100 handover questions to answer before someone leaves a role

By Peter Varga · Updated October 24, 2026 · Magyarul

Most handover documents list procedures. Procedures are rarely what goes wrong. What goes wrong is the supplier contact nobody knew about, the promise made in a hallway, the report that has been quietly wrong for a year. Answer these questions for the role, not for the person, and the successor or the colleague covering for you starts from the work instead of from scratch.

Jump to: people · commitments · rhythms · systems · decisions · risks · temporary cover · permanent handover

Who does this role depend on?

Start here, because the people outside your own team are what a handover most often leaves out.

1. Who will contact your stand-in in the next month, and about what?
2. Who should your stand-in contact first if something goes wrong, and how do they reach that person outside office hours?
3. Which people outside your team do you depend on to get your work done?
4. Who at each key supplier or partner actually answers, as opposed to who is officially listed?
5. Which internal teams do you need something from regularly, and who in each team gets it done?
6. Who has authority to approve what you cannot approve yourself?
7. Whose sign-off is needed before anything you produce goes out?
8. Who knows the history of your work almost as well as you do?
9. Which relationships need a personal introduction rather than an email address?
10. Who expects to hear from you regularly, and how often?
11. Who tends to escalate quickly, and what calms them down?
12. Which contacts prefer a phone call over email, or the other way round?
13. Who is new in their role and still relies on you for context?
14. Who used to do this role before you, and are they still reachable?
15. Who do you go to for advice when you are unsure?
16. Are there people your stand-in should be careful with, and why?

A role record lists these people from the work itself, including the cross-team contacts no one remembers to name.

What have you promised, and to whom?

17. What is due in the next four weeks, and to whom?
18. What have you promised that is not written down anywhere?
19. Which of your open items block someone else's work?
20. What are you waiting on from others, and since when?
21. Which promises were made verbally, in a meeting or a hallway?
22. What prices, discounts or exceptions have you agreed to that are not in the system yet?
23. Which deadlines are firm, and which are softer than they look?
24. What did you trade to get a commitment from someone else?
25. Which tasks are half finished, and where exactly did you stop?
26. What would embarrass the team if it were forgotten for a month?
27. Which commitments can safely be postponed, and who needs to be told?
28. What have you said you would look into but have not started?
29. Which threads are waiting for your reply right now?
30. What are you quietly expected to do that is not in your job description?

What happens on a schedule?

31. Which meetings do you run, and which can be cancelled while you are away?
32. What recurring reports or deliveries are due during the handover period?
33. What happens every day that would be noticed within a day if it stopped?
34. What happens at month end, quarter end, or year end, and what does it need from you?
35. Which renewals, contract dates or licences expire in the next six months?
36. Which seasonal peaks does this role go through, and when is the next one?
37. Which recurring meetings matter, and which are habit?
38. What prep do you do before each recurring meeting?
39. Which automatic jobs, reminders or scheduled runs depend on you?
40. What do you check first thing each morning, and why?
41. Which audits, reviews or inspections are coming up?
42. What should happen in your inbox while you are gone, and who watches it?

Which systems does this role touch?

43. Which systems does your stand-in need access to, and is that access already granted?
44. Where are the files, folders and shared drives the role works from?
45. Which accounts or licences are in your personal name and need transferring?
46. Which reports are wrong, and how do you correct for them?
47. Which workarounds do you use that nobody else knows about?
48. Which spreadsheets do you maintain by hand, and what feeds them?
49. Where do the numbers you report actually come from?
50. What breaks most often, and how do you fix it?
51. Who is the real expert for each system you depend on?
52. Which passwords, tokens or keys will need resetting when you leave, and who handles it?
53. Which tools do you use that IT does not know about?
54. What would you automate if you had the time?
55. Which integrations or data feeds do you watch, and what does it look like when they fail?
56. Which documents are the source of truth, and which are outdated copies?

This group is where memory fails most. The record shows which systems the role actually uses, not which ones the access list says it has.

Which decisions, and why?

57. Which decisions are in flight right now, and what are the options?
58. What is your current position on each, and why?
59. Which decisions can your stand-in make alone?
60. Which decisions must wait for you, or go to someone else?
61. What did you decide recently that might look strange without the context?
62. Which past decisions keep being questioned, and what is the answer?
63. What have you tried before that did not work?
64. Which rules do you follow that are not written anywhere?
65. Where do you deliberately break the official process, and why?
66. What do you say no to, and how?
67. Which trade-offs do you make without noticing anymore?
68. What does "good enough" look like for the routine work?
69. Which requests look urgent but are not?
70. What would you do differently if you started this role again?

What could go wrong?

71. What are the three things most likely to go wrong while you are away?
72. What is the worst thing that could happen, and what is the first step if it does?
73. Which customer or partner relationship is currently fragile?
74. Which problem has been quietly growing and has not been raised yet?
75. Where does the role depend on a single person, including you?
76. What compliance or legal obligations sit with this role?
77. Which mistakes are easy to make here, and how do you avoid them?
78. What would a new person almost certainly get wrong in their first week?
79. What has gone wrong before, and what was learned?
80. Where is the money in this role: what costs money if it is done badly?
81. Which external dates are fixed by law or contract?
82. Who should hear bad news first, and how?

For a temporary cover: leave, sick leave, a sabbatical

The cover does not need the whole history. They need to know what will happen while you are away and how far their authority goes.

83. What exactly is your stand-in responsible for, and what is explicitly not theirs?
84. Which decisions can they make without you, and up to what amount or risk?
85. May they contact you, how, and for what?
86. What can simply wait until you are back?
87. Who should be told that someone is covering, and who should not be bothered?
88. What does a good outcome of the cover period look like to you?
89. How should they hand the work back, and in what form?
90. Which of your plans should they not change while you are away?

For a permanent handover: retirement, resignation, succession

A successor inherits everything above plus the role's history. These questions are worth asking months before the last day, while the person is still doing the work.

91. Why is the role set up the way it is, and what history explains it?
92. Which relationships should you personally hand over in a meeting, not by email?
93. What did you build that nobody else fully understands?
94. Which unfinished projects should continue, and which should quietly stop?
95. What would you tell your successor in the first conversation, if you only had ten minutes?
96. Which of your habits should the successor keep, and which should they drop?
97. Who could the successor ask once you are gone?
98. How has the role changed over the years, and where is it heading?
99. What does the role look like when it is going well, from the outside?
100. What do you wish someone had told you on your first day?

How long does a good handover take?

Longer than people plan for. Answering these questions from memory takes days, and the answers still miss what the person does without noticing. That is the gap Understudy is built for: it reconstructs the role from the work itself, so most of the answers are drafted before anyone sits down to write. The handover document, training material and job description are generated from that record. The record belongs to the person whose role it is, and it maps the work, not the worker. You can see a full example on fictional data in the live demo, or read more on capturing a retiring expert's knowledge.

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