The First 90 Days OS: Your Boot Sequence (and why Day 1 is already late)

You don’t get judged for what you know in Week 1.

You get judged for your defaults.

• Do you communicate clearly?
• Do you follow through?
• Do you ask good questions without creating extra work?
• Do you seem like someone your manager can trust with the next thing?

That’s the Boot Sequence.

Scene

Week 1 is a blur:

• new systems
• new acronyms
• new people
• and a lot of “where do we keep the latest version of ___?”

If you don’t install a few basic defaults early, you end up living in a loop:

1. you’re confused
2. you ask a question
3. you get an answer
4. you forget it
5. you ask again

That doesn’t make you dumb.

It just means you don’t have a system yet.

The Boot Sequence is how you get one.

Promise

This is the Week 1 setup that makes you look calm and competent fast:

• 3 questions to define “good” in plain English
• a note system that prevents repeat confusion
• a weekly update that buys trust
• one small win that proves you close loops

What prompted this

I keep seeing the same hot loop from new grads: start job → work hard → get vague feedback like “be more proactive” → panic. The comments are always split between “just hustle” and “your manager should train you,” but the truth is boring: you need a simple operating system. A few threads that capture the vibe are https://www.askamanager.org/2012/08/how-to-start-your-new-job-properly.html and https://www.askamanager.org/2019/01/i-dont-have-any-work-to-do-at-my-new-job.html.

The Boot Sequence (Week 1)

1) Get a real definition of “good” (in plain English)

Most new hires guess what matters. Then they optimize for the wrong thing. Then they get hit with: “Why did you do that?”

Your goal in Week 1 is to get answers to three questions:

1. What does success look like by Day 30?
2. What should I NOT work on yet?
3. How do you want updates? (Slack vs email, cadence, format)

Script (use this in your first 1:1):

“To make sure I’m aiming at the right target — what would you want to be able to say about me 30 days from now? And are there any traps you’ve seen new hires fall into that I should avoid?”

2) Install your note system (so you stop asking the same question twice)

If you remember nothing else: your memory is not a system.

Make one doc called:

“My Job: Notes + Decisions + Glossary”

Then keep these sections:

• People + what they own (names, responsibilities, preferences)
• Decisions (what we decided + why)
• Recurring rules (“we always do X before Y”)
• Glossary (internal acronyms; yes, it matters)
• My open questions (so you batch them)

This is how you look sharp without “trying hard.” You just… stop repeating yourself.

3) Make your manager’s life easier (quickest way to earn trust)

Managers don’t need you to be brilliant in Week 1.

They need you to be low-friction.

Do this:

• Send a short end-of-week note (Friday afternoon):
  • what you learned
  • what you shipped (even if small)
  • what’s blocked
  • what you’re doing next

Template:

Week 1 quick update

Wins: …

In progress: …

Blocked on: … (here’s what I tried)

Next up: …

One question: …

That last line is important. One question. Not twelve.

4) Ship one small thing (so you’re not “the new person who’s still ramping”)

Pick something that is:

• low risk
• small
• visible
• actually useful

Examples:

• Update a doc that everyone complains is outdated
• Fix a tiny bug
• Summarize a meeting into clear next steps
• Write a “how to run this process” checklist

The point isn’t impact. The point is signal:

“I close loops.”

5) Build a tiny relationship map (so you don’t get blindsided)

Your org chart is not the power chart.

In Week 1, identify:

• 1 person who reviews your work
• 1 person who unblocks you
• 1 person who gets mad if you surprise them

Then ask your manager:

“Who should I be aligned with early so I don’t accidentally create extra work for someone?”

Two quick notes, depending on where you sit:

• Early-career: don’t aim to look “smart.” Aim to look reliable. Reliability compounds.
• Manager: you can cut Week 1 anxiety in half by explicitly answering: “What does good look like?” and “How do you want updates?” New hires will fill silence with guesswork.

Edge cases

• If your role is highly technical and you can’t ship anything Week 1, ship a ramping artifact (glossary, environment setup doc, “how I built this” notes).
• If your manager has no time for a real 1:1 yet, send the 3 questions in writing and ask for quick answers asynchronously.

Next step

Schedule 15 minutes today to set up your “Notes + Decisions + Glossary” doc. Then paste the Friday update template into a draft message so it’s ready when the week ends.

If you want the full copy/paste checklist version, go to Week 1 Checklist.