TL;DR — A retirement video benefits from a longer time horizon than a standard farewell — the questions should reach back across a whole career, not just the last few months. Ask what they're proud of and what they'll do next, not just "we'll miss you".
- Ask about the whole career, not just recent memory.
- Include questions about what retirement looks like for them, if they're open about it.
- Give longer-tenured colleagues more room to speak than a standard farewell.
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Why a retirement video is a different brief from a standard farewell
Someone leaving for another job is usually thought of in terms of the immediate team and recent projects. Someone retiring has often been there far longer, has worked with people who have since moved on themselves, and the moment carries more weight than a typical goodbye. The questions should reflect that longer arc.
Questions that reach across a career
- "What are you most proud of from your time here?"
- "What's changed the most since you started?"
- "Who do you wish could be here to see you retire?"
- "What's one piece of advice you'd give to someone just starting out?"
- "What will you miss, and what definitely won't you miss?"
Questions about what comes next
If the person is open about their plans, a question or two about retirement itself adds warmth without being intrusive: "what are you looking forward to first?" or "any big plans for the first week?" tends to get a genuine, often funny answer.
Collecting from former colleagues, not just the current team
Someone with a long tenure has often outlasted several waves of colleagues who have since left the company. Consider sending the link to a few former teammates as well as the current team — they may have memories nobody currently there can offer.
Frequently asked questions
Should we ask about pension or financial plans?
No — keep questions to career and personal reflections; financial details aren't an appropriate topic for a group video.
How long should a retirement video be compared to a standard farewell?
It can run longer given the number of years typically being reflected on — see How Long Should a Farewell Video Be? for the trade-offs as contributor count grows.
Can we invite family members to contribute?
Some teams do, with the retiree's knowledge — it works well as a surprise element if the rest of the video isn't a surprise.