Keyfer Mathewson

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Over the past few years at Shopify, I’ve had the pleasure of onboarding dozens of developers. The onboarding process is a living beast, that continually evolves, but I’ve begun to identify what makes a meaningful and welcoming first experience.

Initially, I believed a proper onboarding was simply making sure the new hire has everything they need: laptop, desk, software. The more I went through this process, the faster I got at setting up devs with the tools they needed. It’s incredibly fun to start at a new company and use new technology, but I’ve come to realize hardware and software shouldn’t be the focus.

Onboarding should focus on long-term impact, rather than short-term contributions. To set someone up for the long-term, these are the key areas to focus on:

  1. A sense of belonging
  2. Storytelling
  3. Understanding the work
  4. Empathizing with the customer

A sense of belonging

A sense of belonging is crucial during an employee’s first few days and weeks at a company. It is important that employees have support not only from peers but also from their lead; more important still is a feeling that they are in the right place. It’s the difference between passive help and active inclusion.

One approach I’ve taken to aid in this is to encourage existing members of the team reach out to new hires and book an informal fifteen-minute coffee chat. I’ve seen these first-week conversations turn into long-term friendships. The goal of this is so that whenever the new hire has any questions, they have an entire team that can help them.

I also encourage existing team members to take an active approach to this relationship. “Let me know if you want to get coffee,” turns into, “Hey, let’s go grab a coffee.” It’s a minor adjustment, but it’s crucial to make the new person feel welcome, and that they’re a wanted part of the team.


Storytelling can come in many different ways at work, but the two I’ve found most valuable are sharing personal experiences and sharing the history of the team.

Sharing personal experiences is an especially effective way to help a new hire combat imposter syndrome. Most of us have been there, and can empathize with feeling insecure.

Share your story. Share your experiences during the first few weeks, share what helped you push forward, and share your failures. These nuggets of information can be invaluable for someone trying to find their way at a new workplace.

Sharing team history is another essential piece of the onboarding puzzle. Every existing team has gone through iterations, and new teams are born for a reason. This is different than explaining the work - this is sharing the why behind the team. Having historical context on the problem area you’re working on, what’s worked and not worked in the past, is essential knowledge.

Understanding the work

By understanding the work, I don’t mean understanding what a designer needs to design, or a developer needs to build.

What I’m referring to is the deep-seated understanding of the problem we’re solving. This knowledge, will drive the new team member to genuinely care about what they’re building.

It will allow them to think in-depth about the specifics of the solution and critically question their work along the way. I want the new team member to challenge biases that the team has, and to understand and connect with the problem so profoundly that they care more about solving the problem correctly than any single deliverable.

Empathizing with the customer

This piece, is mission-critical to a successful tenure at a company.

One of the best parts about working at Shopify, in my experience, is that each employee is encouraged to be an entrepreneur. We are encouraged to start our own side-business and experience the journey from the other side. Through this experience you begin to understand the challenges that come with running a business.

By working through customer frustrations with the new team-member and trying to recreate the problem, we build empathy and find issues that resonate with us.

The primary focus of a person’s work should always be delivering value to customers. The critical piece of this, though, is understanding the gap between what you think is valuable, and what the customer thinks is valuable. More often than not, it’s easy to assume that your point of view and biases match the people who are going to be using your product, which is seldom the case.

Understand your customer and empathize with them; they are who you are building for.

Have fun

I debated on whether or not to include this as I didn’t want the end of this post to feel disingenuous, but I care so deeply about this that I felt it needed to be said: Work sucks when work sucks.

Do not stress your new peer out with office politics or other negative things. It’s not their problem. Make them smile, laugh, and empower them to understand problems and share their ideas.

Onboarding at a new company is one of the most challenging, but rewarding experiences a person can go through in life. It shapes the way you view the company, your work, and yourself. For this reason, it’s important to not only think of onboarding as a new laptop, a desk, and a password manager. Onboarding should be a time foster belonging and connection, to gain context on the team and history of the company, and to understand the impact your work will have.

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