AI Prompts for Client Onboarding, Check-ins, and Retention

Review my active client relationships using recent emails, meeting notes, calendar records, project management updates, support requests, and client notes.

Score each active client as:

- Warm
- Neutral
- Cooling
- At risk

Use real signals, including:

1. Reply speed changing
2. Shorter or colder messages
3. Missed meetings
4. Unanswered questions
5. Delayed approvals
6. Payment delays
7. Reduced enthusiasm
8. Fewer proactive updates
9. Threads where I failed to respond
10. Scope or expectation tension

Show the cooling and at-risk clients first.

For each one, give me:

1. Relationship score
2. Evidence
3. Likely reason
4. Best next action
5. Draft no-agenda check-in note in my voice

Mark all drafts HOLD.

Based on everything you can access (emails, invoices, notes, meeting records, project status, payment history, and client relationship signals), tell me which one client I should personally call today.

Give me only one answer.

Include:

1. Client name
2. Why this is the highest-priority call
3. What is at stake
4. Three specific things to say on the call
5. One thing not to say
6. Whether the goal is retention, repair, upsell, collection, clarity, or appreciation

Do not give me a list of ten. Pick the one that matters most.

I need to send a difficult email and I have been avoiding it.

Situation: [late payment / price increase / saying no to scope creep / ending an engagement / pushing back a deadline / correcting a misunderstanding / refund issue / boundary issue]

Client or contact: [name]

Before drafting, read our email history, project history, invoices, contracts, and notes so you understand the relationship and context.

Then draft two versions:

1. Softer version
2. Firmer version

Both should be:

- Direct
- Warm where appropriate
- Clear
- Not over-apologetic
- Not corporate
- Not defensive
- Specific about what happens next

Tell me which version you would send and why.

Mark both drafts HOLD.

Find our best recently finished client project based on evidence in my files, emails, notes, invoices, results, testimonials, final messages, or before-and-after proof.

Pick one project.

Reconstruct the case study from the actual record.

Include:

1. Type of client or business, without naming them unless already approved
2. Where they started
3. What problem they had
4. Why they chose us
5. What we did
6. What changed
7. Proof of outcome
8. Client language or quotes where available
9. What made the work successful
10. What a similar client should learn from it

Flag any claim you cannot verify.

Draft a one-page case study.

Do not use the client's name unless I explicitly approve it.

Review the email threads, documents, forms, checklists, contracts, and project files from the last three clients we onboarded.

Reconstruct what actually happens during the first two weeks.

Identify:

1. What we send
2. What we ask for
3. What clients often forget
4. What causes delays
5. What we repeat manually
6. What expectations are unclear
7. What would make onboarding smoother

Then build an onboarding pack:

1. Welcome email
2. What-to-expect one-pager
3. Client checklist
4. Internal checklist
5. Timeline for the first two weeks
6. FAQ based on real client confusion

Write the welcome email in my voice based on real sent emails.

Mark the email HOLD until approved.