Running onboarding in Slack

I've already written two skills for onboarding: one that documents how onboarding runs at your company, and one that builds the plan for each new hire.

But a plan is only as good as the people following it. You probably already have plans set up. The problem starts in week two.

Managers forget to book the 1:1s. New hires forget there's a checklist. Nobody updates the tracker, because nobody opens it. So you spend your week in DMs: "Did the intro meetings happen?" "Laptop out yet?" Then you update the plan yourself, and do it again next week for every hire you have running.

The fix is to stop asking people to visit another tool. Put the plan where they already work, in Slack, and let AI do the checking.

Here are the two places where AI helps:

→ The plan in Slack. Create each hire's plan as a Slack canvas with checkboxes, and draft the messages that share it with the new hire and their manager.

→ The tracking. A weekly check that reads every plan, tells you what's late and whose it is, and drafts the reminders for you to send.

1. The plan as a Slack canvas

A plan in a tracker is a plan for HR. A plan in Slack is a plan for everyone.

A manager who never opens Asana will tick a box in a canvas linked in their DMs. Owners show up as Slack mentions, so nobody wonders whose a task is. And when a new hire is stuck, they comment on the item right there instead of staying quiet.

Open your assistant and paste this, with the hire's details filled in:

Effy, build an onboarding plan for [role] in [department], manager [initials], starting [date], based in [country]. Stop at the review pack and wait for my go.

After I approve:

1. Create a Slack canvas titled "Onboarding: [role], [start date]":
  - at the top: start date, manager, buddy and HR contact, as Slack mentions
  - a two-line note: tick a box when it's done, comment on the item if you're blocked
  - one checklist per phase: Before day 1, Week 1, Days 2–30, Days 31–60, Days 61–90
  - every item: the task, one owner as a Slack mention, the due date
  - the 30/60/90 goals, marked DRAFT, owned by the manager

2. Add one line to the canvas "Onboarding: active hires" (create it if it doesn't exist): role, start date, manager, link to the new canvas.

3. Draft two Slack messages in my voice. Send nothing.
  - To the manager: the canvas link, what's theirs in the first two weeks, and one ask: tick items as they get done.
  - To the new hire, only if their Slack account exists: a short welcome, the canvas link, what's theirs in week 1, and who to ask about what. If the account doesn't exist yet, remind me to send it on day 1.

4. Tell me what you created, with links, and anything you couldn't do.

If you haven't connected Effy, open the onboarding-plan prompt, paste it into your assistant first, then paste the steps above.

How it works. It builds the plan from your onboarding process document: every task with one owner and a real due date. Then it stops. Nothing goes into Slack until you've read the plan and said go.

After you approve, it turns the plan into a canvas, one checklist per phase. It adds the hire to an index canvas, "Onboarding: active hires", which is how the weekly check finds every plan later. It's also your one-glance answer to "how many onboardings are running right now?"

The two messages land in your Slack drafts. You read them, change what doesn't sound like you, and send. When you do, make sure the manager and the new hire can edit the canvas, not only view it. A checklist nobody can tick is a poster.

2. Tracking progress, every week

The plan is at its best on day one. By week three, the 1:1 has quietly stopped recurring and a question from the new hire has gone unanswered for four days.

So set up a check that runs every Monday without you. Open Claude Cowork, start a new task, and paste this:

Create a scheduled task called "Slack onboarding check" that runs every Monday at 8:30. Each run should:

1. Open the Slack canvas "Onboarding: active hires". For every hire who started in the last 90 days or starts in the next 30, open their onboarding canvas.

2. For each canvas, compare the checklist against today's date:
  - overdue: unticked items past their due date. What, whose, how many days late.
  - due this week: unticked items due in the next 7 days.
  - not ready: anyone starting within 14 days with "Before day 1" items still open.
  - blocked: comments on the canvas nobody has answered.

3. Write me one report. Start with one line per hire: on track, slipping, or stuck. Then overdue items grouped by owner across all hires, worst first. Initials only.

4. Draft one reminder per owner, not per task, as a Slack message from me: what's open, the due dates, the canvas link, and "tick it when it's done." Short, in my voice. Send nothing.

5. Don't edit any canvas. If a hire is past day 90 with everything ticked, suggest I move them off the active list.

Before you create it, show me the task so I can check it. Then run it once now, so I can see the first report.

Claude sets up the scheduled task for you. You'll find it in your list of scheduled tasks, where you can change the day or time, pause it, or run it by hand. From then on, it runs every Monday on its own, and the report and drafts are waiting when you start your week.

How it works. Every Monday it reads the index, opens each active hire's canvas, and compares what's ticked against the dates. You get one short report: who's on track, who's slipping, and the late items grouped by person.

Two details matter more than they look. It drafts one reminder per person, not per task, so a manager with three late items gets one message, not three. And it reads the comments on each canvas, because a comment is usually a new hire saying "I'm stuck" in the politest way they know.

Drafts, never sends. The check could send the reminders itself. It shouldn't. People answer HR. They learn to ignore a bot within two weeks, and then they ignore the canvas it points to. Reading three drafts and pressing send takes a minute.

It only sees what's ticked. If a manager booked the meetings but didn't tick the box, the item shows as late, and your reminder says "tick it when it's done." Within two or three weeks, people tick as they go, because unticked boxes put their name in a Monday message. On the first run, ask your assistant to read one canvas back after someone ticks a box, to confirm it sees the tick.