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What We’ve Learned from 6 Years of Onboarding Remote Employees

3 November 2020

Principles and specific tactics that we have seen work well.

Starting a new job, becoming productive, and plugging into a company culture is a challenging experience even in an office surrounded by supportive co-workers. In a remote setting, however, you are doing it sitting alone in your home through a computer screen. If not well-planned, once the first couple days of HR onboarding and intro Zoom calls have died down, you might find yourself sitting alone unsure of what you should be doing or hesitant about pinging people on Slack repeatedly with questions.

Research shows that organizations with strong onboarding improve new hire retention by 82%, productivity by 70% (Glassdoor), and engagement by 55% (SHRM). And onboarding well is much more challenging and more important in a remote setting.

We’ve run our own firm as 100% distributed since we founded it six years ago, so we were forced to tackle this challenge from the start. (On a related note, see our earlier piece on hiring remotely, How to Hire Someone You’ve Never met in Person.)

Even after we get through this crisis, the increasing popularity of remote and semi-remote models means that remote onboarding is a skill that many companies will need going forward. And even for companies that shift back to in-office work, the same investments in greater structure that support remote onboarding will make in-person onboarding more effective as well. 

This article lays out some of the principles and specific tactics that we have seen work well.

  1. Send Some Stuff Before Day 1
  2. Go Deeper on Tech Setup
  3. Invest Heavily in Documentation
  4. Build an Onboarding Plan that Goes Wide and Mixes it Up
  5. Pack the Schedule, Assign a Buddy, & Involve the Team
  6. Track Progress and Competency
  7. Loop Back & Learn

 

1. Send Some Stuff Before Day 1

It’s important to send employees both critical and welcoming items in advance as physical manifestations of their new job. Companies that provide computers should make sure they are ready and set up. Additionally, it’s good to send items that help with home productivity like a second monitor or webcam. You can send books relevant to the industry, role, or company culture (go physical, not Kindle). A care package or gift basket of some kind can be a nice touch and some companies send a Postmates gift card to buy lunch on your first day. Finally, company swag like a mousepad, coffee mug, or a hoodie can also bring a little of the team’s identity into the home.

2. Go Deeper on Tech Setup

Most companies have some kind of basic tech checklist when it comes to setting up email accounts and core SaaS tools, like HR systems or the company’s CRM. But in a remote environment, the pile of SaaS apps we throw at our employees aren’t just supporting tools, they are literally the medium through which the employee experiences their job. So the details matter and it’s worth going a couple levels deeper to avoid employees spending weeks discovering various gaps and settings ad hoc.

First, make sure you cover ALL the tools they will need for their job. This could mean a secondary SaaS tools like a niche campaign management tool or research database that only some of the team uses. Develop a comprehensive list of all the tools that ANYONE on the team uses and then you can edit it down to the subset for each person. Also, using a password manager (Dashlane, LastPass, 1Password) is a great way to manage setup and access in a smoother and more secure way.

Next, go one level deeper on providing details around settings and configuration. This may sound dry, but these become friction points that make getting started more complex and puts the employee in the awkward situation of repeatedly asking teammates for help which can feel more like an imposition in a remote environment. 

Just to get specific, here are a few examples:

3. Invest Heavily in Documentation

In many companies, after their “Day 1” HR setup, the employee is just dropped into their group where the rest of onboarding becomes some mix of apprenticeship and osmosis. This might include a few intro sessions followed by initial tasks, attending meetings, and being around people as they do stuff.

In a remote environment, companies need to capture the processes and activities that make up the job in more detail. You want to capture as much of the tribal knowledge that lives inside people’s heads or in norms that new hires just “just pick up.”

This documentation then becomes the foundation for a detailed onboarding outline that maps out ramping into the role. It should cover roughly the first three months for the employee, break out the different parts of their job, and assign training and partnering roles to other team members.

This agenda provides a clear reference point of expectations for the employee and greater emotional comfort that their time and activities are mapped out. For the rest of the team, it creates accountability on who’s doing what and visibility on what context the employee does or doesn’t have so far.

From a tactical perspective, we use a multi-tabbed Google Sheet for this. The first tab covers the day 1 Admin, HR, and tech basics and then subsequent ones cover first weeks and months with sessions broken out by subject, goals, links to docs, and participants. You can use other online tools like Asana or Trello as well, but the more online and flexible your documentation is, the better. 

Most organizations use some form of modern cloud-based document tool (Google Drive, Dropbox, Box, Sharepoint) which all have advanced search and URL links to each file, allowing you to create nice cross-links and a “table of contents” to organize key docs. You get greater transparency and access to information for everyone and you save the new employee having to ask people for docs repeatedly or go on archeological digs through messy directory file structures. This also gives a new employee options for reading and exploration when they do have quiet time. You’ll need to assign someone to organize and curate these docs over time as things inevitably get messy over time if left alone, but it’s worth the investment for both onboarding and productivity of the entire team.

4. Build an Onboarding Plan that Goes Wide and Mixes it Up

Think through “a week in the life” of a role and the various workflows, activities, and deliverables. Depending on the role, this includes activities like analyses, presentations, sales calls, product deliverables, campaign optimizations, internal meeting prep, reporting, etc. Think about both the regular and ad hoc activities that go into each role. You’ll never capture everything and roles change over time, but you should be able to outline 90% of what typically happens. 

It’s also worth thinking about what kind of context and foundational knowledge is needed to lay the groundwork for these activities. Company introduction, including history, mission, values, org are all key. Then you can ladder down to areas like industry context, customers, competitors, your own products and go to market strategy. These are the kinds of topics that are often learned “around the office” by dropping in on conversations and meetings, but you need to design for them explicitly in a remote world. 

It gets dry and tiring to learn everything by having it told to you in many training sessions (especially over Zoom). So it’s good to vary the formats and settings in which all this information is delivered. This could include:

5. Pack the Schedule, Assign a Buddy and Involve the Team

Once you have your detailed outline, be aggressive with filling the new employee’s calendar. In person, dead time can be filled by looking over someone’s shoulder and colleagues can see you’re just sitting there and pull you into a meeting, but it’s easy to feel isolated or adrift when at home alone. So overcompensate on planned sessions and even in between, you can assign lists of specific documents to read as part of training. 

Assign one person to be the new employee’s buddy or “onboarding coach.” They are the owner of the overall onboarding plan. This could be their manager or a peer depending on what makes sense. This provides a first point of contact for questions and can help adapt the plan and fill in gaps as well.

Another nice tactic is to split up the onboarding duties across the team. It’s an organic way to meet more people in the company and have people exposed to new team members right up front. In a remote environment, people may not collaborate or be on a project together for a while, so months could go by without a chance to really connect.

People also have different learning and communication styles, so hearing about new subject matter areas or training topics from different people can be a better way to absorb knowledge. Finally, it can be a nice development opportunity for team members giving the training. 

6. Track Progress and Competency

The onboarding outline should track progress and have accountability. Have a checklist against the core abilities and activities. Rather than just showing them once and hoping that they got it, you can track proficiency with a little more structure. We use a matrix something like the following: Introduced/observed, Can do with partner, Can do Independently, Can do Proficiently. This is great for the employee in understanding what is expected of them and creating a sense of progress and success in their onboarding. Equally important, it sets expectations among the rest of the team as to what the new employee is capable of and their readiness to contribute in each specific area of the job. 

7. Loop Back & Learn

It’s important to think across multiple time horizons beyond the typical “week 1 setup.” The onboarding plan discussed above gives you the structure to think about the first weeks in great detail, and expand to follow ups and check-ins over the first few months.

Checking in is even more important in a remote setting. You won’t see the new employee looking confused, busy, lonely or whatever they are feeling at the end of the day. Build in touching base on how it’s going — we assign a check-in at the end of every week. It’s a good time to calibrate and tune your plan. Are there too many meetings, not enough? Are there specific questions that have come up? Some could be quick answers during the check-in, or might lead to adding a follow up session to the plan. 

In our onboarding plan, we have the first 2 weeks mapped out an hourly schedule level. Then the rest of month 1 with more space as people join in to regular meetings and activities. Then month 2 and month 3 ramp into a lighter formal schedule with weekly and monthly milestones.

We also try to build in some repetition and recap on key subjects. No one remembers everything after hearing it once and the same topic means more after some additional context or seeing it happen “live” in meetings, customer interaction, or hands on execution. Each organization can assess which fundamental topics are worth that repetition.

Finally, use each onboarding experience to gain feedback and iterate. No matter how much time you put into the initial plan, there are topics and sequencing that will get missed.

We target three months as the milestone where people should be up to speed. At that point, we’re asking employees how it’s going, confirming that they feel ready, and if there are areas they don’t understand or where they want more time. 

Then, about 6 months in, when someone is up to speed and fully rolling with their job, it’s a good time to get retrospective feedback on their onboarding. Now that they are up to speed, looking back, what would they do differently in their onboarding? We’ve received good feedback that’s led us to invest more in certain areas, less in others, and even change the sequence in which we cover topics. 


In summary, the same tactics and principles that make for strong onboarding in a remote environment will serve you well in general. The most recent generation of productivity and collaboration software provides a more flexible toolkit for developing documentation and workflows. More broadly, we’ve found that being forced to break apart a job’s components have led to insights around role definition. By thinking holistically about what a new hire needs to succeed, you can develop an onboarding program that delivers the training they need, and does so in a way that introduces them to more colleagues and makes them feel a part of the team culture.

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