How do I explain difficulties involving a fellow manager to our boss?
March 26, 2019 12:53 PM   Subscribe

I'm at my wit's end. One of my leadership peers, Riley, is almost twice my age and notoriously difficult to work with: passive aggressive, defensive, treats some of us like children, makes mountain ranges out of mole hills. Employees ask me how to work better with her, but nothing I do myself seems to help. Trying to explain what's going wrong to the CEO has proven difficult. I'm not even sure I'm handling this right anymore. Help me process and articulate this situation? How to discuss with CEO productively? Many, many details inside.

For reference, most employees at our company are between 25 and 35, Riley is at least in her early 50s and comes from a very corporate career background, has been with us for about 18 months. She was originally hired to do a job she's not currently doing. Our CEO has trust issues and relegated her to what she thinks is a station below her talents, she has said as much to me before our relationship deteriorated. Instead, she has slipped into a role at the center of our process, helping establish how we work together, and decide what's the biggest priority to focus on, without being accountable or responsible for those decisions.

Here's what I know and what I've seen:

Riley has been an ongoing challenge for pretty much everyone I've talked to about them since she joined the company. She has three employees reporting to them with no prior management experience. Unfortunately, our CEO is in the same boat also: no management experience, no set standards or expectations for management in our company. I kind of see this as problem #1. What even is a manager's job? Who knows! Everyone handles this differently. The CEO sticks to tactical things like process, and only has discussions with me about professional growth and such if it turns into a crisis and afraid I'm going to leave.

Problem #2 would be the way Riley treats others publicly. She gets defensive very easily and will start treating people in a demeaning way if she feels friction or hears disagreement. Sometimes, if you cause too much friction or don't play along with her way of doing things, a switch will flip for Riley, and she will start treating you like a child.

I've been put in the "child" bucket along with the CEO, one of her employees she recently shot down for a promotion to management because "he's not ready" (despite his years of management experience), and a handful of other employees (basically everyone who has asked me how to work with her better). What it looks like in practice is Riley questioning your logic, asking in fine detail how a proposed solution would work in an incredulous way, her tone of voice changes to something like the way you'd talk to a 5 year old, scoffing at suggestions she thinks are ridiculous, explaining to you why things are the way they are instead of answer your questions about how to do things differently, and getting shushed or cut off. Last week, Riley shushed her own employee in a group meeting run by someone else, to talk over them. My jaw dropped.

This behavior is infuriating but very hard to explain unless you're one of the people experiencing it. What is this kind of behavior called and where is it coming from?! Once you're in this bucket, it's very difficult or impossible to escape it. The CEO has witnessed some of it, but not her most egregious moments.

Problem #3 is just straight politics. In leadership meetings, she gets into it with the CTO (and used to with our former Art Director, before he was fired for causing too much friction and being unwilling to let things go). I refuse to participate in the bickering, preferring to debate productively, and it's easy for me to let go of being mildly disrespected if it means we can collectively arrive at a decision. I'm young and transparent with my emotions, my concerns, and my excitement. I want to be an ally to Riley, and expressed that early on, but she's put a wall up between us and never speaks honestly about how she is feeling even though it's very obvious to me. (This is a personal bother - unexpressed emotions get bottled up if they don't find an appropriate way to come out, which there is an abundance of going on right now.)

Because the relationship between Riley and myself has degraded over time, I now have to fight hard to be included and very frequently just get left out, even after explicitly asking and discussing with the CEO. My team is smaller numbers-wise than any other team in the company, so that puts us at a disadvantage and we frequently resort to inserting ourselves. Explicit conversation about this struggle with the other managers (including Riley) has so far resulted in little to no changes made. My team continues to struggle with this. The CEO's response to this particular piece has been "we are still figuring out how to incorporate you guys into the process". This is after several explicit suggestions of how to do so that bounce right off Riley, and things proceed as usual. Who is in charge of process? No one.

Problem #4: none of the employees who have been affected by Riley's behavior or actions have spoken up. They (understandably) feel afraid to talk directly to the CEO about this, so it often gets communicated to me or other managers - the CEO tells everyone they can always come to him and that we're a "flat-ish" organization (?! no one feels this way, I've said as much, he continues to say this), but this doesn't move the needle at all. The CEO has unwittingly created a culture of "everything is going great, nothing but positives, don't bring negatives to me". So no one does. And then, since I'm the only one continuing to do so, I am a lone voice speaking against what the CEO perceives as the general mood: if there's such a big problem with Riley, why am I the only person coming to him about it? My team certainly does, and I try to pass their words along to him, including explicitly stating "they're afraid to talk to you or Riley directly about this". He doesn't seem to see the problem. Which: ok cool ¯\_(ツ)_/¯

This isn't my first rodeo. I've been in software most of my life. I've seen variations on this theme before. I've run small companies before as the CEO. Candidly, the person above is toxic and should have been removed or replaced shortly after the problems were apparent - but this isn't my company. My previous solutions to similar situations have been to leave the organization and find somewhere else to offer my energy and my unique talents. This is pushing me in the same direction, but I'd like to do what I can and change what I can for the sake of our employees before I arrive at the same conclusion.

Potential silver lining?: We just hired someone who does what Riley was originally hired to do, who also reports to the CEO, so Riley might very well get pushed out of her role in the company and no longer be the linchpin around which process forms organically and how shit gets done. I'm willing to stick around long enough to see if this shift happened and if it helps at all.
posted by Snacks to Work & Money (9 answers total) 3 users marked this as a favorite
I would see how much you can divorce your work from oversight or interaction with Riley, TBH. Keep your head down, work around her, and stay on a positive course. If it were anyone but the CEO of your company who was pushing this person into your work, I'd say you possibly would have an avenue to explore in terms of changing the reporting structure or her role, but as she seems to have the unequivocal support of the CEO, then you'll either have to minimize how much her work style upsets you, or exit for another company.
posted by xingcat at 1:06 PM on March 26, 2019

Its sort of amazing how many Rileys are out in the work world... I have one right now at my job and just find it shocking they continue to be employed for us - totally runs counter to my organization's work culture, so destructive. Feel like there's always been one or two at every gig I've had.

But, I've also noticed that Rileys are often successful at convincing the person with the power (in our case, the CEO) that they are useful and matter. From what you've written, the CEO doesn't want to hear about how unlikeable Riley is, and specifically not from you.

You also seem to be expressing a lot of personal feelings toward her (totally justified, she sounds awful), but I don't think that talking about that will help you in your situation. Sometimes people are just irritating to work with, but the bosses' job is not to make you all friends - its to make sure the work is getting done in the best way.

In your conversations with the CEO, or whomever your direct supervisor is, you should emphasize how the outcomes of your work, in your area, are limited b/c of Rileys actions. You actually aren't saying much in your comment about how those actions hurt your work - do they? Or is she just kind of an asshole? If they do, you should simply, and impersonally, explain that to the CEO, like "Hey boss - our software numbers are less than they should be b/c Riley ignored our request for the widget spinners. This happens regularly. My team won't get our software numbers up until the widget spinners request is fulfilled."
posted by RajahKing at 1:27 PM on March 26, 2019 [8 favorites]

Try to explain to the CEO how Riley's behavior is a problem for him, not for you or your coworkers. I was successful getting through to a CEO about a problem employee by framing it as concern about how this person's behavior reflected on the organization and the leadership team, both internally and externally. I had a lot of concrete examples, laid out methodically and dispassionately, which made it pretty hard for him to ignore.
posted by something something at 1:38 PM on March 26, 2019 [10 favorites]

A CEO generally isn't going to care too much even if every single employee of every company and their own hated a manager. I think that's privilege of being CEO, a complete dissociation from the QOL struggles of the minions. To make an impact, I think you'd need to bring a case to the CEO that Riley is actively hurting productivity, profit, and the good operation of the business. If it comes across as just folks not-liking Riley, no matter how good the reasons are to dislike her, it will fall on uncaring ears. Light a fire under CEO's ass so they'll get up to notice Riley is starting fires everywhere and that the business would be better if just Riley was fired.
posted by GoblinHoney at 3:39 PM on March 26, 2019 [1 favorite]

It doesn't sound like the problem is so much Riley as the CEO. If Riley is the symptom of the issue, it's not going to get better if they're removed, it'll just be another Riley.
posted by Candleman at 4:19 PM on March 26, 2019 [3 favorites]

When you describe the Riley problem to the CEO, don't use metaphors like "she treats people like children." Only describe the specific behaviors - interrupting, repeating without explaining, insisting that questions are irrelevant, and demanding that people answer detailed questions on the spur of the moment.

And definitely describe the problem as one for the company, and specifically a problem for the CEO, not as "she's causing strife and other problems."

* She's reducing productivity. (If you can say by how much, because people are having to redo work or losing time because of her, that's great.)
* She's blocking useful changes (like the would-be manager she said wasn't ready); she's quick to declare what doesn't work, but doesn't have alternative solutions or ways to convert a non-viable proposal into on that could work. (In the case of the would-be manager: it sounds like she didn't say what skills or experiences he'd need in order to make him ready.)
* People won't complain to the top; they want to complain to their direct reports/managers. You, Mr. CEO, should not have to listen to every worker's individual concerns about their job conditions; that's part of what managers are for.

Bring up the gaps in the system. When he says, "we are still figuring out how to incorporate you guys into the process," ask who "we" is, and how you can schedule a meeting with the "we" people to discuss how your team can be better connected with the other teams.

Riley might very well get pushed out of her role in the company

Don't count on it. You may need to bring up the fact that (1) they no longer need her for her original role, and (2) she's not helping other tasks get done.

most employees at our company are between 25 and 35, Riley is at least in her early 50s

And this would be why she's likely to stick around - avoiding age discrimination in the workplace is tricky. If she's one of very few people over 40, it may look like "we're getting rid of the older people who just don't mesh with our culture, which is because we're all younger," which is discrimination. You may need to point out to the CEO that she's causing specific problems, not just "she doesn't get along with people."
posted by ErisLordFreedom at 4:26 PM on March 26, 2019 [5 favorites]

"Instead, she has slipped into a role at the center of our process, helping establish how we work together, and decide what's the biggest priority to focus on, without being accountable or responsible for those decisions."

use your own damn process, work on the things you prioritize highest. Send her scurrying to the CEO.
posted by at at 6:19 PM on March 26, 2019 [2 favorites]

You really need to look at
posted by Enid Lareg at 7:03 PM on March 26, 2019 [1 favorite]

I have faced a similar situation for the last 20 months or so, and my CEO in this case is close friends with Riley, which makes matters a lot worse. This approach isn't for everyone, but I'll say this much: a few weeks ago I decided I had had enough and spoke 1:1 with the CEO, diplomatically making the case why Riley was a risk to the organization as a whole (focusing on objective facts and concrete examples, and steering clear of personal differences).

And you know what happened? He agreed with me. Better yet, he removed Riley from my reporting line and I now work directly for the CEO.
posted by lecorbeau at 4:42 AM on March 27, 2019 [1 favorite]

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