Prepare for someone's first week.

Answer five short questions. You'll get a prep sheet to guide how you show up — so their first week actually sets them up.

Question 1 of 5

Who is joining, and what's their role?

Name, title, and start date if you have it (e.g. "Priya, Senior Engineer, starts Monday").

Question 2 of 5

How do you want them to feel by the end of week one?

Not what they need to learn — how they should feel. Safe, excited, clear, like they belong. Pick one or two words and then explain what that means in practice.

Question 3 of 5

What does someone need to know about how this team actually works?

The unwritten stuff. Communication norms, decision-making, what gets people stuck, who to go to for what. The things that take most people months to figure out on their own.

Question 4 of 5

What would make week one feel like a success — for them and for you?

Think small. One conversation, one deliverable, one moment. What would make you think "yes, that landed well"?

Question 5 of 5

What do you tend to drop the ball on when onboarding someone?

Be honest with yourself. Leaving them alone too long? Over-scheduling? Forgetting to check in? Naming it now means you can actually do something about it.

Prep Sheet

Onboarding —

The Goal

How you want them to feel by Friday

The Real Manual

What they need to know about how this team works

Suggested Welcome Message

Something to send before they start

What Success Looks Like

The small, concrete wins to aim for

Watch for This

Your known blind spot, named and ready

Before they arrive

Resources

From pre-start to 90 days — checklists, templates, and a guide for every kind of hire. Open what you need.

Per new hire

All hires

30 / 60 / 90 Day Plan

One plan per new hire — tracked in your Sessions. Set goals for each phase, note key people and check-ins, and share directly with the new hire.

Open →

Remote hires

Remote Onboarding Guide

Equipment, day one structure, async norms, connection plan, and early warning signs — everything that’s different when they’re not in the room.

Open →

A starting point — adapt to your team and context. The goal of day one is for them to feel held, not processed.

Morning

9:00
Welcome with manager
30 min. Coffee, tour, no agenda — just presence. They need to feel someone is genuinely glad they're here.
9:30
Setup time
Laptop, accounts, tools. Block enough time — this always takes longer than expected.
11:00
Team intro
30 min. Informal — no presentations. Names, faces, what people work on. Keep it light.
12:00
Lunch
With the manager or a small group. Not a working lunch.

Afternoon

13:30
How we work
30 min. Async norms, communication, decision-making, what gets people stuck. The unwritten manual.
14:30
Free time
Explore the tools, read the docs, settle in. No meetings. Protected space to breathe.
15:30
End-of-day check-in
15 min with manager. "Anything confusing? Anything missing?" Close with what tomorrow looks like.

Send the pre-start message a day or two before they begin. It costs two minutes and changes their whole first morning.

Pre-start (standard)

Hi [Name], Really glad you're joining us. Wanted to reach out before Monday so it doesn't feel like you're walking into the unknown. This first week is just about getting your bearings — there's nothing you need to produce or prove yet. We'll have time together early in the week and I'll make sure you know what the first 30 days look like. The team is looking forward to meeting you. And if anything comes up before you start, just message me. See you soon. [Your name]

Pre-start (remote hire)

Hi [Name], So glad you’re joining — and I know starting remotely can feel a bit strange at first, so I wanted to reach out before you begin. Your laptop should have arrived by now — let me know if anything is missing or not working. I’d rather know now than have you troubleshooting on day one. Your first day is designed to be light. We’ll have a call first thing, you’ll meet the team in the morning, and there’s space in the afternoon to just get oriented. Nothing to deliver, nothing to prove yet. If anything feels unclear before Monday, just message me directly. Looking forward to it. [Your name]

Internal move or promotion

Hi [Name], I know you already know us — but I still want to mark this properly. Starting a new role, even internally, is a real transition. The context you carry is an asset. The fact that you’re stepping into something new deserves its own beginning. This week, treat it as week one. There’s no expectation that you’re already up to speed in the new role — that’s what the next 30 days are for. We’ll have time together early in the week to talk through what the first month looks like. And if there’s anything you need from me to make the transition easier, just say so. [Your name]

Most onboarding problems are fixable if you catch them early. These are the signals to watch for in the first 60 days — and what to do when you see them.

Signal: Going quiet

Fewer questions, shorter replies, withdrawing from team channels

New hires often go quiet when they’re confused, overwhelmed, or worried about looking incompetent. It rarely means they’re disengaged — it usually means they don’t feel safe enough to say they’re struggling.

Repair: Book an informal check-in. Not "how is onboarding going?" but "I’ve noticed you’ve been quiet — how are you actually finding it? What’s been harder than you expected?"

Signal: Mismatch on expectations

The role isn’t what they thought it was

This happens when the job description and the reality diverge — different scope, different pace, different culture. If they seem disillusioned in weeks 2–4, this is likely the cause.

Repair: Have a direct conversation. "I want to check in on how the role is landing for you. Is there a gap between what you expected and what you’re seeing?" Acknowledge any real gaps honestly — then work out together what the path forward looks like.

Signal: Not connecting with the team

Feels like an outsider at week four

Culture fit takes longer than skills fit. If someone hasn’t found their footing socially by week four, it won’t happen on its own. The team needs to meet them halfway.

Repair: Brief the buddy or a peer. Ask them to take initiative — a coffee, an async chat, an invitation to something informal. Don’t wait for organic connection if it hasn’t happened.

Signal: Performance concerns emerging

The work isn’t where you expected it to be

If you’re seeing gaps in the first 30–60 days, the question to ask first is: did they have the context, clarity, and support to succeed? If yes, name it early. If no, fix the environment first.

Repair: Be specific and early. "I want to share some feedback before we get further into the role. Here’s what I’m seeing, here’s what I’d expect, and here’s how I want to support you in getting there." Early feedback is a gift. Letting it build until 90 days is not.

Sometimes a hire is wrong — for the role, for the team, or for the moment. Naming this early, clearly, and humanely is far better than letting it drift. This accordion is about how to have that conversation.

First: Are you sure?

Check your own reasoning before you act

Ask yourself: have they had a fair chance? Did they have the context, clarity, and support to succeed? Is this a skills gap, a cultural mismatch, or a management problem? Is the feedback you’ve given specific enough that they could actually act on it?

If you’re not sure, talk to HR before you talk to them. Not to protect yourself — to make sure you’re being fair.

How to open the conversation

Be direct, be specific, be human

Don’t circle around it. Say what’s true. "I want to have an honest conversation about how things are going. I’ve shared some feedback over the past weeks, and I don’t think we’re seeing the progress we need. I want to talk about what that means and what the options are."

Avoid: "things aren’t quite working out." That’s not specific enough. Be clear about what’s missing and what you’ve already tried.

The exit option

Name it without blame

If the decision has been made, say so clearly and treat them with dignity. "We’ve decided not to continue past the probation period. I want to explain why, and I want to make this transition as straightforward as possible for you." Give them the timeline, the practicalities, and the reference offer if applicable.

If there’s still a decision to be made, give them the honest picture: "Here is where things stand. Here is what would need to change. Here is the timeframe. I want to give you a real chance to make that case."