My COO and CSMO can't stand each other and I'm caught in the middle
September 30, 2019 1:06 PM   Subscribe

I love the company I work for--we're a <50 person startup. It's become increasingly clear that my boss (the COO) and our Chief Sales & Marketing Officer not only can't stand each other but are unable to put aside their egos for the greater good of the company.

I run a group tangential to sales such that I work somewhat closed with the CSMO and report to the COO. We are at a critical time in our organization as attempt to scale the business, hire more reps, etc. I started almost a year ago and am otherwise very happy--making good money, doing very innovative stuff, work 100% remote, make my own schedule, etc. From a culture/work-life balance perspective, it's an amazing company and has the potential to be a total game changer in our industry.

My boss--the COO--is a decent guy but is somewhat cocky and arrogant. Very smart but with a big ego. He leaves me and my team alone because he trusts that we know what we're doing (because we do). I have no problem with him beyond the way he's handling this situation.

Our CSMO is under ever-increasing pressure to close business and manage his national team of ~10 (soon to double in size) team. He's basically falling apart and deflecting his team's inability to close deals by coming up with "gotchas" that send my team and other groups within the company on wild goose chases to fix problems that don't really exist.

Our CEO is vaguely aware that there's an issue but effectively laughs it off ("COO has a big ego; ignore CSMO's complaints--I know they're not valid"). I do not think he has any idea how much the poison they've created is affecting everyone else's lives.

Finally--and maybe I'm burying the lede here--I was texting with CSMO late the other night and he called the COO a dick, that at our next executive meeting if the COO says "X, Y or Z I'm going to jump over the table and beat the shit out of him" . . . "He's so fucking stubborn and stupid", etc. . . I don't actually believe that he'll jump the table, but it's a bit alarming that he's thinking violent thoughts and indicative of his mindset. No question he told me these things in confidence, and I don't think I'm comfortable ratting him out.

I see perfectly clearly how each is both right and wrong in their own ways. I care about these people and want to see us succeed. It's all about ego and holding one's ground, stubbornly.

My question/problem is: how (if at all) do I address this situation? I am seriously concerned about how this broken relationship might bring down our organization in the short or long term. Do I pull the CEO aside and provide more details? Try to talk to each of them individually? Email them together and express my unhappiness with how they're both behaving? How do I do this tactfully such that it's clear I'm trying to help and don't have any ulterior motive beyond bettering the organization?

Other notes:

- The CEO, COO, and CSMO have all worked together at previous companies
- Everyone is remote--we all meet about once a month
posted by eggman to Work & Money (15 answers total)
 
I think this is probably just the way these guys operate, and they don't necessarily see it as being as destructive as it seems to you (and to me!). But I'm not sure it's really your problem, except in two very limited ways:

1) You get pulled into it with late-night texts. If you can draw a boundary about not getting into conversations like this, that's probably your best bet. Could be you saying to the CSMO, "Hey, dude, I'm not the right person to be having these conversations with. I know you and COO have a tough relationship but he's my boss and I can't get involved." Or maybe that's too direct, and you could, like, just "not notice your notifications" when these convos start up. Say you were at the movies. Heck, go to the movies! Any time the conversation takes a non-work-you're-actually-involved-in turn, whoa, your mom just called! Or your pasta's boiling over! Or a bird flew into your living room!

2) You're fearful that this dynamic will bring down the company. There's a really good chance that it will! And even if it doesn't, you know, startups fold - they either go out of business entirely or they lay off half their workforce a couple of times then go out of business. So you need to have an strategy for what you're going to do when the company goes out of business regardless, and in the meantime it's going to be a better use of your time to do *your* job rather than some kind of interpersonal management thing.
posted by mskyle at 1:27 PM on September 30, 2019 [7 favorites]


This is not your fight and I would be extremely careful wading into it, as of the four people in this story, you are the least senior and therefore the most expendable.

Feedback delivered into the wrong ear at the wrong could really blow back on you in a negative way.

My advice is to offer empathy ("it can be really frustrating, I know") but not take part by actively dumping on anyone else.

The late night sms sounds like frustrations boiling over in a high stress situation. Inappropiate? Yeah. Unprofessional? A little. But I've seen and heard worse and a late night vent is pretty low on my list of things to get worried about at work.

Try focusing on what you and your team need for success, rather than what you need others to stop doing if you have a conversation around this. Let the parties concerned connect the dots.
posted by smoke at 1:51 PM on September 30, 2019 [5 favorites]


How do I do this tactfully such that it's clear I'm trying to help and don't have any ulterior motive beyond bettering the organization?

The CEO, COO, and CSMO have all worked together at previous companies.

You can’t. I would try to avoid anything on the personal insult conversation side at all costs. Next time anyone starts venting to you, do whatever you can to change the subject. Do not engage. Do not warn anyone (unless someone in is physical danger). Do not try to play mediator. However bad their dynamic is (and it sounds terrible to me), it’s not new to them—but you are. They chose to work together despite already knowing each other. If a bigger struggle breaks out, you don’t want to become the chess piece in the middle. And you’ll go from the emotional sounding board to the betrayer who tattled to the other guy to someone who wasn’t a founder and thus can be made expendable.

And I know startup culture is very different from more traditional office jobs, but I highly recommend being the guy at work who’s unavailable to text at night unless it’s an urgent work matter.
posted by sallybrown at 2:02 PM on September 30, 2019 [3 favorites]


For the record, I'm quite friendly with the CSMO, am very good about drawing work/life lines, and actually initiated the late-night texting session mentioned. I'm not worried about that part of it . . .

Otherwise, good advice--thank you! It's just very hard watching something you have a vested interest in melt down and have little to no recourse.
posted by eggman at 2:03 PM on September 30, 2019 [1 favorite]


And while they're all senior--they're only slightly so . . . we're a very flat org. I sit on the exec team with them. My opinion counts and my voice is heard. I also have a fairly close and open relationship with the CEO.
posted by eggman at 2:05 PM on September 30, 2019


This is your company culture at work. If you are open and close with the CEO, you can schedule time with them and say, “hey, this antagonist relationship is creating unnecessary stress in the workplace. The CSMO is also kind of demoralizing everyone with the pressure they are exerting and I am wondering if something can be done to improve the situation. I know it’s affecting my morale and feelings of stability and it may be affecting others who might not feel empowered to bring this to your attention.”

You can also clarify that you have a good working relationship with both these individuals and you don’t want to harm that.

My personal caveat: if you are a woman, this’ll be the end of you. If you are a man, you might have a chance. But, sticking your neck out for the company good can have real consequences so know what your exit strategy is if they decide to ice you out or do nothing. If they do nothing then they have just established firmly a company culture of stress, bullying, and lack of accountability for key players.
posted by amanda at 2:28 PM on September 30, 2019 [7 favorites]


The irony is that this is very atypical for our company--respect, caring for others, transparency, accountability, etc. are all foundational to the company. It's JUST these two people, and they happen to be leaders--thus the poisonous nature of the relationship cascading down throughout.

I also feel very confident that sticking my neck out would NOT have any drastic consequences. If they did, I wouldn't want to work here and am otherwise highly employable. Part of the dilemma is that it's SUCH a great working culture (seriously, I do what I want when I want to from wherever I want, and I know I'm good at my job) that I don't want to give it up easily.

I think I inherently knew that there wasn't much to be done here--in fact I already had approached the CEO about this on a more casual basis, but it's gotten worse since . . .

Thanks again everyone!
posted by eggman at 2:35 PM on September 30, 2019


Not an expert, but here's a thought anyway.

If you can put together, in your own mind, a concrete case for how their animosity is damaging to the company and, potentially, to you and your livelihood, and maybe everybody else, and their kids -- you could bring that up with one or both of them, if you feel comfortable.

You might also find a relevant book and, if you're on those kinds of terms, and if they read business books, give or recommend it to them.

That's all I've got.
posted by amtho at 2:50 PM on September 30, 2019


It sounds like the CSMO is flailing and should probably be polishing their resume. Not that they sound like they're at risk of firing, but do they even see a light at the end of the tunnel as far as the static and roughness goes? It sounds like your team is essentially covering for him, deliverables-wise, so maybe a come to Jesus talk with him is in order. Take him out to lunch (on the company's dime, natch).
posted by rhizome at 3:00 PM on September 30, 2019


I was texting with CSMO late the other night and he called the COO a dick, that at our next executive meeting if the COO says "X, Y or Z I'm going to jump over the table and beat the shit out of him" . . . "He's so fucking stubborn and stupid", etc. . .

I’m not sure if this is your first startup but that is really tame. You’re blessed that it has largely been contained (as far as you know, working remotely) to the executive level.

Startups are pressure cookers and you get what you get as to how people handle it. Short of putting sedatives in the water supply there is nothing you can do about it.
posted by Tell Me No Lies at 3:57 PM on September 30, 2019 [1 favorite]


Regarding this:
The irony is that this is very atypical for our company--respect, caring for others, transparency, accountability, etc. are all foundational to the company. It's JUST these two people, and they happen to be leaders--thus the poisonous nature of the relationship cascading down throughout.

I hate to say this, but even if they say respect/transparency/etc. are core to the company, THEY ARE NOT core to the company if two of the core leadership team are acting this way. If assholes are in leadership and are allowed to be assholish without instantly getting shut down by the CEO, then assholishness IS your company culture. I speak from experience.

Your profile says you are a man so you may have a chance to push back on this (maybe following some scripts from Ask A Manager). If you are in any way not a cis white hetero abled male, I'd say get out of there while you still have your sanity.
posted by matildaben at 5:02 PM on September 30, 2019 [8 favorites]


The CEO, COO, and CSMO have all worked together at previous companies.

they have, but you haven't?

so, ok, don't put yourself forward in this in some kind of unasked-for mediator/counselor role, and when the CSMO texts you about what a prick the COO is, don't ever reply in kind just to be sympathetic. like, he says "I want to kill him," you can say "that sounds really rough" and "that sucks" and that's IT. just don't start saying "Yeah" because that leads to "Yeah he sure can be a prick sometimes" and on from there.

I mean if they know each other from before, but they only know you from here, that means his extreme language and insults may be forgiven if this all comes out, but yours won't. even if you were only ever agreeing with the other guy to go along and weren't sincerely taking sides. especially then!

you may say to yourself, But how ridiculous, how would our private conversations about the COO ever come out even if the CSMO loses his temper and starts yelling all his grievances in a meeting? don't say that to yourself.
posted by queenofbithynia at 7:24 PM on September 30, 2019 [3 favorites]


The CEO, COO, and CSMO have all worked together at previous companies.

I missed that the CEO had also worked with them in the past. In that case you definitely want to stay completely clear of this. They have a dynamic that works for them or they wouldn’t keep coming together.

For what it’s worth I spent a good part of my career startup hopping with a slowly shifting cast of coworkers. There were certainly times we were ready to kill each other, but we also had a bond of trust from watching each other perform as well as generally hanging out together for 15+ years. An outsider trying to comment on (or, god help them "fix") our group dynamics would have been the subject of tremendous ridicule among us no matter how annoyed we might be with each other that day.

There’s no winning for you here.
posted by Tell Me No Lies at 1:24 AM on October 1, 2019 [2 favorites]


If the CSMO can't cut the mustard, then the CSMO will lose if push comes to shove. Which is fine. You'll get a new head of marketing, they'll spend two weeks sniffing the place out, then they'll change the logo because the new head of marketing's first move is always to change the logo, then you can all get on with cleaning up the backlog.

None of this is anything you either can do or need to be doing anything about. Stay out of it to the greatest extent you possibly can.

And listen to queenofbithynia, who is wise.
posted by flabdablet at 2:20 AM on October 1, 2019


his extreme language and insults may be forgiven if this all comes out, but yours won't.

Yep. This. And this:

if you are a woman, this’ll be the end of you. If you are a man, you might have a chance. But, sticking your neck out for the company good can have real consequences so know what your exit strategy is if they decide to ice you out or do nothing. If they do nothing then they have just established firmly a company culture of stress, bullying, and lack of accountability for key players.

They are playing long-standing roles and nothing is seen as egregious... it's all part of the show, and part of their dynamic. You aren't in the cast... it's like you've been pulled from the audience to briefly take part in the production. And ultimately, nothing you do will have any effect on its outcome. But they may need you every now and then to shift the plot along. It's never your story that's being told, though.

If you start overstepping your "bounds" they won't stand for it. You don't really exist for them as a real person, and the more you remind them that you are a real person, it will eff up the flow. I think the more you assert yourself and try to change things, the more your job may be at risk.

This sucks for you and I join the others advising you to GTFO as soon as you can. You deserve so much better.
posted by I_Love_Bananas at 2:38 AM on October 1, 2019 [1 favorite]


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