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Skills/Deliver and keep clients/Client activation check-in
Customer Success1 installs

Client activation check-in

Use this skill before a check-in with a client who has signed but whose work is not yet live with the people it was built for, when the call is about to become another status update. Produces a prep card: the one milestone this call exists to move, where they actually are against it, what is blocking it, and the agenda to send. Also use for "prep my check-in with [client]", "they signed but nothing's happening", "client call prep", "onboarding call".

Bailey DarlingBailey DarlingCo-Founder, Gia
Say something like
“prep my check-in with [client]”“they signed but nothing's happening”“client call prep”“onboarding call”
onboardingactivationclient-managementretentioncheck-ins
SKILL.mdView on GitHub

Applies between signing and the work being in live use. Produces a one-page prep card built around a single milestone, and a short agenda the client sees before the call.

The play

  1. Name the one milestone this engagement is working toward, in the client's terms, and keep it the same across every check-in until it is reached. One milestone, not a list. A check-in with three goals is a status update, and status updates are how an engagement drifts for a quarter.
  2. Separate delivered from in use. These are two different states and conflating them is the most expensive mistake in client work: a thing can be finished, signed off, invoiced, and used by nobody. The two-stage model and how to tell which stage a client is in are in references/activation-stages.md.
  3. Pull the context from where the work actually happens before opening any system of record. A shared channel with the client holds more signal than a CRM field, because it is written by the people doing the work. What to look for is in references/prep-card.md.
  4. Establish the gap: what is true today against what the milestone requires. One sentence. If it cannot be written, the milestone is too vague to drive a call.
  5. Identify the blocker and who owns it. Branch by who:
    • Blocked on the firm: the check-in is an apology and a date. Fix it before the call if the fix is hours.
    • Blocked on the client, and they know: the call is about removing the obstacle, not about restating the deadline.
    • Blocked on the client, and they do not know they are blocking: the hardest case. Name it plainly and early in the call, not at minute fifty.
    • Blocked on a third party: the firm chases it, not the client. This is service, and it is cheap to provide.
    • Not blocked, just not prioritised: the real finding. Something changed in their world, and the call is about whether this still matters.
  6. Write the agenda the client gets beforehand. Three lines, one of them the milestone. The patterns are in references/prep-card.md. An agenda sent in advance changes who prepares for the call.
  7. End with one commitment from each side, each with a name and a date. A check-in that ends with only the firm owing something has not moved the client at all.
  8. Record what happened and the new gap, so the next card starts from it rather than from memory.

What good looks like

  • First thing I check that most people skip: whether anyone outside the client's own team has touched the work yet. Internal approval feels like progress and is not; the work is not real until the people it was built for are using it.
  • The mediocre version: a call that opens with "how's everything going", receives "good, we've been slammed", and ends with the firm promising to follow up. It is pleasant, it costs an hour, and the engagement is in exactly the same place.
  • I know the prep is right when the first question of the call references something specific they said or did since last time.
  • Second test: the client leaves owing something. If only the firm has a task, nothing will have changed by the next call.
  • Red flag: three check-ins with the same blocker. The blocker is not a blocker, it is a priority, and that is a different and more honest conversation.

Rules

  • MUST name one milestone and hold it across check-ins until reached.
  • MUST distinguish delivered from in use, and report the second.
  • MUST read the shared working channel before the call, not just the record.
  • MUST send an agenda in advance.
  • MUST end with a dated commitment from both sides.
  • MUST raise a client-side blocker they have not acknowledged in the first ten minutes.
  • NEVER let a check-in become a status update. If there is nothing to move, shorten or cancel it.
  • NEVER count internal sign-off as activation.
3 reference files
references/activation-stages.md

Delivered is not in use

Two stages, tracked separately. Most firms track the first and report it as if it were the second.

StageWhat it meansWhat it looks like
BuiltThe work exists and the client has approved itSigned off, invoiced, sitting there
In useThe people it was built for are using itUsage, questions, complaints, requests

A client can sit at Built for months. Everything feels fine, invoices are paid, and at renewal they cannot name what it did for them, because nothing happened.

Mark the stage explicitly on every engagement and report the second one. The first is a milestone for the firm; the second is the only one that matters to the client.

Who "the people it was built for" are

Depends on the work, and naming them specifically is most of the job:

The workIn use means
A website or campaignLive, with traffic, and the client's team updating it
A brand or design systemOther people inside the client making things with it, without asking
A process or playbookTheir team following it without the firm in the room
Something client-facingTheir own clients using it, not just their internal team
A report or dashboardSomeone opening it in a meeting and making a decision from it

The last column is the milestone. Write it in those words.

Telling which stage a client is in

Three questions, answerable from the shared channel without asking the client:

  1. Has anyone outside the immediate project team touched it?
  2. Has anyone asked a question that only a real user would ask?
  3. Has anything been changed or requested since handover?

Three noes means Built, whatever the status field says. One yes means it is beginning. Three yeses means In use, and the engagement has done its job.

The gap between the stages

This is where engagements quietly die, and it is almost never the firm's delivery that causes it. Usual causes, in order:

  • No internal owner at the client. The sponsor bought it, nobody was assigned to run it.
  • It needs one more thing nobody scoped. A migration, an access grant, a piece of content, a decision.
  • The people it was built for were never told. Common and easy to fix.
  • Their priority changed. Honest, and worth knowing early.
  • Nobody is confident enough to use it. A training problem the firm can solve cheaply, if it hears about it.

Each has a different fix and only the last two need the client to do anything hard, which is why diagnosing before the call matters.

Measuring it

Per client, one line: current stage, the date it reached that stage, and how long it has been there.

Time at Built is the number to watch. Past a few weeks with no movement, the check-in stops being a check-in and becomes a conversation about whether this is still happening.

references/prep-card.md

The prep card and the agenda

Built in ten minutes before the call. Internal, except the agenda, which the client sees in advance.

The card

[CLIENT] - check-in [n] - [date]

MILESTONE: [one sentence, their words, unchanged since last time]
STAGE: Built, 5 weeks | In use

WHERE THEY ARE
[One sentence on what is actually true today.]

THE GAP
[One sentence: what stands between today and the milestone.]

BLOCKER: [what] | OWNED BY: [firm / client / third party]
[If client-owned and unacknowledged: RAISE IN FIRST 10 MINUTES]

SINCE LAST TIME
[What they said or did in the shared channel. Or: nothing, 3 weeks.]

LAST TIME'S COMMITMENTS
- Us: [what] - done / not
- Them: [what] - done / not

OPENER
[One question referencing something specific from since last time.]

Reading the shared channel

Before opening any record, read the working channel with the client. Five minutes, looking for:

  • Questions they asked, especially ones a real user would ask
  • Something they went quiet on after being enthusiastic
  • A new name appearing, which usually means a new stakeholder
  • Complaints, however mild
  • The last thing they said, and how long ago

Silence is the most informative signal here. A client who was active and has said nothing for three weeks has deprioritised, and the opener should be about that rather than about the milestone.

The agenda, sent in advance

Three lines, the day before.

Thursday's call, keeping it to 20 minutes:
1. Where we are on [milestone, their words]
2. [The blocker], and what we each need to do about it
3. What's next after this lands

Short, specific, and it names the blocker before the call so nobody is surprised into defensiveness.

Sent in advance it changes who prepares. A client who has read it arrives having thought about the blocker, which is the entire purpose.

The opener

References something specific since last time. "How's it going" gets "good, we've been slammed", which is a non-answer everybody has agreed to accept.

WeakStrong
"How's everything going?""You mentioned Priya's team would start using it after the quarter close. Did that happen?"
"Any updates?""I noticed the channel's been quiet for a few weeks. Has something else taken priority?"
"Are you happy with the work?""Has anyone outside your team touched it yet?"

The close

One commitment from each side, with a name and a date, said out loud and written into the record before the call ends.

The client-side commitment is the one that matters. An engagement where only the firm ever owes something is an engagement the client has stopped participating in, and that shows up at renewal as a surprise.

When to cancel instead

If the card has no gap and no blocker, there is nothing to move. Send two lines in the channel instead and give everyone the half hour back.

Cancelling a check-in that has no purpose builds more credibility than holding it, and it makes the ones that do happen matter.

references/stalled-engagements.md

When it stalls

An engagement sitting at Built with no movement for three or more check-ins. Common, rarely named, and the single largest source of quiet churn.

Recognising it

SignalWhat it means
Same blocker three check-ins runningNot a blocker, a priority
The sponsor stops joining, sends someone juniorAttention has moved
Calls get rescheduled twiceSame
Questions stopNobody is using it, so nobody has questions
"We've just been slammed" twiceHonest and final, unless something changes
Payment still prompt, engagement still deadThe most deceptive case. Money is not attention.

That last one catches people out. A client who pays on time and does nothing feels fine on a dashboard and will not renew.

The conversation

Have it directly, once, at the third stalled check-in. Not another agenda, a different call.

"We've had the same blocker for three calls now. That usually means something changed on your side, which is completely fine, but I'd rather know than keep booking these. Is this still a priority this quarter?"

Three things that makes possible. They say yes and commit properly. They say no and you stop burning time. Or they say what the real obstacle is, which is usually something they were embarrassed to raise.

All three outcomes are better than a fourth check-in.

If they say not now

Agree an explicit pause with a date to revisit, and stop the check-ins. A standing call nobody wants is worse for the relationship than an honest pause.

Record what would need to be true for it to restart. That sentence is what makes the restart conversation easy in two months.

If the obstacle is internal to them

Usually one of three: no owner assigned, a decision nobody will make, or someone quietly against it.

The firm can help with the first and sometimes the second. The third needs the sponsor, and the most useful thing to ask is who else needs to be comfortable with this.

Preventing the stall

Most stalls are set up at kickoff, not discovered later.

  • Name the internal owner at kickoff, not the sponsor. Different person, usually.
  • Define the milestone as a thing the client's own people do, not a thing the firm delivers.
  • Agree what happens after handover before the handover.
  • Put the first in-use date on the calendar at kickoff, with a name against it.

Those four take ten minutes at the start and prevent most of what this page is about.

Install this skill

Pick where your agent runs.

View prompt
Help me install the skill named "client-activation-checkin" from this GitHub URL in Claude:
https://github.com/agiea-brain/agency-skills/tree/main/skills/bailey-darling/client-activation-checkin

Prepare only the "client-activation-checkin" skill, not other skills in the repository.

Inspect each complete skill folder, not just SKILL.md. Preserve the original instructions and include all supporting files (such as references, scripts, templates and assets), keeping their relative paths intact. Package each skill as a downloadable ZIP containing its skill folder with SKILL.md directly inside that folder. If a skill only contains SKILL.md, package that folder too.

Give me the download link for each ZIP and walk me through uploading and enabling it under Settings, Capabilities, Skills in Claude. If you cannot access GitHub or create downloadable files here, explain what I need to download and how to package and upload it myself. Do not invent missing files or claim the skill is installed before I upload it.

Paste this prompt into Claude. It packages the skill folder, supporting files included, and walks you through uploading it under Settings, Capabilities, Skills.

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