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We know that more and more people are starting new jobs remotely. But how does this affect the onboarding experience?

In times of uncertainty, we tend to become more risk-averse in our decision-making. Despite that, I took a leap of faith and accepted a new senior engineering leadership role at Shopify, just after they had gone to working fully remotely, permanently (what we call, ‘digital by design’). Six months into it, I am pleased to share that it has been an incredibly positive experience for me. I hope that you can leverage some of the factors that made the difference for me to benefit you and/or your team members. 

Acknowledging that ‘digital by design’ impacts people differently, I will also share my observations on the dangers that it can pose, and offer suggestions on how to steer around them for your own and your team members benefit.

Let’s dive into five key factors that made all the difference during my onboarding.

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Gathering context

At Shopify, we want to build a 100-year company. If you want to do that, one of the first things you need to do is record your history so that new hires can understand the stages that the company has been through and how the path of the organization has shaped its culture and values. You’ll usually learn this from talking to folks who’ve been around for a while. But it turns out that when you join a company remotely, you lose access to that rich historical context because you don’t have the opportunity to mingle with folks you are not directly working with. 

At Shopify, I have access to a vault of meeting recordings of all the ‘town halls’, key presentations, and AMAs over the history of the company. This treasure chest has been exceptionally critical for a new hire like me. It is a tremendous source of information to understand how we came to be and where we are going.

Your first 90 days

So, you’ve just started working in a new company. We know what that’s like. You have now lost all the credibility that you had built up with your old colleagues. Over the years, they had gotten to know you. They knew what you could do and how you added value. With a new set of colleagues, all of that is gone. In your new company, you are a brand new entity. You need to learn the new context, and understand the new domain and technology. You need to reestablish your relationships and, in a relatively short time, you need to prove yourself. In short, it’s stressful! 

My onboarding experience was a positive one because the organization acknowledges the challenges of joining a company remotely, and has structures in place to make it easier. Most importantly, the guideline to all new leaders is to refrain from the desire to jump in and make sweeping decisions until you have gained enough context. And there is the acknowledgment that it takes time. Your first 90 days just turned into your first 180 days! 

This approach was incredibly helpful for me. It allowed me to be more realistic with my own expectations of when I would be fully up-to-speed. When, ordinarily, 90 days is seen to be a rule-of-thumb timeframe, you can expect it to take more like 6 months before you have sufficient context to start making some of the higher impact decisions. 

If you are a hiring manager, take it into consideration to set the right expectations with your new hires and relieve one of the larger sources of stress that joining a new company can bring.

Asynchronous communication

One of the benefits of ‘digital by design’ is being able to tap into a wider talent pool across the globe. This is a win-win opportunity for employers and employees alike. Employers can increase the diversity within their workforce and employees get the opportunity to work for great companies that may have been out of their reach until now. 

While the benefits speak for themselves, it comes at a cost. How do you make a geographically-dispersed team productive? How do you make them feel like one team? Much has been written on this topic, but one cultural factor that has made a big impact at Shopify is a preference for asynchronous communication. 

Avoid getting into a meeting before the topic for discussion has been written down, and before the participants have had a chance to review and give feedback asynchronously. I have found that this approach has fundamentally changed the meaning and format of documents for me. Whereas documents used to be long and carefully crafted works of many hours of labour, they have turned into a tool to help us work through our thoughts and ideas. They give us structure and the space to reflect on our proposed ideas before we get into a ‘room’ and start talking. This fundamental shift to async has many advantages: it has cut down the number of meetings; it allows people in different timezones to gain visibility on the topics being discussed and the opportunity to engage; it has made the meetings we do have, more effective.

Written communication can’t replace synchronous communication entirely. When we do meet in a video conference, more likely than not, we will record it and share the recording with the rest of the team. When your team is 12 hours apart, video recording is a great way of leveling the playing field. 

Trust and transparency

During my onboarding, I was introduced to a concept at Shopify called the ‘trust battery’. The idea is that when you start working with a new group of people, they don’t know you so, in theory, they don’t know how much they can trust you. Over time as you make the right decisions and demonstrate your knowledge and your skills, you build up a trust battery with them. It turned out that at Shopify, people tend to start working with you assuming a full trust battery, which is a great starting point. While it’s true that it’s easy to lose that trust, if the starting point is a positive charge, you will ultimately become productive much faster. 


Any article written on working from home is not complete without mentioning self-care! For many of us, working in the office enforced a framework that helped us live healthier lives. We would wake up every day of the week, dress well, and get out of the house. We had socialization handed to us by the sheer number of people who work in the office. At least for some of us, when we left the office and drove or walked home, we mentally left work behind. All those structures have been lost. We need to proactively and, with intent, replace them with our own daily routines and structures. 

We have been living with the pandemic for a full year now. What structures have you put into place to ensure you have a healthy sustainable work-life balance?

Parting thoughts

As our COO put it, we have only just started this journey; a few years from now, our experience of WFH will be very different. We are learning the tips and tricks of making it work better for us. As a parting thought, I invite you to pick one thing you can do to make WFH more productive, enjoyable, and sustainable for you and your team, and commit to taking the first step towards it this week!

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Laying the foundations for remote success
Episode 02 Laying the foundations for remote success
Helping engineering teams adapt to a new normal
Episode 04 Helping engineering teams adapt to a new normal