Three ways to make the onboarding process less painful

These subtle but powerful changes to the onboarding process are easy ways to bring someone new into the fold

At most high-growth startups, it can never seem like the right time to build out more onboarding resources. When hiring is slow, it’s important but not urgent, taking a backseat to more pressing work. And when new hires are streaming in, it’s easy to say, “We really should have set something up—let’s do that for next time.”

Many years ago, I saw that while code labs and tutorials for new engineers on my team would be great, there were more foundational inconsistencies: One new hire might be lucky to get seated next to an especially helpful and not-too-busy-seeming employee. They might get to chatting, and the new hire might feel comfortable directing all questions to that person. Another new hire might be seated near people with headphones or feel a little less comfortable asking questions because everyone seems so busy.

The compounding effects of these subtle differences accumulate. One new hire might have their first bug fix or feature work open for review in just a day or two, while another may be off in the woods with no supervision or help for weeks.

Not long after that realization, I implemented a few subtle but powerful changes to the onboarding process that have worked for me since. These tips aren’t specific to any discipline or industry—they’re simply smart standards for bringing someone new into the fold.

Tip no. 1: Make a warm first impression

The first day of a new job can be daunting, overwhelming, and anxiety-inducing—so no matter how many onboarding classes or setup documents you have in place, one of the highest-impact ways you can put someone at ease is with the first impression they get when they show up for work.

I decided to set the tone by leaving a crisp, beautifully printed welcome letter on their desk with all the information they would need to get started. I went out and bought a pack of thick, creamy cardstock, and created a template I would use for every new hire.

An initial paragraph expressed the team’s enthusiasm at their joining, followed by a schedule for their first day. I included the name of their onboarding buddy (see next tip), as well as a pointer to our getting started guide to work through between meetings.

Every time a new employee joined, I loaded their first day’s schedule into that template, made sure the entire letter looked perfect (no typos or weird indentations), printed it, and signed it, “Welcome! ~Medium Engineering.”

When everything is digital, receiving something personalized on creamy cardstock is a delight (“Wow, this paper is so nice!”). Seeing the look of appreciation on each new hire’s face as they acknowledged the thought and effort that went into this personal welcome was well worth the extra 20 minutes or so it took me to put it together.

This practice was soon adopted by the rest of the company, and I passed along my hard-and-fast rules: Make sure the paper is really nice (no standard printer paper) and the formatting is elegant. In the swirl of new accounts, new people, laptop setup, and calendar invitations for onboarding events, a simple and personal reference to what a new hire needs to feel welcome and get through that first day is key.

Tip no. 2: Designate an onboarding buddy

The biggest inconsistency I found across different onboarding experiences was whether or not the new person had adequate access to someone who could answer any question they might have. In an open office, people always look busy at their desks—so if you’re not assigned someone specific, it’s easy to not want to bother people as you get set up in the first few days and weeks at a new job.

So I assigned every new hire an onboarding buddy. I’d reach out to an existing employee and make sure they had bandwidth to answer questions. Once they agreed, I’d send them an email detailing the onboarding-buddy responsibilities. Their primary responsibility for the first two to three weeks was to be available to the new hire to answer questions, direct them to the right people, etc. I also required that on the new hire’s first day, the buddy have a conversation with the newcomer and explicitly offer their assistance: “My highest priority is getting you up to speed, so even if I look busy, feel free to ask me questions any time. Even if I don’t know the answer, I can point you to the right person.”

Every new hire who was not working remotely was seated next to their onboarding buddy, even if that meant shuffling a few people on the team around. Those three things—assigning a buddy, the explicit conversation about priorities, and the seating arrangement—made new employees more comfortable asking for help. It allowed new hires to get up to speed in days instead of weeks and helped put them on a trajectory for successful.

Tip no. 3: Ask new hires about their learning style

I noticed that as companies grow, they start to codify their onboarding processes to scale. But people would come to me in coaching sessions with a problem: What worked for one engineer didn’t seem to be working for other engineers. One employee thrived under light supervision, while another needed more guidance and guardrails. One team member would ask for help from whomever was around when they got stuck, while another would go for days or weeks without a check-in.

We often assume there’s one best way to initiate people. Some people like to be thrown into the deep end with a meaty project, and others like to have their hands held for a few days. That’s not to say that you need to create a bespoke process for every new hire, but some upfront and ongoing conversations to discover how someone learns, and how they’ve successfully joined teams in the past can go a long way.

Ask a few of these questions early on:

  • What would be your ideal onboarding experience?
  • What’s a time when you felt really excited and motivated on a new project and team? What about it was most motivating?
  • What does being supported at work look like for you?

As your team scales, you’ll add more standard onboarding resources like documentation, walkthroughs, and maybe even a regular cadence of domain-specific classes. Those things are all important, but they also take a lot more time. These three tips don’t require much time to implement, are extremely high-leverage, and can effectively smooth out some of the bumps you hit as your team grows.

Jean Hsu is a cofounder of Co Leadership and a member at Berkeley’s WeWork 2120 University Ave.

Interested in workspace? Get in touch.