Guide to Remote Onboarding

Overview
This post is intended to provide a guide to onboarding in our remote situation. Ultimately, the majority of remotely onboarding just the same as in person onboarding, so great books like First 90 Days are still incredible resources, but right now onboarding must also be much more intentional as there isn’t a flow of traffic to hop into that will carry you up to speed even if you do nothing. If you do nothing these days, you’ll sit at home alone and do nothing. And you likely didn’t join this team to do nothing. 

To onboard, you need to understand what the team is doing (projects), how those get done (the team), and how you contribute to that (your role). In the process, you are also building your key relationships. So, at a high level, that’s what it means to onboard. 

The Onboarding Process
How you actually accomplish this task can be done in a few different ways, which likely depends on your role. You can focus on 

• Specific Projects: Create a deliverable and drive towards that learning what you need just in time. You’ll do it wrong, but the first step to doing anything right is usually doing it wrong - which is much better than doing nothing.  This gets you to being useful quickly in one domain, then you can expand to further domains after that.
• Person-by-Person: Meet with each person and understand what they do in depth. You’ll hear what’s important to various teammates, and thus the team as a whole. You can gather historical context. You can build relationships quickly.
• Domain-Oriented: Dive into the various teams around yours to learn what eng is doing, how BD is prioritizing their efforts, what complexity is most pivotal to the product managers, etc. This is very dependent on your exact team and positioning. Keep in mind that you have natural strengths you may gravitate towards, so build confidence where you have the most competence, but don’t neglect the places you will need to invest more into! Consider making a plan for how to approach each domain (see example below).

For me as a PM, it’s made the most sense to spend some time in each approach. 

Communication
The first step for communication is setting expectations and requesting support. This is incredibly important so others around you know how to help. If you don’t tell people what you need, they’re especially unlikely to see it by happenstance these days. So step 1, know yourself well. Step 2, tell your manager and teammates what you are confused by, what you’re strong and weak in, and what you will and won’t be able to do by when. Your team wants you to succeed as much as you want to succeed, so be clear with what you need and the whole team will benefit. 

Another key component of ingraining yourself in the team is constant communication. So keeping a direct line of contact for your teammates to understand your needs and current domain understanding is important. This can be done through

• Daily standing 1:1s used for ramping up, asking your inevitable deluge of questions
• Daily update emails you send to your manager or teammates with whatever is on your mind, in your way, in your focus, how you’re feeling, etc - note, this is *great* way to find answers to questions when you don’t know who to ask
• Open questions doc you share with your manager they can hop into any time and answer your questions

The Mental Aspect
While I’m tired of hearing the phrase “These are uncertain times”, we are in a….a phase of uncertainty. This can be a constant stressor on anyone as we don’t know what anything will look like in a month, not to mention the added stress of family commitments, health, economic challenges etc. This is all to day, everyone is more stressed than usual, even latently in ways they may not notice. So give yourself a break. There aren’t playbooks for this, so we’re all figuring this out as we go along. Give yourself a break when you’re getting yourself worked up. Remember your best is good enough. So it’s just about diligence and consistent effort from there.

Quick Tips

• Send a daily email to your manager with anything from what your focused on, things your thinking about, things you’re blocked on, how you’re feeling, plans you have going forward.
• Ask for help clearly and early.
• Share things early and get feedback early, just be sure to set expectations around what you’re sharing so they know what level of feedback to give you. 
• Schedule a daily 15 min 1:1 with your mentor. Ask them your questions as you go in this time. 
• Make an explicit plan for yourself, share with manager
• Have one doc of all your running questions. Share with your manager, let them answer Qs whenever they want
• Communication is extra important - be very explicit when you want someone to do something, repeat back to others what your heard if they’re asking you to do something
• Ask for a day to day manager if you’re not getting enough support
• How to know when to go deeper into a subject or not
  • Think about if the details are related to your role or not. If the details are purely details owned by another function, maybe pull back, they aren’t something you’ll need to account for going forward. If the technical details are related to your function, then keep asking questions until you deeply understand.
• For each of your nearby team leads (TLs, TLMs, Product leads, etc) 
  • Outline mission, concrete goals/milestones/etc, their definition of success
• Give yourself an emotional break. Keep working hard, but know that this is a challenging process.

Structured Understanding of your Team, Projects, & Role
The following matrices are valuable to fill out to solidify your understanding of the team. This is always true, but for some reason, the team and project structures are that much more ambiguous when you are remote. 

​Building alignment on the content of these tables is your first major contribution. After articulating the problem you're well set up to define the solution.

Team Definition

Project Definition
​A list of all projects going on that you are related to. Lower fidelity info is needed for projects which are less relevant to you.

Role Definition

Other Resources

• Gitlab’s Guide to All Remote Working

Example Domain-Oriented Onboarding Template

• Product (1 day)
  • What are we doing generally and why?
  • What projects are ongoing now? What timelines are we working towards on those
  • What have we tried before? What failed and why? 
• Technical (3-5 days)
  • How does everything work? What are the challenges?
• Relationships/Business (2 days)
  • What are the external+internal relationships we have? How are those going? Where can we expand those? Who is pushing us versus us pushing to them?
  • What are the relationships we still need?
• Operations (1 days)
  • What are the processes we run? (Incl. comms, reviews, launch, team org)
  • How can I effectively take over the ones I need to take over?
  • What parts of our process are difficult/could be improved? 
  • What mistakes have we made in launches or reviews?
• Data (1 days)
  • What do we have tracked?
  • Explore the dashboards, ask all the questions you have
• Financials (2 days)
  • What things cost a lot? Where are we wasteful? 
  • What have we done in the past that had high/low impact?
  • What’s the perception of our financials by surrounding teams?
• Review: Taking Action
  • What are the first things I can do to make a contribution to the relevant domains?