Hiring a Remote Employee? Use This Onboarding Checklist

May 21, 2020

On March 12, we made the difficult decision to indefinitely close our office in order to keep our team safe and help prevent the spread of COVID-19. Like so many other companies, we became a remote team overnight.

Everyone who’s made this transition over the last few months knows it’s anything but easy—figuring out new methods of communication, setting up security, getting used to Zoom calls and just managing the sudden merging of our personal and professional lives is… a lot.

We encouraged our team to view this situation as an opportunity to be creative and find new ways of being the best at their jobs, instead of lamenting the many reasons why work was now infinitely harder.

But it wasn’t our tenured employees we were most worried about. On March 12, we had several brand-new team members in the middle of onboarding, three new hires who were preparing to start, and 10+ more hiring processes in the works. We had to do everything we could to make sure these folks felt supported.

We count ourselves lucky to be hiring right now—we don’t take that for granted. But hiring and onboarding remote employees is a much different process than what we’re used to. If you’re a newly remote company that’s taking on new workers in the near future, we wanted to share a couple of things we hope will help make your life (and your employee’s life) easier:

1. A checklist for onboarding new remote employees. This is adapted from the actual checklist we use at OpenView. View it in Google Docs, save a copy and customize it for your organization.

2. A behind-the-scenes look at how we’ve adapted our hiring and onboarding process and what we’ve learned from it. So without further ado:

Our remote interview process

Surely moving from onsite interviews to remote interviews can’t be as simple as sending a Zoom link? And yet… it was. Stellar candidates still shine through on Zoom.

We use a structured interview process where interviewers evaluate candidates on a specific attribute/characteristic and a firm value, and this process works just as well with Zoom.

But the piece we’ve spent more time thinking about is how to build the relationship with the candidate and ensure our culture comes through loud and clear.

Our quick tips:

  • Treat your Zoom “onsite” time the same as you would with an in-person onsite meeting. Don’t spread interview sessions over multiple days—just block the whole time and let the candidates immerse themselves.
  • Set up one Zoom room for the entire interview so that the candidate doesn’t have to go from one link to another. This helps avoid technology glitches, confusion or having interviews run past the scheduled time.
  • Make sure you offer breaks. Just because you’re online, it doesn’t mean candidates don’t need a few minutes for a bio break, a coffee refill or a quick snack.
  • Schedule an internal debrief meeting on Zoom. Stick to your normal hiring processes—don’t let Slack or email take the place of a live debrief just because it’s easy.
  • Prep the candidate at each step. As a hiring manager, I always like to prep candidates for the conversations they’re going to have, but this is even more important in a remote environment because it allows you to become their ally and help them through the process.
  • Start texting early. Moving conversation from email to text allows you to be more casual and have more regular connection points.
  • References are more important than ever. With virtual interviews, you miss out on some of the nuances and potential red flags you get from in-person interviews, but references can play a huge role here. Supplement the candidate’s references with backdoor references you source on your own for an objective perspective.

It’s okay to hire someone you’ve never met in person

When we flipped to remote work, we were in the middle of the interview process with some great candidates who’d already visited our office, but what about the people we hadn’t talked to yet?

We quickly agreed that we could hire someone we’d never met in person—something we’d never done before—but the question was if we would.

Related: The Ultimate Remote Work Resources Guide

Turns out the answer is yes. Jacob Suh joined us a couple of weeks ago as the newest member of our investment team. He lives in California and will eventually move to Boston to join us in person—sight unseen.

We learned a lot through this process about how we interview and how we get to know someone. A couple of big ones:

  • Book more time for each interview to ensure there’s plenty of time for the social side and for building rapport.
  • Make sure the candidate gets to meet peers and not just senior members of your organization. They need time to ask peers questions, and you need to get feedback from those folks about cultural fit.

Remember to keep an open mind as you adapt to a “new normal.”

Onboarding remote workers

I got to put this one to the test right away. With two new hires slated to start on March 16, we were forced to rebuild our onboarding plans on the fly to adapt to an all-remote environment. Here’s what’s working for us:

Ship/courier equipment ahead of the start date and ensure your new team member is set up from day one. Consider whether your standard new hire setup is still appropriate or if you need to coordinate on developing a home workstation.

Get aligned internally on what success looks like. If you’re all aiming for the same goals, you’ll help your new hire get there faster.

Share a structured onboarding plan with your new hire that includes:

  • Overarching goals: What does success look like?
  • 30-, 60- and 90-day SMART goals: What tactics will allow them to reach the goals you’ve agreed to?
  • Training sessions:
    • Company: History, values, team overviews
    • Industry: Market context, competition
    • Role: “How to” sessions, practice, documentation and shadowing

Direction for downtime: Help them fill their time for the first few weeks as they get up to speed. You can’t schedule every hour of the day, so what does downtime look like for their role?

Assign a buddy (or two)! Our investment team has a manager, a mentor and a buddy involved to help each new hire. Make sure the new hire knows who to turn to with day-to-day questions.

Figure out what your communication plan looks like—especially for the first few weeks knowing you can’t just swing by his/her desk. Some ideas:

  • Create a private team Slack group: Enable new hires to “ask anything”
  • Morning stand-ups to kick off and prioritize each morning
  • Daily wrap-ups to reflect and cover any outstanding questions

We don’t pretend to have all of the answers, but we’re learning and iterating quickly. Please share any ideas with us.

In case you missed it above: We created a free checklist for onboarding remote employees to make it easier for you to remember equipment to order, trainings to schedule, software licenses to purchase and much more. Save a copy, customize it for your organization and brace yourself for a whole lot of virtual high-fives.

More remote work resources

How to Keep Your Company Aligned While Your Whole Team Works Remotely
5 Tips for Better Remote One-on-Ones
How to Stop Having So Many Remote Meetings

Liz Cain


Liz Cain leads the firm’s Investment team and sits on the Investment Committee. Liz joined OpenView in 2016 to lead the Expansion Platform delivering recruiting, market insights and marketing/sales strategy services to our portfolio. Today, she manages the Investment team and focuses on developing the systems, processes and team to identify and win the best expansion stage software deals.