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Lessons learned from an AI initiative (without blame)

Teams closing, pausing or scaling an AI initiative.

Editable template 20 min to use Updated 2026-10-19
Vic Sol · Decision DeskEditable template · 20 min to use

Lessons learned from an AI initiative (without blame)

For the team closing, pausing or scaling an AI initiative that wants the company to learn something before everyone moves on to the next project.

When to use it

  • The pilot ended and the final report says "mixed results" without saying what changes.
  • The initiative is about to scale and nobody has written down what went wrong along the way.
  • Something was cancelled and the corridor conversation already has a culprit. This sheet is there to replace it.

The sheet

Initiative: ____________________ · Status: close / pause / scale · Session date: ____________

FieldWhat to writeIllustrative example
What we expectedThe number or result the original proposal promised, copied word for word."Quotes from 3 days to 1 in 8 weeks."
What happenedThe actual number, with a date. No adjectives."Week 8: 2.5 days. Week 12: 2 days."
Which signal we ignoredThe data point that was in plain sight before it became obvious, and when it was first seen."Week 3: only 2 of 9 reps were using the draft."
What we keepWhat worked and stays, even if the initiative changes."The quote template and the single reviewer."
What changes next timeOne concrete rule for the next initiative, not an intention."No pilot starts without a user from the area from day 1."
Who owns the changeOne named person and the date the rule takes effect."Laura (sales), from the next pilot, 1 March."

How to fill it in 20 minutes

  1. Before the session, the lead fills in "what we expected" and "what happened" from the original documents. Those two rows are not debated: they are data.
  2. In the session, each person writes in silence for four minutes which signal they think was ignored. Then they are read in a round, with no reply.
  3. Pick the signal most people saw. That is the lesson; the rest go in an appendix.
  4. "What we keep" comes before "what changes". A team that only lists mistakes stops proposing.
  5. Write "what changes" as a rule that can be checked in the next initiative, and give it an owner and a date.
  6. The most common mistake: turning the signal row into a row of people responsible. The question is which data point was in sight, not who should have seen it.

How to run the 45-minute session

  • Minutes 0–5: the facilitator reads the rules: we talk about decisions and data, not people; nobody defends themselves; whoever led the initiative listens first.
  • Minutes 5–15: data. Read the rows "what we expected" and "what happened". Correct figures, not interpretations.
  • Minutes 15–30: signals. Silent writing, round, choice of the main signal.
  • Minutes 30–40: what we keep and what changes. One rule, not five.
  • Minutes 40–45: owner and date. Without this, the sheet gets filed with the project.

The line that is almost always missing

"Which signal we ignored." Closing reviews tell what happened and what would be done differently, and skip the middle step: which data point was available and not looked at. That row is what stops the same closure from repeating under another project name.


Vic Sol · Decision Desk · vicsol.org/resources/ · Free to use with attribution. This sheet structures a conversation; it is not legal, financial or audit advice.

  1. Open the .docx in Word (or the .xlsx in Excel) or print it before the meeting.
  2. Fill the fields with the team; leave the blanks visible, they are the discussion.
  3. Close with one owner, one date and one next action. Nothing else.

Prompt

Generate this sheet for your case

Paste this prompt into ChatGPT, Claude or Gemini together with your proposal, process or policy. It reproduces the sheet with your data and flags what is missing.

Download the prompt (.md)
Act as a project director with experience closing technology initiatives, who separates data from interpretation, does not look for culprits, and turns every review into a verifiable rule for the next one.

Context I am giving you:
- Company and area: [e.g. insurer, 800 people, customer service]
- Initiative and status: [name · close / pause / scale]
- What the original proposal promised, with number and deadline: [copy word for word]
- What happened, with figures and dates: [ ]
- Milestones or tracking data I have: [week by week, if available]
- Original proposal and closing report: [paste text or write "none"]

What I need: a lessons-learned review with exactly these six fields, in this order:
1. What we expected: the promised number, unrewritten.
2. What happened: the actual number with a date, no adjectives.
3. Which signal we ignored: from the tracking data, up to three signals that were in plain sight before the final result, with the date each appeared, earliest first.
4. What we keep: what worked and should stay.
5. What changes next time: one concrete, verifiable rule for each signal in point 3, not an intention.
6. Who owns the change: one role per rule (I will add the name) and a suggested effective date.

Output format: a table with the columns Field · Content, followed by three questions the facilitator should ask in the session to confirm or discard the signals. Maximum 400 words. No introduction.

Rules:
- Do not invent figures or dates. If data is missing, write [DATA PENDING] and tell me where to look for it.
- Do not attribute the result to people or to "lack of commitment"; describe decisions, data and moments.
- Mark every interpretation as an interpretation.
- If critical information is missing, ask me at most 3 questions before answering.
- Answer in plain, direct business English, with no sales adjectives.

What to check in the answer:

  • Does each signal have a date and a data point, or did it settle for "adoption was low"?
  • Can the rules in point 5 be checked on day one of the next initiative, or are they good intentions?
  • Did it name a person as a cause? If so, ask it to rewrite that row in terms of decision and data.

If this becomes a big decision

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