Onboarding: We learn through challenges, not presentations

Mar 28, 2023 4 min read
Onboarding: We learn through challenges, not presentations

By Jono Stiansen

Let’s face it: most onboarding is basically an information dump. You have to watch hours of video, which sometimes feels more like a legal precaution than an opportunity for employee learning. And you get links to a bunch of google docs, spreadsheets, or code repositories before you even understand why you need them.

There’s no context; there are no concrete goals. Instead, you’re invited to a bunch of meetings just to “sit in and absorb.”

But we can’t learn by osmosis. Our brain optimizes for the lowest glucose levels and will eject information it doesn’t quite comprehend or know how to use.

And while certain parts of onboarding need to be standardized, BetterUp managers are encouraged to continuously evolve, develop, and share new strategies to engage and empower new employees.

So in this piece, I’ll explain why I’ve spent so much time and effort on my onboarding strategy and share three main components I’ve weaved into my team’s onboarding process at BetterUp.

Why is team onboarding especially important for BetterUp engineers?

Team onboarding is particularly vital for BetterUp’s engineers. BetterUp’s general orientation is unique in that all new hires don’t actually join their team for their first month at BetterUp. As a new engineer, you would spend that time immersing in the company’s values and mission, the science behind our product, and even attend a several-day retreat (yes, it’s an incredible experience).

While our general orientation is critical to a new hire’s sense of purpose and belonging at BetterUp, it means that as a new engineer, you wouldn’t touch code for at least a month. At other companies I’ve worked for, onboarding was a slow, steady build-up to working on real projects. But I want you to build your confidence, team connection, and expertise as quickly as possible.

Another unique aspect of my team is that we mostly hire full-stack engineers and expect almost anyone to be able to work on virtually any engineering project. But that can be challenging when everything is moving quickly at a startup.

Helping you get up to speed quickly helps you prioritize effectively, make decisions that benefit our customers, and work with more autonomy.

3 key elements of the BetterUp Engineering onboarding process

The onboarding process I’ve designed at BetterUp reflects how our customers to learn. While this may not work for every squad, I believe in outlining the steps to achieve a goal and providing support to get there, ultimately placing you in the driver’s seat. This promotes our tenet of extreme ownership and accountability while getting you proficient in our codebase. Here are the three main ways my squads achieve that in our onboarding program.


Reading pages of notes, watching videos, or listening in on calls can serve as a helpful theoretical foundation. But everyone learns differently. Some people feel comfortable speaking up when they don’t understand something, and others fear asking a dumb question.

I think challenges eliminate traditional onboarding obstacles because they give you a sense of ownership over your learning, something I want to cultivate at the get-go. Learning by doing and implementing your skills within the right context quickly integrates that knowledge into your daily routine.

With that in mind, I like to focus on challenges that:

  1. Span different concepts in the codebase
  2. Involve the front end, back end, and database

The first type of task gets you acquainted with our product. Working on various features allows you to see how all the pieces fit together. The second activity ensures that you feel comfortable with all aspects of our work and enables you to become truly cross-functional team members.

Semi-structured learning

Our squads’ onboarding plans aren’t overly contrived. Things are constantly changing in a category-creating company, and we need our engineers to embrace ambiguity to make an impact. If you’re coming from a larger enterprise company, this will come as a shock, so getting you accustomed to it early is crucial.

Our squads create a general list of concepts new team members should learn as they jump into the codebase. From there, we slot in possible challenges along with rough due dates. Then, in one-on-one meetings, you review your progress with your manager.

Beyond technical challenges, we encourage you to embrace the BetterUp culture and connect with other team members and other departments by dedicating time to random coffee chats, meetings with a BetterUp buddy, and other get-to-know-you activities.


Feedback can streamline onboarding, but I’ve noticed that new hires may not have enough perspective to give feedback immediately. Just like everyone when they first start a new job, it can be nerve-wracking to expose when you’re struggling and difficult to provide constructive criticism.

So for the first few months, I meet with my direct reports three times a week. While this seems like a lot more manager-direct report interaction than new employees normally get elsewhere, I know that the sooner we can build trust, the sooner I get honest feedback and can remove obstacles in your way. I also encourage managers to ask questions like “what’s confusing?” or “what might you be struggling with?” to imply that onboarding can be tough and naturally open the door to feedback.

Better onboarding leads to better outcomes

Giving our engineers educational challenges, keeping our onboarding structure flexible, and constantly asking for feedback have dramatically improved my new hires’ time to productivity, with the bonus of reinforcing BetterUp’s emphasis on thoughtful feedback in our culture. Our goal is to help new team members like you make an impact early on in your journey, so you gain the confidence needed to be an extreme owner and practice imagination in your work.

Want a more detailed sneak peek into our onboarding process? Download my onboarding “questions to answer” here. And if you want to see it in action, apply to one of our open roles today.

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