Onboarding Remote Employees

remote onboarding

If you had told me in 2019 that in the following year I’d be hiring a VP Sales without ever meeting him in person, I would have burst out laughing.

Fast forward to 2020, and with the world in lockdown but business continuing, my team at Crystal doubled our headcount while operating completely remotely. Once the hires were made, we were left with the critical task of getting them up to speed and productive as fast as possible, all while working from home.

As I thought more about the task ahead, I recognized perhaps the most crucial difference between remote and in-person onboarding:

  • In person, when your new employee has a complex question, it’s really easy and socially acceptable for them to walk over and ask you.
  • Remotely, when your new employee has a complex question, they need to take the initiative to call you, or put the effort into wording it the right way in Slack.

The dilemma with remote onboarding is that when someone is confused, the barrier to getting clarity is much higher. When we’re in person, they can casually walk over to someone’s desk and get an answer. When we’re remote, suddenly those quick answers require more effort — either through calling or instant messaging, and the social friction required to do both. Especially for someone brand new, it is much harder to call a colleague (or even Slack a colleague) out of the blue vs. just walking over and talking to them.

As a result of this, we need to take a different approach to remote onboarding. From personally testing this strategy across several key hires, here is a breakdown of 6 best practices to take when onboarding a new employee remotely.

1. Create an onboarding checklist

The nightmare scenario of remote onboarding is your new employee is sitting at home, unsure of what to do and unsure of who to ask for help. At that moment they feel isolated, unproductive and unmotivated. To avoid this, the best tool in your toolbox is an onboarding checklist.

The onboarding checklist is a shared spreadsheet that outlines everything someone new should read, participate in, talk to etc during their first days/months of being at your company. Here’s an example of my checklist:


Notice that the checklist includes everything from the very tactical payroll configuration to the very specific “explore X feature in the product.” The goal of this checklist is to act like a virtual guide for the new hire, which they can consult anytime, 24/7, to answer the question “what should I do next?”

Remote employees get the consistent dopamine hit of “checking off” each item and seeing the green “completed” label next to it. Managers get the benefit of transparency and clarity on a new employee’s onboarding status.

2. Create a first-day agenda hour by hour

Everyone remembers their first day at a new job. When that first day is entirely remote and we don’t have the option to create memories like taking a new hire out to lunch, we need to put even more focus into the structure and cadence of the day. To do this, create an agenda for that day that breaks down exactly what the new person should be focusing on. It should include:

  • An intentional first meeting of the day with their manager to kick things off
  • Invites to relevant training sessions or meetings to shadow
  • Specific reading material (based on the onboarding checklist)
  • An end of day recap with their manager to discuss and concerns, and plan day 2

While it might seem like excessive structure, creating an agenda that breaks down each hour of the day ensures that the new hire can be productive and operate without the pressure of essentially “cold calling” their colleagues in order to become productive.

3. Grant access to accounts in advance

Nobody should ever begin a new job without the tools they need to immediately start creating value. Especially when someone is remote, if they don’t have access to their computer and relevant app accounts, they are pretty much blocked from doing anything.

Consider adding a tab to the onboarding checklist for “accounts” and list out every app that this person should have access to, and who is responsible for configuring access. Ensure all of those are checked off prior to the start date, and credentials are emailed to the employee’s personal email so they can log in prior to their first day if they’d like.

The goal is avoiding any time where a new employee is twiddling their thumbs at home. Taking care of account access in advance demonstrates that you value their time.

4. Over-communicate prior to starting and during the first week

Most people have a mixture of anxiety and excitement leading up to starting a new job. Especially for startups, ambitious hires will want to hit the ground running and start preparing prior to their start date. Particularly for more senior hires, I prepare all of their onboarding materials (including the checklist and account access) well in advance of their start date. This way, they are free to start reading key documents, exploring their new accounts (e.g. our CRM) and formulating questions that we can tackle during their first week.

You may also consider doing a weekly call between the time they sign the offer letter and their start date. I use this time to keep them updated on important developments at the company (e.g. closed a new deal, made an additional hire) so they are in the loop when they start. Furthermore, finding opportunities to communicate starts to build that rapport and trust needed to make them comfortable and productive on day 1.

5. Split up heavy video call sessions into manageable chunks

Most remote onboarding sessions happen over long video calls. That is totally ok, and consider splitting up those calls throughout the day to avoid fatigue. As you outline the first day agenda, consider intermixing different activities such as team 1-1s, direct training sessions, solo reading and silent observing in other meetings. While some of these activities are similar to what you’d do in-person, the reality of remote is that it is easy to get “meeting fatigue” on video, so putting extra thought into how you split up onboarding activities makes a positive difference for the new employee.

6. Plan on daily check-ins and an end of week recap

In addition to over-communicating prior to start, remote work onboarding requires heavier communication during the first days and weeks. To overcome the “barrier to getting clarity” hurdle mentioned earlier, you should provide many opportunities for a remote employee to ask questions and get “unblocked.”

My approach is that typically in our first meeting, while reviewing the first day agenda and onboarding checklist, we create a running “Q&A” list at the bottom of the agenda. The employee can continuously add questions, and I periodically review the list, make comments with answers and discuss the complex ones at our daily check-ins. My aim is for the employee to never have to wait too long to get clarity and be left in the dark remotely.

We punctuate the week with a recap meeting that is similar to the one held at the end of the first day. We should enter the weekend by recapping the momentum made in the first week, and ensuring the new employee is making progress in accomplishing their 30/60/90 day plan.

Bottom Line

Remote onboarding requires extra consideration because of the challenges of quickly getting clarity when not in-person. By using a mixture of staying organized through an onboarding checklist and communicative through pre-start, first day and first week check-ins, you’ll be much more likely to set up remote employees for success.

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