Timing of retirement discussion with boss

Trying to benefit with the free travel seems kind of petty to me. Tell them your retirement plans and leave on the best terms possible. You will feel better about yourself.

I worked with a number of people who took a "farewell tour" before leaving. Many people, including me, lost respect for every one of them.....
Spend the shareholders money as you would spend your own.
 
It seems unethical to me to go on the trips, then announce that I'm leaving. Also doesn't seem right that I announce it a few days before the trip (as I currently have planned), as I'll likely have to purchase flights in the late June/early July timeframe, and it's probably about $10K all in. Plus, I will have speaking roles at these meetings.


I know it feels like it is ethical but I have learned first hand that it is all business. Once I tried to think for a greater good of a company and I was shown the door 2 weeks early. I would advise to only look out for your interests in this case because I can assure you that the company would do the same.
 
I wouldn't do anything to risk your Sept stock vesting. Not sure what constitutes risky in your situation but I'd personally likely look at retiring right before the holidays. That way, you get the trip, you get the vesting, you still provide great work for them and you have your holidays to look forward to without work. I find it curious that you view going on this work trip as "wrong" if you are, indeed, working and providing a service to your company. It's okay that this work will be a global trip. I can just as easily see another person in your situation lamenting because he/she wants to get out of "having to go" on that business trip. We all tend to view the world through our own lenses and assume that everyone else sees it the same way. You sound like a conscientious and ethical kind of person...I'm guessing they know that about you and that you have a reputation for being so. You'll figure out what's right for you. But I do hope you'll consider the benefit you are providing the company by going on that trip.
 
You're right that is a unique situation. As much as I'd like to do the same (go on a farewell tour on their dime) if I did, I think I'd wait till the start of next year to announce. Put a quarter, and a holiday, between the trips and the announcement. Come back first week of Jan and announce would be my vote.

Too soon before and the your role and the trips will be yanked for you, even if the tickets are purchased. You'll be off the agenda, and off the trip, even if you are staying through September. Which would make a miserable last quarter to work.

I wouldn't worry about the fiscal planning, that's the kind of thing that's always there.

I mean sure, you could do plan A, go do the trips, announce two weeks after you get back...and as much as I'm in the "little notice possible" and "they don't owe you anything" camp, yeah...it's kinda cheesy that way.

Unless you are bound and determined that you don't want to stay a couple months more, I like this idea of announcing about a month after the trip (so I guess that would be mid-October) that you will be leaving at then end of December. If they say, so sorry you need to leave now... then so what? Even better.

There will always be grand plans for the future that you will be a central part of and if that is a constraint then you would never retire.

By announcing a December retirement after the trip you are both appearing gracious in giving them a lot of time and giving them a choice... in fact you can even privately indicate that if they prefer that you leave earlier than December then you are ok with that too but that you will not be around for 2023.

If they mushroom you after you announce you can always then tell them that you don't like playing mushroom and will be leaving earlier.
 
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what the last two posts said.

wait until at least October to announce your target date of mid-December or end of year.

just understand they may escort you out as soon as you announce, though.
 
Don't breathe a word until your stock is vested.

After that snoop around to see if there is a succession plan. If your position is included discretely discuss the succession plan with your boss. If s/he inquires 'why the interest' you can say that given your age you want to have your probable successor prepared for the possible transition of your responsibilities. That should be enough for your manager to start thinking about ongoing projects.

Need I add that you should take advantage of preventive care offered by your corporate health insurance.
 
It certainly sounds like you are flexible and on the fence about when to tell them. I would wait until after the trip. Let the trip be the excuse that made you decide. If your boss is going on the same trip, maybe bring it up over drinks in the later half of the trip.

Vested stock, bonuses and 1 additional month of medical coverage can be lost depending on the day you choose is your last. Plan wisely. This is your time.
 
2 items -

1
I would not say anything until all is aligned- stock invested, etc. what if stock does not invest - due to market conditions. Are you 100% sure - and any stock market conditions or other situation won’t change your mind? Until you are 100%, and everything is completely in place - don’t inform - things can change.


2
This is business. You mentioned this is a large employer. Have you heard of large employers letting people go without notice? Perhaps right after this kind of trip - and not even think about it?

I think you’re thinking too highly of employer - as if it is family. As a big business, they can and do what they want, as they want - and you are an “at will” employee - that can be changed on a whim.
 
2 items -

1
I would not say anything until all is aligned- stock invested, etc. what if stock does not invest - due to market conditions. Are you 100% sure - and any stock market conditions or other situation won’t change your mind? Until you are 100%, and everything is completely in place - don’t inform - things can change.


2
This is business. You mentioned this is a large employer. Have you heard of large employers letting people go without notice? Perhaps right after this kind of trip - and not even think about it?

I think you’re thinking too highly of employer - as if it is family. As a big business, they can and do what they want, as they want - and you are an “at will” employee - that can be changed on a whim.

+1
Do the work, go on the trips, be as useful as possible, see how you feel when you get back.

In addition to the "walk you out the door" risk, for all you know, you will be energized by the trips and want to keep working for a bit, the market could tell you you need to keep working, your company could be doing layoffs and have a juicy severance package, etc. The future is unknown, don't put yourself in a position where you have no options.
 
It certainly sounds like you are flexible and on the fence about when to tell them. I would wait until after the trip. Let the trip be the excuse that made you decide. If your boss is going on the same trip, maybe bring it up over drinks in the later half of the trip.

Vested stock, bonuses and 1 additional month of medical coverage can be lost depending on the day you choose is your last. Plan wisely. This is your time.

This is not a bad idea. Boss will be there, and there will definitely be time to discuss on the trip, even if it's over a glass of wine or a walk to the meeting location. I have reconsidered bringing it up now (or before stock vesting), even in passing. Can't put that genie back in the bottle.

There is also the chance that the trip doesn't happen, which makes this far easier.

Oh, and Exchme, I have thought about the severance package thing. While unlikely for our company at this time, anything can happen, and that would be the ultimate gift.

And I have no allegiance to the company - I know they will be perfectly fine without me.
 
Wow, it sounds like some companies out there just send employees on vacations upon request! I've never heard of this "free travel" thing before! When we have work travel, we're working to benefit our clients, who have a yearly budget for attending and working and/or speaking at conferences. The company and the client are getting a benefit out of it.

So I wouldn't have an issue with a work trip right before my retirement, since it would still have the same value for my employer and client that my other trips did. The only things that I would think might be even questionable would be training trips or meeting new clients, since those could lose some of their value if I left immediately afterwards, although that is hard to quantify, it depends on the situation. Even then, it's a question of whether I am ready to take the risk of being walked out the door early or not.

Luckily, I work for an employer that sees fostering employee trust and well-being as important, but I expect that's more the exception than the rule.
 
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Wow, it sounds like some companies out there just send employees on vacations upon request! I've never heard of this "free travel" thing before! When we have work travel, we're working to benefit our clients, who have a yearly budget for attending and working and/or speaking at conferences. The company and the client are getting a benefit out of it.

So I wouldn't have an issue with a work trip right before my retirement, since it would still have the same value for my employer and client that my other trips did. The only things that I would think might be even questionable would be training trips or meeting new clients, since those could lose some of their value if I left immediately afterwards, although that is hard to quantify, it depends on the situation. Even then, it's a question of whether I am ready to take the risk of being walked out the door early or not.

Luckily, I work for an employer that sees fostering employee trust and well-being as important, but I expect that's more the exception than the rule.

Haha. No, it’s most definitely not a vacation, although I am allowed (at my expense of course) to take a side trip on the weekend to a place of my choosing as long as I can be where I need to be in time. It’s an internal training meeting, so my colleagues will definitely benefit from me being there (and doing some of the training). But if my employer requires me to do business travel, they pay for it (they do not expect the employee to pay). And I see nothing wrong with going a day early on a long international trip to acclimate to the time zone. If that means I see a few local attractions, then good for me.

And like you, I do work for an employer who sees the importance in trust and well-being.

Walking people out the door isn’t really a thing here unless you do something really bad (HR things, stealing from the company) or you go to a competitor. Then it is adios in a manner of minutes. In fact, as a manager, I would have a real hard time if I did that with an employee who didn’t hit any of those triggers.
 
How much notice would your boss give you if the company decided that it not longer needed your services?

I would say nothing. At worst...have your stock options vested, go on those trips. Who knows, in between the company could decide on downsizing or an early retirement package.
 
I was a VP at mega-corp. 25 yrs of svc. Gave 3 months notice following key vesting based on exiting before big decisions. My boss, CFO, was in denial and didn’t tell anyone for 9 weeks. Thus, publicly it looked like I gave 3 weeks notice. I felt like **** traveling world and looking friends/direct & indirect reports in the eye not being able to say something, while I knew I was leaving. People who knew me really well, trusted it was my decision. Most others thought I got the boot. My only regret.

You never know how a boss will handle the situation. It’s the one time you need to protect your own interests and it still may not go how you want.
 
Always look at it from the other side. If the company decided that they were going to downsize while you were on this trip, or while on your own vacation time, do you believe they would have any issue morally or ethically about giving you your pink slip the moment you returned on Monday morning? Absolutely not.

This actually happened to a co-worker of mine. Worse. While he was in Europe on a company trip, they laid off his entire group. Including him. He had put the airfare on his personal credit card expecting to get reimbursed when he got back and turned in his expense report. They NEVER reimbursed him.
 
First and foremost, I would not have any discussion about retiring until the stock vesting occurs. As said above, you could get walked out the door the day you announce and lose out on the stock.

I would probably do as Aerides suggests, and put in another quarter. Or maybe announce end of November for an end of year departure.

If the stock vesting was not in play, I would probably tell my boss soon to see if he wants to replace you on the trip. Or, maybe, have you take your replacement with you for a meet and greet. But I would only do this if I was prepared to be walked out the door that day.

You're right, but I always think that seems very petty on an employer's part, especially in reference to the bolded part. This is especially when it's due to a retirement and not someone being walked out because they did something awful, and they treat it as some kind of morbid betrayal. Huh?

It always seems petty when the same ones who would lay someone off at the drop of a hat but then gaslight an employee who was upset by that with a pat on the head and a "it's just business" dismissal.

Okay, rant over.
 
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Only Give 2 to 4 weeks notice. There will always be more commitments and it will never be the right time. My BIL put in several extra years becuase there was always one last project to finish. Remember they will not hesitate to send you out the door if they need to cut costs.
 
Every situation is different. The guy I'm currently reporting to just became part of our organization earlier this year. I've known and trusted him for years, however. During my first meeting with him in his new role he asked me what my timeline might be, which wasn't a surprise since we both had been having retirement discussions in the previous year before he took on the role in our organization.

I was honest with him and told him it was at most a year, preferably closer to 6 months. It was a good discussion and I offered to stay as long as needed (within reason) to help find my replacement and get the individual trained. Both he and the executive he reports to agreed with my proposal. The majority of my team is in Europe, so I will have at least one more trip there with my replacement as part of the handover. Pre-Covid, my trips there were once per quarter but I haven't done that trip since December 2019. So maybe more trips depending on how long it takes to find my replacement, which is proving to be a difficult task. As Liam Neeson said in the movie "Taken", "...what I do have are a very particular set of skills, skills I have acquired over a very long career..."

For 2022, all RSU's for this year vested and have been sold. Corporate bonus has paid out. 401K and HSA contributions were front loaded. So for now, it's just a paycheck and quarterly ESPP and an indefinite end date. That's actually OK by me with inflation being what it is and a good likelihood of recession around the corner and each month I'm here means I don't need to make an expensive Cobra payment.

While I don't have immediate, pre-planned scheduled activities coming up post-retirement, I don't want this to go on for too long. Regardless, so far this has been a win-win for everybody. And this definitely wouldn't have worked had I been reporting to somebody else instead.

Cheers,
Big-Papa
 
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This actually happened to a co-worker of mine. Worse. While he was in Europe on a company trip, they laid off his entire group. Including him. He had put the airfare on his personal credit card expecting to get reimbursed when he got back and turned in his expense report. They NEVER reimbursed him.

Bush league. Why didn't he sue them? I would have.
 
Walking people out the door isn’t really a thing here unless you do something really bad (HR things, stealing from the company) or you go to a competitor. Then it is adios in a manner of minutes. In fact, as a manager, I would have a real hard time if I did that with an employee who didn’t hit any of those triggers.

My Mega was the same, and while being walked out is a low possibility, it's the other stuff:

Trip yanked, but you stay till the end date with your responsibilities slowly stripped. You get replaced on invites because your boss starts saying "get so-and-so" instead. You hear about important decisions getting made when you used to be at that table. People look past you instead of saying hello. Dead man walking, but no one really tells you.

Your end date gets moved up, before your vest, just a few days, just enough to sting.

You might not get walked out the door, but the slow, painful, dignity diminishing things companies can do might wish you were.
 
I say talk to your boss now. If you do the big trip then leave your legacy will be the a-hole who took the big trip and left us high and dry. I would think if you express your commitment to help keep critical initiatives moving forward during your final months it will be greatly appreciated. Maybe your boss will send you on the trip anyway. But don’t burn bridges.
 
Going to the business trip is OK, as long as you have your own hotel room. Now days, corps are asking to share the room with one or two co-workers, to reduce the cost. I resigned from my previous employer due to this reason among others.
 
Late to the thread, but.....Many employers have an actual corporate (or individual employee contract) policy on giving notice, and a few even have specific rules for certain grades (directors, VPs, etc.). I would follow those rules/guidelines/contracts closely, including providing timely written notice when required. Vesting rules often include some clause about being/remaining in 'good standing' (or something similar), and violating notice policies could potentially affect that.
I retired twice. My advice is to remember this is BUSINESS. Giving notice early WILL make you a 'lame duck', possibly even persona-non-grata, as soon as you give even informal notice. Regardless of how positive a relationship you believe you have with your boss, offense may be taken by that boss or others along the chain of command no matter how you handle things. Adhering strictly to written corporate policies is taking the 'high road', at least 'officially'. Giving notice significantly earlier is a two-edged sword. Good luck whatever you decide!
 
Go on the trip. As long as you don’t plan on working or getting a reference from your company - do it.
After you get back from the trip - sit down with your boss - and have a heart to heart saying “I like where the company is going - but after talking to everyone on the trip - I don’t think I can be part of the journey - it’s time for me to leave - I’m thinking of October XX as my last day”
 
You should give notice based on what’s typical for your office. I gave 4 months notice, and for the last 3 months worked 1/2 time for 1/2 pay. Collected a nice last final check with nearly 4 weeks of unused vacation.
 
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