A colleague is nearing retirement age, and you are curious as to when they will take the step and what they plan to get up to. Your intentions are not self-serving beyond the fact that you will miss the person when they go; and you are genuinely interested in what life holds in store for them. How can you ask them about their plans without coming across as "rushing them out the door?"
So much depends on why you are asking:
- are you worried about what you will do when they're gone?
- are you curious about a chain of promotions once their spot opens up?
- are you planning your own retirement and looking for ideas and options for what to do afterwards?
- do you just think it would be a nice conversational topic with someone you feel friendly towards?
There's a huge difference between "When will you retire?" and "What will you do when you retire?". Either one can be rude, but certainly the first is more likely to be a problem.
If your reasons for asking are both personal and positive, then you can surely ask. State your reason, then ask directly:
- I hear scuttlebutt that you might be nearing retirement age even though you don't look it. Is that true?
- Man, if you ever retire my lunch breaks are going to be so boring! Tell me that won't be for years yet.
- I just got back from a week at the cottage. Some day I'm going to retire there and have the best summers of my life. [They may just say "that sounds nice" or they may tell you their plan. Don't push if they don't pick up the hint.]
- Joe from Accounting is retiring eh? I never thought about it. Have you? [Don't do this if you're 30-40 years younger than retirement age.]
When you want information from someone, my strategy is "give before you take" - give them a piece of information, and then ask something. It gives them context so they know why you're asking and don't feel nervous that they're going to be pressured into something.
This is a tough one :P
I would personally ask them if they are planning on retiring soon. Moving around the question bothers me as a person and people being honest really helps.
Hey, how are you doing? ...
<normal conversation> ... so I have been meaning to ask you, are you planning to retire anytime soon? I would miss you when you retire.
Really just getting to the point and not trying to probe around the question would help out.
I personally used this in my life and it turned out fine. Nobody was offended or felt "rushed out the door". Sometimes not trying to go around the question is the right thing to do.