounds like a powder keg.

    1. Grumpy Elder Millennial*

      This is a really interesting point! There may be some rationale for Elaine’s (super weird!) behaviour that we’re just not seeing. Doesn’t mean it’s a good rationale, but there might be something else going on that’s influencing her. And yeah, I would not enjoy working for a CEO like OP describes. If someone yells at me about my clothing from another room, in front of everyone, I’m going to start working on an exit strategy immediately.

      Having a conversation with Elaine that you approach with the assumption that Elaine is trying to help you (even if she’s doing that in a super weird way) could give you some insight about things you might not be aware of. And if Elaine is just on a weird power trip, you’ll be able to be more confident that this is what’s going on.

    2. armchairexpert*

      I think this is a really good point. If I had to guess, I’d say that Boss has either complained to Elaine about OP’s dress in the past, or has gone on long rants about What Women Wear To The Office These Days in general. And Elaine is trying to warn/help OP at the same time as avoiding the rants herself.

      One thing that abusers do very effectively is to train the people around them to anticipate their needs and be proactive in doing things to avoid ‘setting them off’. And sometimes, how that plays out is for their victims to make unreasonable demands on other people, rather than risk the wrath of one. It might seem like a huge leap to say that this boss is abusive, but he doesn’t have to be in a strictly legal sense: even if this is the only subject on which he gets yell-y, it might be enough for Elaine to want to avoid it. I can see her getting anxious about it overnight, worried about whether OP will come in That Dress With The Neckline Again, and texting her about it at 4.30am.

      All of which is just back story, obviously. I think I agree with the actionable advice to talk to Elaine first, in a non-confrontational “what’s the deal” way. She may double down, she may play it innocent, or she may be like “I know, I KNOW, but Boss is just a nightmare about this stuff..”. Whatever the response, you have more information than you do now.

      1. Goldenrod*

        “One thing that abusers do very effectively is to train the people around them to anticipate their needs and be proactive in doing things to avoid ‘setting them off’. And sometimes, how that plays out is for their victims to make unreasonable demands on other people, rather than risk the wrath of one.”

        Oooh, this is so smart! I agree with this. Totally reminds me of my last job.

  63. RB*

    Oh, Alison, you seemed almost surprised by the situation, but in my experience, women policing other women, even to the point of persecution, is not that uncommon, especially with such petty concerns as this, and especially with personal appearance.

  64. Larry David's Glasses*

    oh my goodness, this reminds me of my coworker, who is a peer, but we report to the same boss. Whenever we have a meeting that does not include my boss and includes other team members (peers and surbodinates), she loves to say things like ” I spoke with boss and she agrees with me that XX is correct”, even when noone is disagreeing with her. It has gotten so bad that I keep a tally of how many times she says that in a meeting. Highest so far is 6 times in a 30 minute meeting. Not to also mention that she agrees with ANYTHING my boss says, even when she is wrong. One time, my boss said something that was wrong that she quickly agreed with. I then reminded my boss that the situation had changed and that the team had decided on something else. As soon as my boss was like “oh yeah” thanks for the reminder, she also said yes, I was also going to remind you about that. I was dying of laughter. Well, the joke is on me now because she is now getting promoted over me, even though I have been there longer and have more experience. It pays to kiss a$$ people!!!

  65. DD*

    I’m all about malicious compliance and if Elaine is sending me a text at 4:30am about something the CEO wants then I’m assuming that she just received this request from him or she would have sent it to me earlier. Which is going to lead me to – are the CEO and Elaine together somewhere at 4:30am in the morning? I’m answering back with things like – “Sounds like you are with the CEO can you ask him about ?

    That might flush out if it is a crazy pants CEO sending texts to Elaine at 4:30am that she is obligated to pass on or if it’s all Elaine. The amusement coming from Elaine trying to explain that she and the CEO are not actually together in the middle of the night is just extra.

  66. LizardOfOdds*

    Normally I prefer to be direct, but I wonder if OP could talk to the CEO about this indirectly without naming the person? Something like, “I heard through the grapevine that you wanted some changes to the dress code, can you tell me what you’re looking for?” Though maybe the CEO would know it was Elaine, or maybe the CEO would demand to know who is gossiping about the dress code. What a weirdo.

  67. Me*

    Sooooo I work someplace where the person in charge gives his admin assistant A LOT of room to act on their behalf as seen fit. And sometimes she’s way outta her lane. But also unless it’s something big, the boss isn’t going to intervene. He’s said as much, if it’s coming from her, proceed as if it’s coming directly from me.

    So I’m not so sure that Elaine is being malicious or out to get the OP as some have suggested so much as doing what she’s been told is in her purview, albeit and insane hours. And I also am not s sure that a boss who gets “exuberant” and then fires people is a boss who doesn’t make offhand remarks about what his staff is wearing and what he’d prefer. And I’d encourage you not to assume that just because your boss isn’t available to you when he’s out of the office, doesn’t mean he’s not in tough with Elaine. Again, the admin in out office is one of the few people who has a direct line to the boss.

    So I really think OP, your best option is the suggest of, of Elaine mentioned you want me to wear longer skirts, can you clarify your preferred length?” It’s going to tell you a lot about your boss and Elaine and how your boss manages.

  68. moonstone*

    This is so weird. Some of my thoughts about this are:

    – I second the advice to find a tactful way to bring this up to the CEO

    – Is it possible you can just ignore Elaine’s emails and calls? If you know for a fact that it’s not really from the CEO, is there any consequence to ignoring her?

    – I know this is usually a last resort type of advice, but I would consider leaving! Unless this type of lunacy is some industry standard, these people sound like a bunch of weirdos and you should consider leaving for a more sane workplace. It becomes a problem when everyone is a different type of Unreasonable, and you can’t bring up a strange problem with someone without it being misinterpreted on their end.

    1. Observer*

      I think that your second choice is ultimately the way to go. Not as in leaving without something else lines up, or even taking the first job you can get. But a sustained effort to find a more reasonable workplace.

  69. Pumpkin215*

    Why do you work at a place like this? I know that is not helpful but seriously, I would move on. This CEO sounds loony.

  70. Claritza*

    A new co-worker on our faculty came from a school where the principal was constantly claiming, “You must (or must not) [whatever]! It’s School Board Policy!” for anything unpopular he wanted to implement. By transferring to our school, she learned that NONE of it was “School Board Policy!”

    1. Observer*

      That reminds me of the letter where the Principal told a new teacher that it was policy for the teachers to pay for classroom supplies. If I recall correctly, there was some talk about how it was to show the community that the teachers were sharing the burden or something like that.

  71. esemess*

    I had totally forgotten about a semi-similar thing in my own life until I read this letter.

    When I was in high school I worked at the front desk of a gym. The front desk manager would leave signs behind the desk, in the break area, on the copier that said things like “Per Owner of Gym, NO ONE can use this copier without permission”; “Per Owner of Gym, EATING during your shift is PROHIBITED”; “Per Owner of Gym, NO STAFF may use x item”. It was always very clear to me, even as a teenager, that she was writing her own edicts on “behalf of” the owner of the gym and capitalize on everyone’s fear of the owner… Sassy 16 year old me ignored any sign that started with “per”. ;)

  72. LemonLime*

    Late to reply but I think your gut instinct about this not being the CEO is right. It was almost text book to a admin who worked for our director. She’d say things as if the director wanted it done/thought/ felt about a situation instead of saying it was her own personal opinion.
    “Director Bob says he doesn’t want to see anyone drinking coffee in their offices cause of spills and it looks sloppy.”
    *coworkers stirred into a tizzy and upset about losing their coffee privileges but comply*
    Me: “Weird, I was literally drinking a latte while talking to director Bob and he said nothing about it and then he also is a big coffee drinker and often strikes up convos at the shared coffee machine. Seems so out of character….”

  74. LMB*

    I can see the snow/shoes comment coming from the CEO if it were sent to the whole company as a reminder to prevent safety incidents, but it’s weird to single out one person.

    The CEO sounds potentially as bad as Elaine though. I can’t imagine a boss yelling out the window at an employee about their “tight” yoga pants, and firing people in reaction to any small issue is yikes.

  75. Betsy S*

    IJWTS – there’s some ‘weasel wording” here.

    Elaine says “as per the CEO” – that’s being read as coming FROM the CEO, but I first read it as “as per the CEO’s policy” – as in, Elain taking it upon herself to be the policy police.

    Reading it that way, my inclination would be to first ask her whether these messages did come from the CEO . If she says yes, follow the good suggestions above. If she says no, ask her to stop and if she doesn’t, treat it as harassment.

  77. nnn*

    I realize this isn’t the point, but I’m wondering what the nuance of the “appropriate shoes” comment is.

    In a vacuum, “there’s snow tomorrow so please wear appropriate shoes” suggests snow boots. But all the other comments seem to be encouraging a more conservative style of dress, which makes me wonder if the CEO is concerned that people are going to go clomping around the office in snow boots rather than wearing conservative office shoes.

    1. Observer*

      To me, the whole thing suggests that Elaine is using the snow as an excuse to tell the OP that she needs to wear less dressy (ie “flashy” or “sexy”) shoes. It’s still weird, because the whole situation is weird, but it would fit.

  78. Hapax Legomenon*

    OP, you have a CEO who randomly acts childish and fires people, an assistant messaging you at ungodly hours to complain about your attire, and you don’t feel comfortable going to anyone about your issues. The buzzing is coming from inside the workplace. If your job is full of bees and you are powerless to change anything, it doesn’t get better. You just get stung.

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