co-op student is now our manager, do executives never get real time off, and more

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

1. Co-op student is now our manager

My department’s gone through a bit of restructuring when it comes to team leadership (in a few years, we’ve gone through three managers to reporting to a director). We’ve received news that we’re going to have a manager again and it’s someone from our team, a supervisor named Ryan.

Ryan was a co-op student in university and helping our department just six years ago. After finishing school, he was hired for an entry-level position. Our manager at the time, Angela, promoted him after four months to fill a sudden vacancy in a challenging position. Less than a year after that, he was promoted again to a senior position. He was barely there when the new manager, Jim, decided that Ryan was a good fit for team leader after a previous one was suddenly let go. It was finally a position that Ryan held for more than a year. While Jim was a good manager, the department was re-structured. The company decided we no longer needed a manager and team leaders, but instead would have two supervisors that would report to Angela, who was made a director. There were three team leaders at the time, Phyllis (who had been with the company for over 10 years), Andy (whose trajectory was similar to Ryan’s, but spaced out over five and a half years), and Ryan. Guess which two people were made supervisors and which one got transferred to another team? I was really incredulous that Phyllis, with years of experience in the industry and leadership, was moved.

As a supervisor, Ryan dropped a ball a few times. Workloads grew, quite a few people left the department (including a couple of star workers), people who had no experience were hired to fill vacancies, clients complained about our department’s deliverables, and some workers who previously received positive reviews were now mediocre at best. I suspect Ryan’s latest promotion has to do with the fact that he is friendly with a lot of higher-ups (which is ironic since he tends to be rude with staff from other departments).

Our department isn’t small; in fact, it’s one of the largest ones in the company, with many people who have been in their roles for over 15 years. Ryan’s degree isn’t even in management or business — it was in sociology (which has nothing to do with our industry). A few of us are baffled that he’s gotten this far up. I was showing him how to log onto our systems only a few years ago and now he’s my boss. I really don’t know why he’s been promoted so quickly so often, especially since he doesn’t have a great track record as a leader. Is there any way we can demand some transparency as to why he was chosen?

Phyllis and Andy have some standing to ask about it, as the other candidates for the job that Ryan got (particularly Phyllis, as a more experienced woman being passed over for an inexperienced man), but the rest of you don’t really have the ability to demand transparency about it. You can certainly express concerns — but given all you’ve described, I’m doubtful that it will do anything. It sounds like Ryan is getting promoted quickly because management likes him, and this is a company that rewards people based on relationships with higher-ups rather than on merit.

To be clear, it’s not impossible for someone who was in school six years ago to have this kind of rise based on merit — some people are really good at what they do, or good at leading a team in what they do, or good at schmoozing clients or something else that really matters in their role. But that doesn’t sound like what’s happened here, based on Ryan’s track record as supervisor. (On the other hand, it’s also possible that the problems you listed aren’t major concerns of your management and that they have other priorities that Ryan serves well.)

2. My manager is pushing in the wrong direction

I work for a company that produces a particular product under several different brands (let’s say teapots to stay anonymous). This company is very decentralized, and historically each brand has been able to do whatever they want, as long as they make money. A few months ago, I transferred internally into a new-ish (and fundamentally underpowered) central Design Oversight team as a senior IC. I see a lot of opportunities to contribute; for example, I could ensure we don’t accidentally design identical teapots across multiple brands, which is costly and has happened before.

My manager, Doreen, is a highly qualified external hire who previously managed teapot design at a different company. I like her management style and we get along well. However, Doreen believes that her job is to make sure all of our brands use the exact same processes for everything, like each having a specific council that would run quarterly reviews using specific templates and rubrics. This is not a bad way to run a business, it’s just out of step with the politics of THIS business. Basically, she wants to tell each brand how they should govern their own business, and she’s taking a heavy-handed approach to try to force our entire company to operate in the same way as her previous one.

When I discuss her ideas with the VPs and SVPs at each brand, they tell me their current processes are working perfectly fine, thank you very much. The CEO’s stated philosophy is that each division is an independent mini-company, with complete control over its resources. In the last town hall, the CEO (Jane) literally said, “I have no interest in making everyone do the exact same thing.”

Doreen is senior-ish, but certainly does not have the standing or influence to dictate something like this, and she’s not doing the stakeholder work to change anyone’s mind. The executives aren’t inclined to central governance. The brands are used to autonomy, and they don’t want to be told what to do. Personally, I don’t think we need what she’s suggesting either.

In theory, this is between Doreen and her boss, and I know they will sort it out eventually (timeline: months to years). But until then, Doreen is pushing me to campaign for her changes. So far I’ve held her off with “quick wins” that will get good results without directly pushing the bigger changes she wants, but that’s only going to work for so long. I think I have a good reputation within the company, including with senior leadership, and although I believe in the mission of our group, I don’t want to squander my political capital on this doomed initiative.

I wish she would read the room. I think she could do so much to help our organization, if only she would let go of this. How directly can I raise this with her? Do I go above her head? Do I have to shut up and go along with what she wants? Is there any way I can help to steer this ship?

Do you have enough rapport with Doreen that you could just say straightforwardly, “I think we’re running into resistance on this because the VPs and SVPs at each brand prefer to use their own processes and feel they’re working fine, we don’t have the authority to insist otherwise, and Jane has explicitly said she doesn’t want to make everyone do the same thing. To make any headway with it, my sense is that Jane would need to change her operating philosophy. So would it make sense to work with her on this first and see if she’s on-board? So far everything she’s said makes me think she wouldn’t be, so it feels like we need to hammer that out first.”

Also, if you have a good relationship with Jane (or Doreen’s boss, if it’s not Jane) and have an opportunity to bring it up with her, you could give her a discreet heads-up about what you’re seeing and suggest that she clarify with Doreen what she does and doesn’t want her doing in this regard. Or if you have a good relationship with one of those annoyed VPs, there might be room to discreetly suggest they have that conversation with Jane (although this one requires much more delicacy, so it doesn’t later read to Doreen as if you were purposely going around her to undermine her with the people she’s trying to influence).

3. Do executives just never get any real time off?

My husband is a VP at his company and manages several people. He reports directly to the CEO. There is also a COO above him. It seems like he can never take time off to really disconnect. He has generous PTO which he hardly ever uses. Usually at the end of the year, he is scrambling to use it all because he will lose it.

But even when he has planned PTO, he seems to always have work emergencies that he has to take care of. Sometimes they are only 15 minutes or so, but sometimes longer. And he’s always frustrated to be interrupted and have to work on his days off.

Is this just what they pay him so well for? Unfortunately there will be emergencies that come up that only one person can take care of and so you’re expected to do it even on your days off? Or is there a problem with not maintaining boundaries around PTO?

It depends heavily on the job. If he’s in, say, crisis communications — yeah, it’s part of the job that he’s going to be bothered on some of his days off. But it’s definitely not true that this just comes with the territory in all VP-level jobs (and even when it does, there are usually ways to plan for some truly uninterruptible time). And sometimes when managers function this way it’s because they haven’t trained their team well or deputized people to act for them in their absence, or aren’t being assertive enough about protecting their time away, or actually prefer to deal with things while they’re away so they don’t have surprises when they come back. Other times they’re in a dysfunctional culture that expects this of them.

It’s hard to know which is the case here — but it’s a conversation you could definitely have with your spouse!

4. Should I ask for a vacation pay-out when I leave even though we have unlimited time off?

I work at a mid-sized company, with a mix of exempt and non-exempt employees. I’m exempt (and should be). I accepted my job with a fixed amount of vacation time, but during my first few weeks, the company changed its policy to unlimited vacation for salaried employees.

Now that I’m looking to leave, I’m considering whether I should try to get paid out. My understanding is that no one with unlimited vacation has asked for a payout. It doesn’t make sense to retain an attorney for the potential of one month’s pay, and I don’t want to leave a month’s pay on the table! I’ve read your previous articles, and I’m still a little confused about what actually counts as “accrued” time.

Some information that may, or may not, be relevant:
* I do not live in a state with mandatory vacation payouts, but I know our policy is that hourly employees are given time earned when they leave.
* Our currently posted handbook references vacation accrual rates, with no mention of unlimited PTO (the current handbook is dated roughly a year after the unlimited PTO policy was enacted)
* I don’t explicitly see accrued time on my paystub, but our HRIS shows a paid time off balance.
* Hours are subtracted from this balance when I take time off, which is periodically topped off so that I always see around 4 or 5 weeks available.

Any advice? Should I push back?

If you’ve had unlimited vacation time (rather than accrued vacation time) the whole time you’ve been there except for your first few weeks, there’s no vacation time for them to pay out and asking won’t change that. A big part of the reason companies change to unlimited vacation time is so there’s nothing to pay out when people leave.

The fact that your handbook is outdated when it comes to this policy doesn’t change that. If you lived in a state that did require vacation payout upon leaving, it’s possible that your HRIS showing a time-off balance (which is probably just a holdover from the old system that no one has bothered to fix) could maybe give you some basis for argument — but your state law doesn’t require them to pay it out regardless, so it’s highly unlikely that they’d agree to. They’ll just tell you that you don’t accrue vacation time, per well-known company policy, and that’ll be the end of it. In a state that doesn’t require vacation payouts, a lawyer wouldn’t be able to change that even if you did want to try.

You’re not leaving money on the table because their unlimited vacation system is specifically set up to ensure it’s not there.

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