Onboarding someone properly

The first two weeks decide whether a good hire becomes a good employee. Most startups improvise this and lose months.

What is it?

Onboarding is the deliberate process of getting a new person productive and connected: access, context, a first meaningful task, and explicit expectations.

It runs for roughly the first month, not the first morning.

Why does a founder care?

Because a bad first two weeks costs months of output and is the single biggest predictor of an early departure. Someone who spends a week waiting for access and guessing at priorities forms a lasting impression of how the company works.

And because at a small company nobody else will do it. There is no HR function to catch what you forget.

Example

A bad first week: they arrive, spend two days chasing access, read whatever documentation exists, attend meetings without context, and are told to 'have a look around and see what needs doing'. By Friday they feel useless and are wondering whether they made a mistake.

A good first week:

Before day one: all accounts created, laptop ready, a written note explaining the company's current situation honestly — including what is going badly.

Day 1: meet everyone individually for fifteen minutes each. Walk through the product as a customer would use it.

Day 2–3: listen to three recorded customer calls. Read the last three months of investor updates. This gives more context than any handbook.

Day 4–5: ship one small real thing. Ideally something a customer notices.

Week 2: own a defined small project end to end.

Week 4: explicit conversation — how is this going, what is unclear, what surprised you? The surprises are valuable feedback about the company that you will never get again once they acclimatise.

The key move is shipping something real in week one. It converts anxiety into belonging faster than anything else.

The common mistake

First-time founders often assume a senior hire needs no onboarding. Seniority means they need less hand-holding on the work, not less context about the company. A senior person with no context makes confident decisions based on their last company.

The second mistake: not writing anything down, so every new person costs the same repeated explanation. Write it once at the second hire.

The third: skipping the four-week conversation. A new person sees your company clearly for about a month before they normalise to it. That perspective is genuinely valuable and it expires.

How it works

Step 1: Prepare everything before day one

Accounts, hardware, access. Chasing access on day one signals disorganisation immediately.

Step 2: Give honest context in writing

Where the company is, what is working, what is not. Including the bad parts builds trust fast.

Step 3: Have them experience the customer

Recorded calls, using the product, reading support tickets. Faster and better than any internal documentation.

Step 4: Ship something real in week one

Small, but genuinely used. It converts anxiety into belonging.

Step 5: State expectations explicitly

What success looks like at 30, 60 and 90 days. Written down, not implied.

Step 6: Have the four-week conversation

What surprised you? What is unclear? That fresh perspective expires and is worth capturing.

When to use this

Every hire, including senior ones and including contractors who will be with you for months.

When not to use it

Do not build a formal onboarding programme for your second employee. Write a one-page checklist, and let it grow as the team does.

Do this now

Apply this to your own startup in My Full Journey (free account).