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Knowledge transfer interview questions (for someone leaving or changing role)

Last updated 24 October 2026

An exit interview asks why someone is leaving. A knowledge transfer interview asks how the work actually gets done. This page has 29 questions for the second kind, grouped by topic, with follow-up prompts, an add-on for support roles, and a way to turn the answers into something the next person can use.

Free to copy and print. Works without any software. No email address needed.

Use it for a retirement, a resignation, a promotion, a move to another team, before parental leave or a planned long absence starts, or when a new manager wants to learn how the team really works. It works for people who are staying too.

How is this different from an exit interview?

Cal Poly's Offboarding Knowledge Transfer Plan makes the same split: of its interview step it says "this is not an exit interview." The reasons someone is leaving have their own questions, and this page does not cover them.

When should you run it?

Run it as soon as the change is known. The person has the most time and goodwill early on, and there is less pressure than in the last week.

• Hold it one to one, in a quiet slot, not on the last day.
• Plan for 30 to 45 minutes per session, and more sessions if needed. Do not squeeze 29 questions into one sitting.
• Do it before you write the handover document. The interview shows what the document needs to say. See the handover checklist.

If notice is short: the top 5

If you only have 20 minutes, ask the five questions marked with a star (★). These are the five that are hardest to rebuild after the person has gone. Write the answers down in the person's own words.

The questions

Ask them in order if you can. Some groups are shorter than others because the topic calls for it. Skip any that do not fit the role.

A. A normal week

1. Walk me through last Tuesday, hour by hour.
2. What do you do every day before anyone asks you to?
3. What happens monthly, quarterly or once a year that most of the team never sees?
4. Which requests do people send to you personally instead of to the team, and why you?
5. What do you check regularly to know that everything is fine?

Follow-up prompts: "What did you do that was not on your task list?" "Which of those would you do first if you only had an hour?" "Who notices if you skip it?"

B. Exceptions and edge cases

6. ★ When does the usual process not apply? Tell me about the last time.
7. Which rule doesn't fit the real cases, and what do you do instead?
8. Which cases look standard but are not, and how can you tell?
9. Which cases do you pass on to someone else instead of handling? Where is the line?
10. Tell me about the last time something went wrong. What changed afterwards?

Follow-up prompts: "What did you do in that case?" "Why that and not the standard way?" "Has it happened more than once?" "Who else knows about this?"

C. Clients and partners

11. What has been agreed with someone by phone or in conversation that is not in a contract or a system?
12. ★ Which customer or partner needs different handling, and why?
13. Which customer or partner is easiest to upset, and what upsets them?
14. Which external contacts should the next person meet before you go, and what is each one good for?
15. Which customers or partners have dates, seasons or deadlines that change how you work?

Follow-up prompts: "What is the name of that customer?" "Where is that agreement written down, if anywhere?" "What would happen if we handled them the standard way?"

D. Approvals and people

16. ★ Who has to approve what, at what amount or limit, and who do you ask when the approver is away?
17. Who do you ask informally to get something done faster, and what do you ask them?
18. Who in the company knows things about this work that you do not?
19. Tell me about a time an approval was missed. No blame: I want to know what the process didn't catch.

Follow-up prompts: "Is that written anywhere, or do you just know?" "What if that person says no?" "How long does it usually take?" "Who set that limit?"

E. Systems and workarounds

20. ★ Which system step do you do by hand because the tool gets it wrong?
21. Which spreadsheets, folders, saved searches or inboxes do you rely on that are not official?
22. Which report or number do you not trust, and what do you use instead?
23. What breaks first when it is busy, such as month end or a launch?
24. What do you do when a system is down?

Follow-up prompts: "Show me where that is." "How did you find out it was wrong?" "Who else uses that workaround?" Do not ask for passwords or logins. Ask where access is kept and who grants it.

F. What a new person gets wrong

25. ★ What do new people usually get wrong in their first month?
26. What do you wish someone had told you in your first week?
27. Which requests sound urgent but are not, and which sound minor but are not?
28. What would you check before trusting a new person to do this alone?
29. What question will the team ask three months from now that you can answer today?

Follow-up prompts: "Can you give me a recent example?" "How would they find out they got it wrong?" "What is the quickest way to put it right?"

Support role add-on

If the person works in customer support or a help desk, add these five. They are the ones an AI support agent gets wrong most visibly, because the answer lives in someone's head.

• S1. Which macros or saved replies are out of date, and what do you say instead?
• S2. Which help-centre articles are wrong, and which one does the AI agent quote wrongly?
• S3. What can you refund, credit or extend without asking, and up to what amount?
• S4. Which accounts skip the queue or get a different SLA, and who decided that?
• S5. Which ticket types should the AI agent never answer alone?

Follow-up prompts: "Show me a recent ticket where that applied." "Who would I ask if you were away?" "Is that written anywhere the agent can read?"

How should you ask them?

Ask for the last time it happened, not what usually happens.

Before you start

• Say what the notes are for. They are to help the next person, not to assess the one leaving.
• Say who will read them. Name the people.
• Say they can read and correct the notes before anyone relies on them.
• If you have a works council, check whether it wants to know before you start.

During the interview

1. Ask one question at a time. Then stop talking. Two questions in one turn get a one-part answer.
2. Ask for a recent real case. "What usually happens?" gets a policy. "Tell me about the last time" gets what really happened.
3. Listen for "usually", "normally", "it depends" and "except". Each one hides an exception. Ask when it is not usual and what happens then.
4. Get specifics. Which customer, which system, which person, which amount, which day.
5. Ask why. If the reason for a rule is not obvious, ask. The reason tells the next person when the rule stops applying.
6. Never ask for passwords, credentials or personal data about customers. If the person offers them, tell them not to share them.
7. Do not ask why they are leaving. If they raise it, listen. Do not steer to it.
8. Thank them. They are giving up time. Say what the notes will be used for.

What should you do with the answers?

Write each answer as a rule: when it applies, what to do, and why. Keep the person's exact words next to it. Write down the exception, the reason for it and the person's own words.

A filled-in answer:

• Answer in the interview: "Normally it's thirty days to return. But for the big retail accounts it's sixty, because their season ends late. Don't tell the small shops, they'll all ask."
• When: a retail account on the large-account list asks to return goods between day 31 and day 60.
• Do: accept the return. Do not offer the 60 days to other customers.
• Why: the large retail accounts' season ends late.
• In their words: "for the big retail accounts it's sixty, because their season ends late."

Then check it. Ask the person to read the notes, or have their manager do it, before anyone relies on them. A note nobody has checked is a guess with a name on it.

Can Keeplore ask these for you?

Keeplore asks questions like these as a private chat, and you can use the questions above without it. What it does:

• A private text chat of about 30 to 45 minutes. The person can pause and resume.
• It follows up when someone says "usually" or "it depends".
• Each answer becomes a rule with when, what to do and why, plus the exact quote. Rules whose quote isn't in the transcript are dropped.
• A manager approves, edits or rejects every rule.
• Your agent queries the approved rules through an API, or you export them as JSON or Markdown. Keeplore doesn't push into your systems; your agent pulls.
• The person gives consent before the interview starts.
• The app and database run in the EU (Frankfurt); interview text is processed by Anthropic in the US.
• There is a data processing agreement, and you can delete an interview and its rules in one click.
• No connections to email, Slack or calendars, on purpose.

More in how Keeplore works and security.

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Related

• Handover checklist
• Keeplore for customer support teams
• How Keeplore works