Should I Stay or Should I Go Now...

It would be hard to take them with me. Both from the perspective of legal issues with my current company... but even if I set that aside, it's unlikely any company would have openings for all 3 of our roles. If they do, it means their current situation is an absolute dumpster fire and they are getting rid of the entire global leadership structure for my function and starting over. Which I can certainly do with the two of them, but likely situations like that do not happen in isolation... it would very likely mean there are much bigger issues with the overall company.
Then what it comes down to is this - do you believe that you will be able to replicate as cohesive of a team elsewhere? And if not, does having a better boss mean finding a team that you don't work as well with?
 
My previous boss left. I got along great with her. This woman was my peer. She was elevated on an interim basis while they hired somebody from the outside. That took 6 months, and the person hired was a complete disaster. My CEO fired that person after 3 months, and elevated my current boss back to interim. After a year, he admitted to me he'd given up looking for a new replacement, as he couldn't afford another disaster like the last one. He said he needed me to make it work with her.
There it is!

She is undermining you because in her mind, you are a threat to her.

Go get some job offers (or at least some interviews and interest) and then go to her boss and say I'm trying to leave because of this loser. Hopefully the CEO will choose you. If not, at least you get a new job away from her.
 
Find a new job, but be patient about it. I had a similar situation where my boss was nice to my face and then I found out he was undermining me and my team. Caught him in numerous lies, so I had it out with him and it left us in a situation where it was quite antagonistic. I felt like I had to make a move so I did, but the job I landed in was less than ideal. I spent about a year there when a client of mine asked me to join his company on their executive team and I've been here for almost ten years and it's been the best move I've ever made. So it worked out, but it could have gone a lot worse because I was impatient with the situation.
Good perspective. It sure sounds like the OP needs to make a change, but the one thing you don’t want to do is jump at the first available new role just for the sake of getting out of the current situation. I did that earlier in my career and fortunately ended up in good situation that kept my career on track, but in hindsight I took the job primarily to get away from my old one and didn’t put in much thought into why I was picking the new role/company.

Sounds like the OP is well-connected within their industry though and probably has options/is familiar with which firms would be good landing spots. Still, I think the best thing to do in a situation like that is to start the hunt for a new job with the mentality that it will probably at least take a few months (if not longer) to find the right fit.
 
Sorry that happened to you. CEOs have a million things weighing down on their heads. When you are useful to them, they have your back. But they have to be ruthless to do their job... it's why such a high percentage of CEOs (and politicians) are sociopaths... or that's my unverified POV. I don't think my current CEO is a sociopath. He's a good guy as CEOs go. But he does not have time to waste dealing with my issues.

I completely understand where you're coming from. But if you're leaving anyway, you might as well tell him why and let him decide if your issues are worth his time. I'm guessing he would think they are.
 
Then what it comes down to is this - do you believe that you will be able to replicate as cohesive of a team elsewhere? And if not, does having a better boss mean finding a team that you don't work as well with?
It takes a lot of time to build a new team. I've been working with these two leads for 10 years now... they have both earned 3 significant promotions since I took over.
 
I do not have anything that currently looks promising. I looked into a few opportunities, but was not impressed with any of them. It will take months for me to find a new job, especially if I'm careful to make a good decision. I definitely will not leave this one until I have something lined up. I do not want the pressure of not having a job push me to accept something I should not.

I'm at an age now where I'll still have good options. But in the corporate world, age is held against you once you get past a certain age... and I'm getting close. If I change jobs and end up in a worse situation, I could easily find myself on the wrong side of the age divide and months could turn to years in the job hunt.
Got it, But you seem to have answered your own question, haha - you're staying until you can line up something else.
 
Good perspective. It sure sounds like the OP needs to make a change, but the one thing you don’t want to do is jump at the first available new role just for the sake of getting out of the current situation. I did that earlier in my career and fortunately ended up in good situation that kept my career on track, but in hindsight I took the job primarily to get away from my old one and didn’t put in much thought into why I was picking the new role/company.

Sounds like the OP is well-connected within their industry though and probably has options/is familiar with which firms would be good landing spots. Still, I think the best thing to do in a situation like that is to start the hunt for a new job with the mentality that it will probably at least take a few months (if not longer) to find the right fit.
I'm weighing this option vs. just waiting my boss out. My CFO told me last week she thinks it could be anywhere from 18 months to 3 years. It will take me at least 3 months to find something new. It could easily take 6. There are just not that many open roles for what I do at any given time. And when they do come open, companies tend to take their time and check out all their options.
 
I'm trying to decide whether to look for a new job. I can't stand my boss. Her idea of managing a team is to bring everybody together and do cheesy teambuilding exercises, then pull them aside one by one and set them against each other in a hunger games-esque fight to be in her good book.

I can mostly ignore her because my CEO told her to leave me alone and let me do my thing... but she tightly controls everything I can or can't do for the team I manage, and she holds it over my head to keep me in check... and constantly tries to undermine my team by going behind my back and telling them I'm not asking for the things she's refusing to let me do for them.

I've nearly lost the most important person on my team twice because my boss outright lied to her and said I was blocking her promotion (when it was her doing it). She's also taken lately to doing regular connects with that lead, and spending most of it saying terrible things about me... then having connects with me where she acts like we're best buds and never has a single bad thing to say about my work.

My boss has been telling me for 5 years now that she plans to retire in 2 to 3 years... I don't believe her. She loves the power, and how the rest of our team has to kiss her ass to get ahead.

I've been with the company for 18 years. I have very good relationships with my CEO and CFO. They watch over me to make sure I'm personally fine, but I can't go whining to them with he said/ she said stuff about how my boss messes around with my team.

I figure I want to work another 8 to 10 years before I retire. My company has been struggling for last 3 years. Not a reflection on my company itself, our industry is just in a weird inflection point. I am confident things will turn around... but the "when" is very much TBD still.

My CEO still takes care of me better than most, but the state of our business has cut my bonus and stock grants A LOT the last couple years. The nature of my job makes it very easy for me to change industries, so I am not trapped in a down industry. But I also believe that when things get sorted out industry wide, we will be in for a good run for 5 or 6 years where I can make up for what I've lost.

So come on and let me know...
Only you know how much you enjoy your job and are willing to tolerate your boss. I've been through this situation twice and managed to outlast my terrible bosses twice, while quietly working to undermine them. I saw it as a sort of personal challenge each time, one that I wasn't willing to lose.

My kids, who work at the same restaurant, have gone through this no less than 4 times and have outlasted their terrible bosses each time. The most recents last day is tomorrow, as a matter of fact.
 
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I completely understand where you're coming from. But if you're leaving anyway, you might as well tell him why and let him decide if your issues are worth his time. I'm guessing he would think they are.
When I have something lined up, I'll definitely have an open honest convo with him. But once I decide to go, I don't tend to look back. I've never once entertained a counteroffer...
 
Got it, But you seem to have answered your own question, haha - you're staying until you can line up something else.
Or procrastinating and hoping she leaves sooner rather than later. If I'm 100% honest, I'd rather not give this job up. Starting from scratch will mean having to work 10 to 12 hour days for 2 to 3 years until I get things working they way I have them working here. I'm at the stage now where I have the occasional busy peak of 60+ hour weeks, but I have more weeks where I can get my stuff done in <40. It was not easy to build what I have here.
 
Or procrastinating and hoping she leaves sooner rather than later. If I'm 100% honest, I'd rather not give this job up. Starting from scratch will mean having to work 10 to 12 hour days for 2 to 3 years until I get things working they way I have them working here. I'm at the stage now where I have the occasional busy peak of 60+ hour weeks, but I have more weeks where I can get my stuff done in <40. It was not easy to build what I have here.
That’s worth a lot.

When your boss was your peer, what was she, and your relationship with her, like?
 
That’s worth a lot.

When your boss was your peer, what was she, and your relationship with her, like?
She was a regional chief talent officer (head of HR). She was very protective of her region and tried to keep me from interfering. We did not have a lot of interaction. She preferred to work through my #2, who is also based in her region... she could get away with bullying my #2 into things she knew would not fly with me. We got along fine, but mostly because I only stepped in and interfered when I felt is was absolutely necessary... I'm not a control freak, so I can live with more than most.
 
When I have something lined up, I'll definitely have an open honest convo with him. But once I decide to go, I don't tend to look back. I've never once entertained a counteroffer...

I understand that. I once left a job because my boss wouldn't allow me to fire a subordinate who absolutely deserved to lose their job. She was trying to negotiate a "solution" that would allow him to stay with the company. I tossed her my keys and told her I didn't negotiate with terrorists. That may seem rash to some but this wasn't the first time something like this had occurred.
 
Counteroffer - Please stay in your current position until we get your repacement on-board and then we will fire you.
That would not be the worst problem ever... if they let me go, I get a good severance package after 18 years with the company...
 
Conventional wisdom says that if you go there will be trouble, but if you stay you will end up with twice as much trouble. Honestly the guy I heard it from said it more eloquently than I did.
 
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