TL;DR — An open invitation to "say a few words" produces short, generic clips. A specific prompt produces a message worth keeping. Here are 25 prompts, grouped by what they ask for, plus guidance on sending the right one to the right person.
- One prompt per request works better than offering several to choose from.
- Memory-based prompts outperform compliment-based ones almost every time.
- Match the prompt to how well the person knew the leaver.
On this page
Memory prompts
These ask for one specific moment, not a general impression — the easiest way to avoid a generic message.
- "What's one memory with them that's stuck with you?"
- "Tell them about a time they helped you out."
- "What's something funny that happened that only makes sense if you were there?"
- "Describe the first time you worked together."
- "What's a small thing they did that you never told them mattered?"
Gratitude prompts
- "What did you learn from them?"
- "What are you grateful they taught you, directly or by example?"
- "How did working with them change how you do your job?"
- "What would you thank them for if you only had one sentence?"
- "What will you miss most about having them around?"
Forward-looking prompts
- "What do you hope for them next?"
- "What are you confident they'll do well wherever they land?"
- "If you had one piece of advice for their next chapter, what would it be?"
- "What won't change about your friendship now that you don't work together?"
Lighter, funnier prompts
- "What's something ridiculous only your team will understand?"
- "What are they leaving behind that no one else can fill?"
- "What's the most 'them' thing they ever did at work?"
- "What's a running joke you'll keep telling after they're gone?"
- "What do you want to go on record complaining about, now that they're leaving?"
Prompts for a manager or someone senior
- "What impact did they have on the team that others might not see?"
- "What decision of theirs are you most grateful for?"
- "How did they make people around them better?"
Prompts for a close teammate
- "What will Monday mornings be like without them?"
- "What's something you two always did that you'll have to do solo now?"
Send the prompt with the request, not after
Set the prompt once in your campaign and everyone sees it the moment they open the link — so you're not emailing it separately to each person or hoping they scroll back to find it.
Start freeFrequently asked questions
Should I offer multiple prompts to choose from?
One works better. A choice of prompts creates hesitation; a single specific prompt gets people recording faster.
What if the prompt doesn't fit how I knew the person?
Swap it for one from a different category above — the point is specificity, not following a script exactly.
Does the prompt need to match across the whole team?
No. Different contributors can answer different prompts in the same campaign; the reel still holds together on the shared subject.