Learning is a cornerstone of success everywhere. It has no time limit or age restriction. There's no progress without it.

So how does a company create an environment where its people read, test, observe, reflect, think, learn and iterate because they want to? How do you foster a culture of learning?

On our mission to bring insurance to the internet, we have to navigate unknowns, rewrite rules and rebuild legacy systems. There's no way to achieve that without learning constantly.

In this third article of our culture series, I want to share a few practical ways we keep learning at the heart of everything we do here at Root. By creating spaces where we can share and grow together, work becomes infinitely more enjoyable.

Our 5-whys process

Having a culture of learning is important when you’re building an industry-leading company. That means learning from your mistakes.

We do everything we reasonably can to blow our clients away. Our clients are large companies with thousands of customers who rely on them every day. The stakes are really high, and sometimes we make mistakes.

When something goes wrong, we don’t point fingers or throw one another under the bus. We have a 5-whys session, where all the people involved in the project get together and determine what went wrong – and how to prevent it from happening in the future – by asking why at least 5 times. This is a great root-cause-analysis approach, and allows us to focus on the processes that broke, not the people that made the mistake, since we always assume good intent.

Failure is a great way to learn.

After something goes wrong, you want to do a 5-whys session as soon as possible. Fix the burning problem, and then do a 5-whys. Every subsequent “Why?” should lead you to a more fundamental problem. The team doing the 5-whys might end up with something as follows:

Root 5-whys example

Learn more about doing effective 5-whys here on Kanbanize.

We’re big on reading

We share books with each other and chat about the stuff we learn. We’re building a library in the office, and watching it grow as the team fills its shelves has been brilliant. You’ll find books about tech, management, product development, and start-up culture. And when you need a break from active learning material, you’ll find books like Ready Player One or What If?

Our library grows exponentially as more people join the team. It’s a Root tradition for a manager to gift a book to any new team member when they hit the three month mark at the organisation. We’ve found it a great way to introduce team members to our learning virtue.

Some of the books we find valuable on the subject of learning are:

Virtual learning spaces

Slack plays a major role in how we work at Root. We use it to communicate transparently and collaborate with partners. We also use Slack to create virtual spaces to chat about projects and learnings. Some of the channels dedicated to learning at Root are:


We have a curious team, so this channel pretty much started itself. Everyone is big on self-improvement. We know that to make Root great, we need to learn as much as we can from one another. Diving into the books our colleagues love is an awesome way to do that, and we get to know each other better.

We kicked it off by reading one book a month from this Goodreads list and then chatting about it together as a team, and it evolved super organically from there.


This is one of the most active channels in the company. It’s where we share industry knowledge with each other. Any article, report, thought leadership piece or TED Talk that’s relevant to our business or mission is shared here – including Starship launches or the latest VR product release. Insurtech moves fast – this channel helps everyone stay in the loop and on our toes.


We’re a company that builds tools for developers, but not everyone at Root is an engineer. We find it important to give everyone else in the team the chance to learn how to code.

The #academy started out as a selection of Udemy courses that any non-technical person can follow, and evolved into a collaborative learn-to-code space with coaching support from the broader Root engineering team.

We work primarily with React, Node.js, TypeScript and PostgreSQL across our engineering teams. The #academy covers the basics across all those programming pillars and allows everyone to speak the same language, whether you’re an engineer or a finance manager.


“Lunch ‘n Learn” sessions are a moment for the team to bond over lunch and listen to a colleague or special guest talk about something they’re very knowledgeable in. It’s a bit like an informal Ted Talk, with way fewer formalities and way more delicious food. These sessions give us the space to discuss interesting topics and stay inspired.

We’re looking for awesome people to join our team

If our learning virtue resonates with you, look at our careers page to see if we have a role open for you. If not, you can apply anyway by selecting “Don’t see a role for you?” and we’ll get back to you when something suitable opens up!