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Onboarding Remote Employees: How to Do it Right & Avoid Costly Mistakes

Learn to avoid the most common missteps of onboarding a remote team.


Everyone’s favorite human resources subject! (We kid). Onboarding isn’t the most exciting of topics. But it’s an important one.

You have a goal: to effectively get your new hire up to speed as quickly as possible so they can begin the real work. The thing is, most people are going about this in the wrong way, and it’s costing them.

They focus on speed, not quality. In any setting, this is ineffective at best and toxic at worst. But when you’re onboarding remote employees? It’s downright wrong and, dare we say, ignorant.

Having onboarded hundreds of virtual employees over the past two decades, we have a certain system that not only brings them up to speed, but ensures when they start work, they’re doing it from the right place.

Everyone Wants One Thing With Onboarding

You want to get your new hire up to speed and working in their new role ASAP. It’s the most cost effective. The sooner they get to work, the sooner they’re providing your business with value, right?


Here’s what typically happens when you hire a new person:

  • You give them a brief on their role and have them sign all the appropriate documents
  • You get them logins to all the project management tools they’ll need
  • You ask if they have any questions
  • They say “Nope, all good!” because they want to seem like a great hire who needs for nothing (and they also aren’t sure what they don’t know yet)
  • They end up struggling and taking excessive time to get up to speed and are often lost with what to do, where to go, and who to talk to for their role
  • You sit flabbergasted that the “perfect hire” you thought you got seems to lack a work ethic

This process happens all the time with remote employees and it overlooks the more important pieces of onboarding that guarantees when they do begin their normal work, it’s done at an effective level.

If you’ve recently made the switch to remote work from in-person, you’ll have to watch out for even more challenges.

The Difference in Onboarding Remote Employees v. In-Person

Getting someone up to speed in the office is much different than remote work. It’s like going to a buffet versus hiring a private chef. Sure, you still eat either way, but the entire experience and quality of the meal is different. In-person onboarding at the office is full of people available to help, say hello, and chatter in the company lingo. Don’t underestimate how much this environment informs newbies.

But here’s the thing: you do still have to make sure your new employees are set up well in a remote company. The main difference here isn’t what most think.

The challenge in onboarding virtual employees isn’t making sure they get the access they need to all the programs.

It’s not teaching them the ins and outs of their new role.

And it’s definitely not making sure they know your company’s handbook inside and out.

The biggest difference in remote onboarding is much more overlooked: It’s team integration.

Out of sight, out of mind. This phrase ring a bell? It most definitely applies with new employees in a virtual work setting and can be the single biggest cost related to new hires.

Imagine you just got hired and you’re sitting in your home office, logging on to your company’s project management software, going about your normal day when you encounter something you don’t really understand.

Who do you go to?

What does it even mean?

Can you just jump in with the rest of the team and ask without looking dumb?

These seem like simple questions. They should just ask their supervisor! Right? No. Because new hires usually don’t want to look like they don’t know something that they’re supposed to know. They’re insecure about asking—because they’re human.

It’s not their job to ask a thousand questions to become integrated with the team. It’s your job to set them up for success from the start.

How to Onboard Remote Employees Successfully

You can find a hundred “how to onboard remote employees” lists online, all sharing similar information about culture and handbooks and moving quickly. While they’re not necessarily wrong, they’re also missing some of the most important pieces.

So, how do you do onboarding virtually then?

We already covered a specific 30-60-90 Day Plan for onboarding that has screenshots and a schedule, so we’re going to skip over that and focus on the important pieces to build within that plan.

This is our guide for onboarding remote employees based on our successes and failures over the past 20 years of working remotely.

1. Inform team and update projects

You won’t see this piece of advice in many places. Onboarding a virtual employee is just as much about getting the whole team involved as it is getting your new hire up to speed. If they don’t acknowledge that there’s a new person, know their face, and know their role and how it integrates with their own (especially for current in-progress projects), then your new hire has little hope of success.

Make an announcement, host a meeting, and have your current team know who that person is and what they’ll be doing. You never want a new hire to feel like a stranger or for your team to not know you’ve even hired someone.

This includes resetting expectations for any projects your remote employee will be hopping into that are already in-progress.

2. Set up an onboarding workflow

This doesn’t need to be crazy. There are remote companies out there with massive projects and fifty to-dos on their new hire’s list before they’re even allowed to begin working. That’s not necessary. What is necessary is creating some sort of workflow so they know how to get through onboarding information.

Using this 30-60-90 day plan template is a great way to create structure without reinventing the wheel.

Sample onboarding workflow we build in our Basecamp 30-60-90 Day Plans
Sample onboarding workflow we build in our Basecamp 30-60-90 Day Plans

3. Introduce the team

The very first thing for onboarding a remote employee should be familiarizing them with your existing team. Allow them to get to know everyone, talk, and meet “face to face”. This ultimately opens a door for your new hire to feel comfortable with everyone so they can ask questions when they have them.

There’s no need for corny ice-breaker games here. This forced-intimacy usually makes virtual employees more uncomfortable than included. Keep it authentic and allow people to bond as they will naturally.

(Psst… looking for a place to keep all your remote employees connected? Try the all-new Basecamp. With group chats, private messaging, file sharing, message boards, to-dos, and more, you have everything you need to keep your remote teams on track, all in one place. Get started today for free - no credit card; no commitment)

4. Have them review existing content

Instead of onboarding a remote employee with PDFs that do a terrible job of expressing your company’s culture and a handbook that we all know they’re not going to read, have them review all of your existing content.

If your new hire doesn’t fully understand your content (and the customers it was created for), how much confidence do you have in their ability to perform their job well — no matter what their position is?

Prioritize this. This review process should include:

  • Internal podcast episodes or podcasts your founder has been featured on
  • All products and other programs
  • Any online communities your company hosts
  • Popular content: blog posts, social media, emails

You may think this is overkill, but the best new hires are the ones who get what you’re about. What speaks to that more than what you put out into the world?

5. Walk them through a day-to-day workflow

Even if your company is similar to the one your new hire previously worked at, the way you operate might not be. It’s a mistake to assume they’ll just be able to step into your day-to-day flow without guidance.

One of the best things you can do is have them shadow someone in a similar position and walk them through how a typical day goes. Of course, there will be differences. Make sure they know they can tweak and adjust their workflow to make it their own, just don’t leave them hanging. Provide that framework so they’re not clueless.

6. Ask them how they work best

You’ll have a feel for this after their interview, but make sure to double check how they work best. You don’t want to leave a high-collaborator alone to figure things out but you also don’t want to assign an independent introvert with multiple meetings right away.

Accept that different people have preferences and adjust how you onboard accordingly. The goal is to support each individual new hire, not create a system that is exactly the same from start-to-finish.

7. Check in consistently

As mentioned previously, not all new hires will ask questions when onboarding. They want to put their best face forward and look like they know what they’re doing. But you can be proactive in checking in and asking if they need anything. They’re much more likely to answer a request than to be the one bringing you a challenge.

Doing this actually sets the tone for how you communicate at your business.

8. Ask for feedback and iterate

You won’t always know what’s working and what’s not. Let’s not just assume things went well. Choose a date and create a to-do so you’re reminded to ask for feedback about the entire process once your remote employee is fully in the throes of their new job.

Make sure you ask specific questions instead of just, “any areas of improvement?” You’ll get more honest answers.

Here are some questions you can ask to improve your remote onboarding:

  • Do you feel confident that you could explain to a stranger how we operate here?
  • What made the way we do things “click” for you?
  • Who was most helpful during the onboarding process for you?
  • Were any areas confusing to you?
  • Any thoughts on what would be most helpful to new people hired in the future?

Onboarding might not be the most fun thing to strategize about, we get it, but the first 90 days of a new hire’s experience can impact the rest of their working relationship with you. With so many businesses making the switch to remote or a hybrid working schedule, make sure you don’t assume all of your in-person processes will still work.

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