30-60-90 — Set Up Your Engineering Hires for Success

Week 1

Assign a buddy or mentor but avoid using a direct manager for this, as the person won't be that open and comfortable with their manager.
Less emphasis on paperwork, focus more on mission, impact, values and culture.
Set up an interactive onboarding task to keep them engaged from day 1.
Encourage them to ask questions, voice concerns, and share ideas openly. It's very important to teach them to not remain limited to DMs and become comfortable in public channels with the whole team.
Help them set up 1:1s with different members of the team

Make sure their local set up is up and running.
Assign small tasks to them. This can be small bugfixes, features and any documentation update. Documentation update is a must, especially the docs they are going through during onboarding.

Always have tasks in your backlog that are tagged as good-first-task.

Very important for them to have something live on prod as soon as possible, as that builds up confidence. That means the initial tasks should not involve a lot of back and forth. The goal is to move fast and deploy on prod and get a quick understanding of the system.
Ask the senior folks with whom they will be directly working to set up regular pair-programming sessions with them. Very important in early days to ensure they feel comfortable and have someone who actually shows them how things are being done.
Encourage them to dogfood the product. We want their own fresh perspective the way a new user interacts with the product.
Set up weekly 1:1 with them as manager.
Have them identify gaps in documentation or processes for a fresh perspective.

Set up slightly bigger tasks for them. Something that would require critical thinking and creativity from their end. Do not spoon feed the task, instead let them go through it themselves and come back to you with their own understanding.

The goal is to help build confidence and see if they are able to fill in the gaps for the things that are not mentioned explicitly.

Keep an eye on whether they are asking for help or struggling silently.
Check if they are actively participating in Slack discussions and in meetings.
Ensure they are learning from mistakes and are avoiding them in the future. It's also important to see if they pass on the same knowledge to others in the team.

By the end of this month they should be actively contributing to technical or non-technical discussions.
Delivering at least one meaningful project really helps overcome imposter syndrome.
They should be able to work on their own to an extent.
They should have strong opinions on things. They should challenge, ask questions, and propose solutions. If they are too passive, they are likely not a good fit.
If they are repeating the same mistakes, either coding or process related, then try to understand what's causing it.
Check if they appear busy but are not taking any ownership. Do they help others but aren't finishing their own work? These are some clear signs of procrastination.
Keep an eye on their code reviews. Are they mostly just accepting everything and not really providing much feedback? How are they interacting in code reviews?