I had been in the same engineering org for seven years before the pandemic hit. We were a highly collaborative and co-located company and the team were very used to brainstorming and working on physical whiteboards and workspaces. When it did, we moved pretty seamlessly from working together from our office to working from our homes. We didn’t pay too much attention to designing a Digital First culture and neither did we alter our ways of working dramatically. 

It was only when I joined Shopify last September that I began to realize that working remotely in a company where you have already established trust is very different from starting in a fully remote space and building trust from the ground up. 

What Is Different About Starting Remotely?

So, what changes? The one word that comes to mind is intentionality. I would define intentionality as “the act of thoughtfully designing interactions or processes.” A lot of things that happen seamlessly and organically in a real-life setting takes more intentionality in a remote setting. If you deconstruct the process of building trust, you’ll find that in a physical setting trust is built in active ways (words you speak, your actions, and your expertise), but also in passive ways (your body language, demeanor, and casual water cooler talk). In a remote setting, it’s much more difficult to observe, but also build casual, non-transactional relationships with people unless you’re intentional about it. 

Also, since you’re represented a lot more through your active voice, it’s important to work on setting up a new way of working and gaining mastery over the set of tools and skills that will help build trust and create success in your new environment.

The 90-Day Plan

The 90-Day Plan is named after the famous book The First 90 Days written by Michael D. Watkins. Essentially, it breaks down your onboarding journey into three steps:

1. First 30 days: focus on your environment
2. First 60 days: focus on your team
3. 90 days and beyond: focus on yourself.

First 30 Days: Focus on Your Environment

Take the time out to think about what kind of workplace you want to create and also to reach out and understand the tone of the wider organization that you are part of.

Study the Building 

When you start a new job in a physical location, it’s common to study the office and understand the layout of, not only the building, but also  the company itself. When beginning work remotely, I suggest you start with a metaphorical study of the building. Try and understand the wider context of the organization and the people in it. You can do this with a mix of pairing sessions, one-on-ones, and peer group sessions. These processes help you in gaining technical and organizational context and also build relationships with peers. 

Set Up the Right Tools

In an office, many details of workplace setup are abstracted away from you. In a fully digital environment, you need to pay attention to set your workplace up for success. There are plenty of materials available on how to set up your home office (like on lifehack.org and nextplane.net). Ensure that you take the time to set up your remote tools to your taste. 

Build Relationships 

If you’re remote, it’s easy to be transactional with people outside of your immediate organization. However, it’s much more fun and rewarding to take the time to build relationships with people from different backgrounds across the company. It gives you a wider context of what the company is doing and the different challenges and opportunities.

First 60 Days: Focus on Your Team

Use asynchronous communication for productivity and synchronous for connection.

Establish Connection and Trust

When you start leading a remote team, the first thing to do is establish connection and trust. You do this by spending a lot of your time in the initial days meeting your team members and understanding their aspirations and expectations. You should also, if possible, attempt to meet the team once in real life within a few months of starting. 

Meet in Real Life

Meeting in real life will help you form deep human relationships and understand them beyond the limited scope of workplace transactions. Once you’ve done this, ensure that you create a mix of synchronous and asynchronous processes within your time. Examples of asynchronous processes are automated dailies, code reviews, receiving feedback, and collaboration on technical design documents. We use synchronous meetings for team retros, coffee sessions, demos, and planning sessions. We try to maximize async productivity and being intentional about the times that you do come together as a team.

Establishing Psychological Safety

The important thing about leading a team remotely is to firmly establish a strong culture of psychological safety. Psychological safety in the workplace is important, not only for teams to feel engaged, but also for members to thrive. While it might be trickier to establish psychological safety remotely, it’s definitely possible. Some of the ways to do it:

1. Default to open communication wherever possible.
2. Engage people to speak about issues openly during retros and all-hands meetings.
3. Be transparent about things that have not worked well for you. Setting this example will help people open themselves up to be vulnerable with their teams.

First 90 Days - Focus on Yourself

How do you manage and moderate your own emotions as you find your way in a new organization with this new way of working?

FOMO Is Real

Starting in a new place is nerve wracking. Starting while fully remote can be a lonely exercise. Working in a global company like Shopify means that you need to get used to the fact that work is always happening in some part of the globe. It’s easy to get overwhelmed and be always on. While FOMO can be very real, be aware of all the new information that you’re ingesting and take the time to reflect upon it.

Design Your Workday

Remote work means you’re not chained to your nine-to-five routine anymore. Reflect on the possibilities this offers you and think about how you want to design your workday. Maybe you want meeting free times to walk the dog, hit the gym, or take a power nap. Ensure you think about how to structure the day in a way that suits your life and plan your agenda accordingly.

Try New Things

It’s pretty intense in the first few months as you try ways to establish trust and build a strong team together. Not everything you try will take and not everything will work. The important thing is to be clear with what you’re setting out to achieve, collect feedback on what works and doesn’t, learn from the experience, and move forward.

Being able to work in a remote work environment is both rewarding and fun. It’s definitely a new superpower that, if used well, leads to rich and absorbing experiences. The first 90 days are just the beginning of this journey. Sit back, tighten your seatbelt and get ready for a joyride of learning and growth.

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