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Check in with a long-standing client before they drift

Your oldest client has gone quiet and you only notice when they've moved to someone else. Get a check-in that spots problems early and shows you care.

Updated 17 Oct 2026

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The prompt · ChatGPT

Help me check in with a long-standing client before they drift.

The client: [who, how long with me]
The work I do for them: [details]
Warning signs, if any: [e.g. fewer orders, slower replies, new manager]
What's changed recently: [details]

If something essential is missing, ask me 1 or 2 short questions first. Wait for my answers.

Then:
1. A short check-in message asking for a quick catch-up.
2. 5 questions for a short review call.
3. How to respond if they raise a problem, and what to offer.
4. A reminder to do this every few months.

Genuine, not salesy, UK English.

Stay in this ChatGPT chat. Do not turn on apps or connectors, and do not use memory from another chat.

A short example

Fill the blanks, then paste. who, how long with me: a short note you already have. details: a short note you already have. Leave the rest of the prompt as written.

The prompt · Claude

Help me check in with a long-standing client before they drift.

The client: [who, how long with me]
The work I do for them: [details]
Warning signs, if any: [e.g. fewer orders, slower replies, new manager]
What's changed recently: [details]

If something essential is missing, ask me 1 or 2 short questions first. Wait for my answers.

Then:
1. A short check-in message asking for a quick catch-up.
2. 5 questions for a short review call.
3. How to respond if they raise a problem, and what to offer.
4. A reminder to do this every few months.

Genuine, not salesy, UK English.

Stay in this Claude chat. Do not use a connector, and do not open a project that already holds someone else's files.

A short example

Fill the blanks, then paste. who, how long with me: a short note you already have. details: a short note you already have. Leave the rest of the prompt as written.

1

You describe the client, the work you do and any warning signs.

2

The assistant asks what's changed recently on either side.

3

You get a check-in message, questions for a short review call and a plan for what you hear.

What happens

Use Claude to check in with a long-standing client before they drift

Your oldest client has gone quiet and you only notice when they've moved to someone else. Get a check-in that spots problems early and shows you care.

Tools

Paste the prompt, fill the blanks, copy the draft.

  • Claude — required. Drafts from the text you paste. Nothing is sent.

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