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InfoQ Homepage Articles Building an Effective and Enjoyable Remote Onboarding Experience

Building an Effective and Enjoyable Remote Onboarding Experience

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Key Takeaways

  • Prepare for your next remote onboarding with a comprehensive checklist that provides the new hire with a curated and prioritised list of resources to consume and tasks to complete. This can include the key partners to meet with, historical context documents to read, and technical diagrams.
  • Establish quick wins the new hire can complete within the first few weeks that will help them build confidence and understand the full developer workflow.
  • Identify a technical mentor and peer buddy to enable the new hire to start building relationships and continue serving as approachable resources whenever they need assistance.
  • Build a curated list of resources the new hire can consume over the first few weeks that includes details about the who, what, when, where, how and why of your team and organisation.
  • (For managers!) schedule and prepare for weekly 1-1s to proactively identify blockers, discuss onboarding expectations, and (most importantly) start building trust.

The COVID-19 pandemic resulted in many new experiences and challenges for the software engineering industry. One in three employees transitioned to remote work in 2020 alone, and the Great Resignation resulted in many employees leaving their roles and onboarding to a new organisation.  

Teams across the world were left to scramble to quickly refine their processes to align with the nuances of virtual teams. Many of us were unsure if these investments would even be worth the effort - would it really be that long until we were able to return to our normal ways of working together in an office?  

Hindsight is 2020 (pun intended). Little did we know, building up those virtual muscles early on would absolutely be worth the investment.  

And so the world adapted. Teams introduced tools and technology to simulate the collaborative experiences of being together physically. We now have endless options of online agile project management tools, video conferencing, and more opportunities than we ever wanted to peer into our colleagues’ home living rooms. 

As amazing as this is, I believe we still have some work to do when it comes to mastering remote collaboration and team processes.

In this article, I’ll specifically be shining a spotlight on the onboarding process as I believe it is one of the most critical employee experiences to invest in.

Why is that?

The onboarding experience will make up the new hire’s first impression of your team and company, so it’s really the ideal place to set standards, and therefore requires thoughtful planning, patience, and compassion.  In this article, I will dive into some of my own learnings as I onboarded new team members remotely as well as my own wonderful experience joining a new organisation in 2021! 

The challenges of remote onboarding

Onboarding to a team remotely can feel very isolating. As you can imagine, it is much easier to facilitate natural interactions if a person is joining the team onsite - simply by introducing them to people they will be sitting next to and having them “tag along” to meetings.  

Therefore, it is important that teams are intentional as they plan a remote onboarding experience to ensure the new hire has several touchpoints before, during, and even after their first couple of months on your team.  

Touch points can vary from fun activities to get to know fellow colleagues to 1-1s with their manager and mentors to help answer questions to skip level meetings with upper level leadership to understand the context and direction of the organisation.  

Fun activities can include #watercooler channels for team members to chat about hobbies and passions outside of work such as #houseplants, #dogs, #TIL, #poetry, hosting a virtual game on a recurring basis, starting team meetings with an icebreaker question, or kicking each week off with a “photo of my weekend” thread! 

These touch points will help the person absorb as much relevant context as possible, start building trust and getting to know their team members, learn who or where to go for questions, and most importantly feel like they aren’t alone.  

On my first day joining a team remotely, my leader started a thread in our team Slack channel inviting peer colleagues to share a tidbit of advice for me as I was onboarding. This was very helpful (and welcoming!) experience that I really enjoyed.

As many of us know, it can also be challenging to maintain healthy work/life/balance while we are working from our homes. As a team, you can work together to establish and document boundaries and signals for team members to know each other’s availability. As an example, if you use Slack - you could use status messages and visual colour indicators such as: 

  • Available - green: I will be online, able to respond quickly; I’m focused on work
  • Connected - yellow: my response times will be longer because my focus might be in a meeting or addressing life needs
  • Unavailable - red: I am focused on life outside of work and will respond when I check back in

And for teams across different time zones - remind them that responses to off-hours emails are not expected immediately!

Lastly, new hires often feel anxious wondering if they are contributing enough - and if those contributions are visible to their colleagues.  Together as a team, proactively discuss what it means to be productive and meet expectations in their roles. Hint: quite often, this means focusing on results over time spent on something.

Preparing the onboarding experience

Many teams don’t spend enough time preparing for the onboarding experience. 

As soon as the offer letter is accepted, teams can take steps to continue validating the person’s decision to join your team to help them feel excited leading up to their first day.

As an example, you can send an email to the new hire ~two weeks before they join reminding them why you are excited for them to join your team (skills, background, stories that you discovered in the interview process) and an itinerary for the first week along with practical information that might be helpful.  This email could also include the login details for their new email, who they will meet with on their first day, and other onboarding experiences they can look forward to during week one.  

You can also use this touch point to request a quick bio from them so that you can properly introduce them on their first day - including a fun fact (favourite food, location they have travelled, or movie).  Bonus points for including a compilation of fun videos of their fellow team members welcoming them to the team!

Next, please(!) make sure you send them a laptop that is provisioned and ready to go for their first day.  Perhaps you can include some fun custom SWAG from your team and organisation. Getting as much of the administrative work out of the way before their first day will help ensure a productive and enjoyable experience for everyone.

A few weeks leading up to their first day, work with the team to build a comprehensive onboarding plan for the new hire. This can include instructions to get their local environment setup (step by step w/ screenshots), diagrams and visuals of your team’s architecture, dev tools, the team’s on call or support processes, preferred source control methods (branding/forking/etc), and the key partners they will be working with (peer developers, product owners, UX, etc).  Ideally this plan never becomes stale as the team keeps it updated just as they would any other technical documentation. 

It’s time to onboard! 

The first day has arrived - your new hire is able to log on and meet the team! Now, how can we help the person get up to speed with hands-on activities while they are consuming your wonderful onboarding plan?

I love the idea of finding quick wins that the person can complete to build confidence and start understanding the full developer workflow. An example would be saving smaller bugs or enhancements that aren’t on the critical path - tagging them with “onboarding task” so that the team knows to skip that task until the new person joins.

A couple of years back, I led a team who frequently hosted interns for 10 weeks in the Summer. Ten weeks fly by, so we wanted to make sure they could get up to speed as fast as possible, add value to the team, and not feel like they were working in isolation. We identified tasks for them to tackle while onboarding such as minor updates to form styling and consuming an upgraded version of an API. These tasks helped them quickly get familiar and understand different areas of the codebase.

More recently, another remote team saved larger (but relatively straightforward) engineering tasks for new hires to tackle such as working to convert a web app from using Semantic to Material UI component libraries. This initiative enabled the person to become familiar with all areas of the codebase plus a lot of business context as they had opportunities to ask questions about how the components were used along the way.

Perhaps you can even build an onboarding task that embodies a mini version of your app or models a real feature your team might create! 

The onboarding trio 

Remote onboarding can unfortunately feel isolating. As a team, we want to help the person build relationships immediately. Establishing an “onboarding trio” can help alleviate this concern by proactively identifying key players in helping the person feel connected right away.  

The trio includes a technical mentor, a peer buddy, and, of course, the new hire themselves.  

The technical mentor can assist the person in understanding the background context of the project and play a key role in helping them break down features and code reviews.  The mentor might be a bit more seasoned on the team - someone who has a lot of business domain expertise and is knowledgeable about the system processes and architecture.  

Now, let’s talk about the “peer buddy” role. This person makes themselves available to answer questions whenever the new hire needs something. Perhaps they were the person to join the team most recently so they are really familiar with what it feels like to be new and can proactively help that person have a great experience.  

It is important that the buddy can carve out a bit of time in the first month or two to ensure the new hire has a great experience because they are truly “accountable” for the onboarding experience of the new hire.  This means they should be accessible and available to answer questions throughout the day so that the new hire isn’t left waiting.  In a remote context, this could involve proactively setting up a video call at the start and/or end of each day together (week 1), a few times a week (weeks 2-4) and weekly check-ins after.  

In addition to the video calls, the buddy should share their communication preferences if the new hire needs something ad hoc (Slack, email, phone call?).  Lastly, the buddy should share clear expectations for when they are available to assist the new hire throughout the day - for example, it won’t be obvious if the buddy is in another meeting or offline and might be delayed in responding. If possible, sharing calendars can create transparency so that the buddy and new hire know when each other are available throughout the day.  

I recently joined an organisation and had an amazing experience largely due to my (two!) assigned buddies. Both individuals made themselves available any time I needed help - whether it was a question about an acronym I heard in a meeting, or a strategic initiative that we were working on. Knowing that I had specific people “assigned” to help with my onboarding experience made me feel well supported and set up for success!

Drinking from the firehose 

We want to make sure that we help the new hire get up to speed on the context of the project they are working on without overwhelming or distracting them with irrelevant information. Onboarding is going to feel like drinking from a fire hose no matter what, so let’s be thoughtful as we plan what to share and when!  

First, you can build a curated list of the resources they should read or watch to gain context of your team or organisation’s goals, mission, or culture, key partners to meet with, and when to complete each of these (ideally - week by week).  You can set up automated emails to share milestones and the reading list to remind them of helpful links - what is important for them to consume and learn and key partners to meet with at that specific time during their onboarding process. This will help to not overwhelm them in the first week!

Examples of key partners can include the team’s HR partner, leadership team, and direct team members. And for each of these individuals - what is their preferred communication tool? Ideally, the first meet would be via video call to start building the relationship. After that - if you need something from one another - do they prefer an asynchronous tool - like Slack, email - or do they prefer a video call?  The new hire can simply ask each person what their communication preferences are in the first introduction video call! 

Other examples in the curated onboarding list might include: 

  • What are the major pieces of infrastructure/services that the team owns and supports?  What are some of the upcoming initiatives that the team is going to tackle?  
  • What is the historical context for why this team exists?  
  • Acronyms?  
  • How does the team track progress?  
  • How does the team communicate and coordinate their work? 

Tips for managers

Similar to colocated team members, I believe the best managers take time and energy to ensure people on their teams have what they need to be successful and happy in their roles.

This means facilitating frequent (1x/week or bi-weekly) 1-1s.  A few examples of great questions to ask in the first few weeks include: 

(Week 1) 

  • What is your preferred way to receive feedback?  
  • How would you describe your communication style?  
  • What motivates you?
  • Do they need to be offline in the morning or afternoon to drop kids off?  
  • Do they have kids studying at home?  
  • Do they live in a location with unreliable internet?  

Starting to dig in and understand their existing environment will ensure you can help set them up for success right away - and make them feel like they don’t have to hide the realities of what is going on in their lives that might impact work.   

(Weeks 2-4)  

  • What are you most excited about working here?  
  • When have you felt frustrated, or overwhelmed?  
  • What still feels unclear to you?  
  • What has surprised you about our culture or your experience?

I would recommend every week asking a few pointed questions to get a signal if the person is feeling overwhelmed, or like they need more context or information about something. As an example, simply asking “What has been challenging this week?” or “Do we need to adjust your onboarding experience in any way - whether it be adding more resources/meetings to your calendar, or less to give you time to consume current resources?”  

It can also help to revisit expectations and be specific about what activities are most (and least) important for the person to focus on if they are feeling overwhelmed. As discussed, onboarding is going to feel overwhelming no matter what - but we can help manage that experience by effectively talking through those emotions and offering more support where needed. 

Even after the first few months, managers should continue taking a pulse on team members in the months following their onboarding experience. One option would be to send out a pulse survey asking team members to rate prompts on a scale of 1-10: 

  • I am confident using the tools/tech I need in my role
  • The onboarding experience gave me the opportunity to establish good relationships with people who are key to my success
  • I have quality 1-1s with my manager
  • I have a good idea about what is expected of me in my role
  • I have a good idea of what I can do to have a successful career here
  • I understand and can articulate the goals of my team and organisation 
  • My experience onboarding matched my expectations
  • I feel welcome here

Perhaps there are some high cost opportunities for managers to identify ways to support their new hires, which might include: can you pay for them to upgrade their internet?  Coworking space membership? Noise cancelling headphones? Standing desk/monitor?

We must put in the investment (time, money, and energy) to make sure our new hires have a great onboarding experience - before, during, and after day 1! 

Onboarding does not end after the first week, month, or even year. We need to continue supporting folks in their roles - sharing context, giving feedback, helping to set vision and direction, connecting them with opportunities to grow, and building intentional relationships.  We can even invite the new hire to help improve the onboarding experience for future colleagues by offering to be a peer buddy for the next new team member!

Wardin spoke about remote onboarding at QCon Plus November 2021

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