This is the fourth post in the “How We Work” blog series. Previous volumes are available here, here, and here.

Of all the fuckups I’ve made as a founder, onboarding might be some of my finest work.

For the first 4 years, we had no onboarding. We did our little interviews, tested for “self starters,” brought people in, told them to grab an extinguisher and said “Pick a fire; any fire.”

And surprisingly that worked! For a while, and then we hired more people, only for us to ship slower. So we hired more people and it got…even slower.

Last January, when I pulled my head out of my ass editor, I realized we had:

• All the veteran people working on 4 different P0s and burning the midnight oil
• All the newer people working on P99s and sharing memes in the #watercooler channel

This was…not ideal to say the least. What happened? We used to be able to hire new people and they’d just figure out what to do?

Enter our villain — the context wall.

When I dug into our issue above, I found something interesting.

The veterans had been demolishing work on complicated stuff. Support’s real-time user infrastructure, Product’s canvas multiplayer machine, Design’s crazy complex changesets, Infrastructure’s proxy/orchestrator/etc.

These were big, hairy problems and they were only getting bigger (and hairier). However, they were working on these problems alone. Just freesolo’ing that shit. Company full of Alex Honnolds.

While this was cool to watch, I noticed two things.

First of all, there was, at best, half a person there for bus factor context.

Second, because the tasks were large/daunting, they would work around these scary tasks by knocking out stuff that could have been handled by anybody, which meant there was a lack of low-hanging fruit for others to build up that context to fix the bus factor problem.

This didn’t leave a whole lot of nice chunky projects for new hires to grip onto, ship, and feel proud of.

Without the above, the new hires went off and did other less time-sensitive things.

The ones brave enough to embark wouldn’t have enough context/reps, would end up messing something up at scale, and they’d lose the trust of the person at the top of the climb.

Our solution was actually pretty simple here — just stop polishing stuff. Anything that wasn’t a need to have became a “Good first issue/project/epic.”

Now that we had our context, enter the climbers. Wait why are they all different shapes and sizes? Oh yea they’re HUMAN. So much for those management books…

The fact of the matter is, some people have experience in specific domains. Others might want to work in different, yet equally specific domains.

Most companies don’t consider this when onboarding people. They try to figure out how to “standardize.” (The worst onboarding I went through did this. I quit within months.)

We set a really high bar, and we try to do everything in our power to get you there. That includes taking advantage of whatever helpful context you have.

So…we let you pick. Kinda.

More accurately, we make a custom onboarding plan for you as a new hire based on your strengths and desires. Here’s how it works...

Before starting, usually throughout the interview process, we figure out what you’re all about. We ask you, and we also go off your background.

The moment you sign your offer, we get to work.

We spin-up a custom channel for you on Discord. We crowdsource a Notion document.

Remember those “Good first issues/projects” from earlier, the ones the veterans left hanging around? Those go in here, based on your background and your interests.

We break onboarding down into three, 2-week chunks:

• Tasks. Straightforward tickets to get your feet wet
• Problems. More complicated problems that don’t have a clear solution
• Opportunities. Complete carte blanche to suggest “What does Railway need?”

Our goal is simple:

Nail onboarding and we trust you to tackle new problems within 4 weeks.

It’s simple to write out, but it’s really hard to execute. I will be the first to tell you that onboarding at Railway is hard. It’s hard because we have a high bar, and we raise the bar with every hire.

We choose to work with fewer, greater, people because we want to move faster, build higher, and avoid all the political BS. Fact is, most companies really break down into the hundreds of people. It becomes an “us vs them” situation.

So our pitch for Railway is thus: join us, push us to be better, and we will do the same for you.

As you go through the onboarding process, you will assuredly have questions.

Use the onboarding channel! Just ask the most random stuff you can think of. No stupid questions.

People have been instructed to help YOU succeed! Not only are you assigned an onboarding buddy and a manager, but other people will join your channel and respond to your questions.

In doing this, you will:

• Be pointed to the right channel for that discussion
• Be linked to a line of code someone will immediately apologize for
• Jump on a quick Discord voice/screenshare jam to talk about the problem

Bit by bit, all while meeting your new teammates, you’ll develop the focus, autonomy, and judgement to confidently make calls about the future of our company.

You will break something; that is GOOD.

You will make the wrong call; that is GOOD.

You will lose our money; that is GOOD.

Mistakes, made and corrected, quickly form the basis of you being able to do great work. And, above all, that’s what people want for you here; to do great work.

After 6-8 weeks of onboarding (we throw in an oncall just to keep you on your toes), you’re onboarded.

Ceremonially, you will throw your onboarding channel into the fires of the “Archived” section in Discord.

After onboarding, you have the reigns. We don’t really tell people what to do.

We have a quarterly planning meeting, where we talk about what parts of the company are on fire, we slice up the work, we dice out on-call shifts. We then fan out into project channels, and start operating autonomously to move ourselves, and our mission, forward.

You’re expected to manage your own schedule, your commitments to your coworkers, and your own time. Railway treats you like an adult, because you are an adult.

Sound interesting? https://railway.com/careers