The Hiring Playbook · Part Two · The First 90 Days
Most owners spend six weeks finding the right person and six minutes onboarding them — then wonder why the hire underperforms. Onboarding isn't admin. It's the highest-leverage fortnight of work you'll do all year, and it happens before they walk in.
The Principle
You know the pattern. You interview hard, you pick well, you're genuinely excited — and then Monday arrives and you're on a job, so they get a login, a desk and a "sing out if you're stuck." Six weeks later you're quietly wondering whether you got the hire wrong.
You almost certainly didn't. The constraint is rarely the person — it's the system they landed in. Put an A-player into a vague first month and you get B-player results, because nobody ever told them what winning looked like. You can't hold someone to a standard you never communicated.
This page turns what's in your head into three documents: the plan you hand them on Day 1, the run sheet that gets you ready before they arrive, and the three review agendas that stop it drifting. Half an hour here saves you three months of hoping.
A ramp plan is not a to-do list. It is a documented transfer of ownership — from you to them — across every area of the role.
Which means the question at Day 90 is not "did they learn?" It's "do they own it?" If the answer is no, that's a plan you never wrote, not a person you shouldn't have hired.
The Shape
Ninety days, three phases, thirty days each. Every phase has one job, a set of deliverables, and an honest conversation at the end of it. The mistake almost everyone makes is expecting Phase 3 behaviour in Phase 1 — measuring output in the first month, when the only thing worth measuring is understanding.
The goal is context, not performance. Who's who, which clients matter and why, how work actually flows, what good looks like here. Resist the urge to measure output. Measure understanding.
Expectations arrive. They know enough to be held accountable, so the training wheels come off. Core responsibilities run independently, KPIs get tracked, real output lands.
The question isn't whether they can do the job — you know that by now. It's whether it runs without you. You should be able to leave their area for a week and come back to it better.
Most performance problems are visible by week two if you know what you're looking at. The point of a checkpoint isn't paperwork — it's forcing yourself to name what you're already feeling, at a point where it's still fixable.
One question at every checkpoint, and answer it honestly: would this person run this function without me needing to be there? If it's not heading towards a clear yes by Day 60, say so at Day 60 — not at month six when you've quietly given up.
The Method
Most managers do one of two things: dump the task and disappear, or hover and never let go. Both create the same result — a person who can't be trusted with it, and an owner who's still doing it. This is the third option, and it works on anything you need to hand over.
Skipping Show because you're busy. It's the fastest stage and the one that decides everything — twenty minutes of narrating your thinking saves you three weeks of correcting theirs. If you haven't got twenty minutes to show them properly, you haven't got the three weeks either.
Before They Arrive
If the contract lands late, nobody's told them where to park, and their login isn't set up — you've already communicated your standard, and it isn't the one you talked about in the interview. This is your first brand impression as an employer, and it happens before they've done a minute's work.
Tick what's already done. Whatever's left comes out on your run sheet at the bottom of the page, with dates against it.
0 of 12 done — the rest go on your run sheet
They will learn almost nothing useful on their first day, and that's fine — Day 1 isn't about information. It's about how it makes them feel. First impressions of a workplace are emotionally sticky, and you get one. Make it feel like joining a team that has its act together.
The owner personally welcomes every new hire — even for ten minutes, even on the busiest day of the year. It signals that this person matters and that the culture is real rather than HR theatre. For a senior hire it isn't optional.
The Builder
The biggest onboarding failure isn't a bad hire — it's an undocumented role. If you can't write down what great looks like, you can't train to it, measure it, or hold anyone to it. Rough notes are fine. Nothing here leaves your browser, and everything saves as you type.
Put the start date in and the whole plan dates itself — Day 30, 60 and 90, the first deliverable, and the deadline for their contract.
Add a date and every milestone below gets a real day against it.
If someone is leaving, or has already left, that window is the single biggest risk in the whole plan. Leave it blank if the role is brand new.
This is the part everybody skips and the part that does the work. You're carrying all of this in your head already — it just has to come out before they arrive, not after.
One measure, in plain words. If you can't name it, they can't hit it.
Writing these down is the cheapest thing on this page. You've watched them happen before — now they can be warned.
Every area of knowledge, skill or responsibility that has to transfer. Be exhaustive — this becomes the backbone of the training plan and the thing you audit at Day 90.
Format is up to you. "Thing — who owns it now — transferred by when" reads best in the finished plan.
This goes on page one of the document you hand them on their first morning. Write it like you'd say it, not like a contract.
The "why you specifically" line is the one people remember. Be concrete: it was the way you talked about your last team, not "your experience".
Context, not output. What do they need to understand before they can be useful, and what one real thing can they produce in their first fortnight?
Give them something that genuinely helps you. Nothing builds belonging faster than contributing in week two.
From Day 31 the expectations arrive. This is also where you kill the bottleneck — being clear about what they decide without you is worth more than any training.
Specific and measurable. "Better communication" is not a KPI — "I hear about a problem before the client does" is.
This is the freedom benchmark — the actual reason you're hiring. Write it as if you're going away for a fortnight on Day 91.
Culture isn't absorbed, it's installed. Pick the standards you'll actually enforce — then walk through them out loud on Day 1 and revisit them at every check-in. What you let slide in month one becomes the standard forever.
0 picked
A weekly one-to-one isn't a status meeting — it's an early warning system. Half an hour a week surfaces things three months before they'd otherwise reach you. Tick what you're genuinely committing to; the reviews aren't optional.
Checklists aren't for people who don't know what they're doing. They're for people who do, and want to do it consistently — a pilot with ten thousand hours still runs a pre-flight. For the first 90 days, the checklist is the job.
Your Plan
Read the gameplan out loud once. Anything that doesn't sound like you, change — that's the whole job. Then print it, hand it over at one o'clock on Day 1, and walk them through it line by line.
If the welcome reads a bit stiff or the plan feels generic for your trade, this prompt gives an AI everything it needs to rewrite it in your voice — without letting it wander off and invent responsibilities you never mentioned.
Put Day 30, 60 and 90 in both calendars now, while the plan is open. A review that isn't booked is a review that doesn't happen — and the whole value of this is having the honest conversation while it's still early enough to fix.
Then read the last line of the gameplan back to yourself. If you're not willing to be held to your half of it, take it out before they read it.