Ask farewell questions that lead past 'we will miss you.'

Easy opening questions

Begin with recall, not judgment. People answer faster when they can picture a moment.

• What is the first work moment with them that comes to mind?
• Which phrase or habit will make you think of them?
• What small thing did they reliably make better?
• Which project best captures how they worked?

Questions about impact and support

These questions invite evidence without forcing a grand answer.

• What did they make easier for other people?
• What did you learn from working with them?
• When did they make you feel supported?
• What do you do differently because of them?

Questions about the team

Team-level prompts show the effect one person may not have been able to see from inside their role.

• What will the team continue doing because they introduced it?
• What will feel different in an ordinary week?
• Who became more confident because they made room for them?
• What standard did they quietly raise?

Light questions with a real answer

Humor works best when it stays tied to affection and shared context.

• Which harmless habit of theirs should the team officially adopt?
• What object, snack, or meeting belongs in their office museum?
• Which story can the whole group laugh about without embarrassing anyone?

Generic versus specific

Generic: 'Describe Jamie in three words.' Specific: 'Which ordinary moment shows what Jamie was like as a colleague?' The second prompt produces something the recipient can picture.