Follow Up

Follow-Up Skill

Detects stalled items and communication gaps, then drafts follow-up messages in your voice.

What It Checks

1. Waiting On Items Past Interval

Look through all project files ~/ops/projects/*.md:

For each waiting_on entry, check:

waiting_on:
  - what: Design assets from client
    who: Acme Corp
    since: 2026-03-10
    follow_up_interval_days: 7
    last_follow_up: 2026-03-15

Is it overdue? If (today - last_follow_up) > follow_up_interval_days, it's overdue.

Example:

• Since: March 10
• Interval: 7 days
• Last follow-up: March 15
• Today: March 19
• Days since last follow-up: 4 days
• Status: Not overdue yet, but close (follow up on March 22)

2. No Communication in 7+ Days

Check all projects for communication_log (if it exists):

communication_log:
  - date: 2026-03-12
    type: email
    to: jane@acme.com
    subject: "Phase 1 status update"

If project is active and last communication was 7+ days ago → suggest follow-up.

3. Milestones Near Completion

Check for milestones that are in "almost done" status:

contract:
  milestones:
    - name: Phase 1
      status: in-progress
      deliverables:
        - Feature A: complete
        - Feature B: complete
        - Feature C: 95% complete

If all deliverables are done or nearly done → prepare for delivery communication.

Report Format

Display what needs follow-up:

FOLLOW-UP ITEMS

[Project A] – Acme Corp
  Status: Awaiting design assets
  Since: March 10 (9 days)
  Last follow-up: March 15 (4 days ago)
  Action: Send friendly follow-up request

[Project B] – Example Client
  Status: No communication in 7 days
  Last contact: March 12 (7 days ago)
  Action: Send status check-in

[Project C] – Other Corp
  Status: Phase 1 nearly complete
  Complete: 95%
  Action: Prepare delivery notification

Draft Messages

For each item needing follow-up, draft a message using the writer agent:

Invoke writer agent with:
- Project name and client
- Current status
- What you're asking for
- Timeline if relevant
- Tone: friendly, professional, not pushy

Agent reads:
- ~/business/memory/clients.md (client communication preference)
- ~/ops/templates/voice-guide.md (your voice)
- Drafted message should match your writing style

Message Types

Waiting on deliverable:

Hi [Contact],

Quick check-in on the [Deliverable] we discussed—we're ready to integrate
your [deliverable type] into Phase 1 as soon as you can share it.

If there's anything blocking this on your end, just let me know. I'm happy
to adjust the timeline if needed.

Best,
[Your name]

Status check-in (no recent communication):

Hi [Contact],

Hope things are going well on your end. Just wanted to touch base on
[Project Name]—where we stand on [current phase/milestone].

Happy to jump on a quick call if you have questions or want to discuss
next steps.

Best,
[Your name]

Delivery notification (milestone nearly complete):

Hi [Contact],

Great news—Phase [X] is nearly complete. We're on track for delivery on
[target date].

I'll have [specific deliverables] ready for your review by [date]. When
you've had a chance to test, let's schedule a brief walkthrough.

Best,
[Your name]

Save Drafts

Save drafted messages to a follow-up folder:

mkdir -p ~/business/communications/follow-ups/
# File location: ~/business/communications/follow-ups/YYYY-MM-DD-{project-name}.md

Include:

• Who you're following up with
• Current status
• What you're asking
• Drafted message
• When to send (immediate, or after [date])

Update Project File

After sending, update the project ops file:

waiting_on:
  - what: Design assets
    who: Acme Corp
    since: 2026-03-10
    follow_up_interval_days: 7
    last_follow_up: 2026-03-19  # Updated today
    status: follow-up-sent

And add to communication_log:

communication_log:
  - date: 2026-03-19
    type: email
    to: jane@acme.com
    subject: "Check-in: Design assets for Phase 1"
    status: awaiting-response

Conversation Flow

This skill should:

1. Report what's overdue
2. Ask if each follow-up is still needed
   • "Should we still wait on the design assets, or have they changed their timeline?"
   • "Is Project B still active, or should we archive it?"
3. Draft messages for items you confirm
4. Ask if you want to send now or queue them
5. Save drafts and update project files

Let you have control. Don't auto-send messages. Draft, review, then you send.

Follow-Up Cadence

Suggested intervals by situation:

Update follow_up_interval_days in your project files to match your cadence preference.

When NOT to Follow Up

Skip follow-up if:

• Client explicitly said "we'll reach out when ready" (respect their timeline)
• You're waiting on third party (API provider, etc.) and follow-up won't help
• It's a passive waiting situation (their decision, not blocking you)
• Item is marked "blocked indefinitely" (acknowledge reality)

Update project file with explicit status instead:

waiting_on:
  - what: API documentation from Stripe
    who: Stripe (third-party)
    since: 2026-03-01
    status: blocked-on-vendor
    note: Waiting for Stripe to publish docs; not actionable on our end

Revenue-Weighted Follow-Up

Prioritize follow-ups that move revenue:

1. Highest priority: Waiting on client approval to bill a completed milestone
2. High priority: Waiting on deliverable that unblocks your milestone
3. Medium priority: Status check-in on active project
4. Lower priority: Checking on project on hold or back-burner

The skill should surface revenue-blocking items first.

Reads:

• ~/ops/projects/*.md (all project ops files, especially waiting_on sections)
• ~/business/memory/clients.md (client communication preferences)
• ~/ops/templates/voice-guide.md (your voice)

Writes:

• ~/business/communications/follow-ups/ (drafted messages)
• Updates ~/ops/projects/*.md (last_follow_up date, status)

Calls: writer agent (to draft messages in your voice)

Scope: Detection + drafting. You handle sending.

Cadence: Run manually as needed, or could be called as part of daily standup to surface overdue items.