2-Week Onboarding Bootcamp Plan

Section 1

Day 1 to 2: Orientation

The first two days are about making the new person feel welcome and giving them context. Cover who you are, what you do, how you work, and who the team is. Do not dump them into project work on day one.

Section 2

Day 3 to 5: Tools and Process Training

Teach them how you work. Walk through every tool, process, and workflow they will use. Do not just share login details and hope for the best. Sit with them (or screen-share) and show them how things actually work.

Section 3

Week 2, Day 1 to 3: First Project

Put them on a real project with training wheels. Assign a low-risk task with clear deliverables. Pair them with an experienced team member. The goal is not perfection, it is learning your process by doing.

Section 4

Week 2, Day 4 to 5: Feedback and Adjustment

The last two days are about reflection and calibration. Have an honest conversation about how the first two weeks went. What is working, what is confusing, and what needs to change. This is a two-way conversation.

Section 5

Onboarding Checklist

Use this checklist to make sure nothing falls through the cracks. Go through it before they start, during week one, and again at the end of week two.

Email account and calendar set up Do this before their first day so they can hit the ground running.

Slack/Teams access with all relevant channels Include project channels, not just general.

Project management tool access (Asana, Notion, Monday, etc.) Pre-assign them to a test or onboarding project.

File storage access (Google Drive, Dropbox, etc.) Give them access to templates and past project examples.

Design/dev tools and licenses set up Figma, Adobe, GitHub, etc. Do not wait until they need it.

Team handbook or operating doc shared If you do not have one, this is your sign to write one.

Org chart and reporting lines explained They should know exactly who they report to and who to ask for help.

Client list and active projects reviewed Give them context on who your clients are and what is in progress.

Company values and culture discussed Do not just share a document. Have a conversation about what they mean.

First project assigned with clear brief and deadline Make it real but low-stakes so they can learn without pressure.

Buddy or mentor assigned for the first 2 weeks Someone they can ask 'dumb questions' without feeling judged.

End-of-week-one check-in scheduled Catch problems early before they become habits.

End-of-week-two feedback session completed Two-way feedback. Ask how they are doing and how you can help.

30-day goals set and documented Clear, measurable goals so they know what success looks like.

2-Week Onboarding Bootcamp Plan

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