Onboarding and Training in a Remote Team

It’s daunting.

When you’re not in the same physical place, you can imagine how someone new joining your team might feel. You need to find a way to make sure everyone can feel well-equipped and confident to contribute to the team, without being with someone in-person. It’s a challenge. After all, the numbers on how likely it is for a new employee, regardless of where they are located, to leave within the first 90 days are astounding: 30% employees leave before their first three months are up, according to a survey with 1,500 people.

As a result, it’s imperative to give new hires the exposure, resources and support they need to be successful – particularly when remote. To do this, remote managers often focus on having a strong, hands-on onboarding process. In fact, according to our survey, 69% of remote managers said they had a formal onboarding process, while only 59% of in-person managers who said they had a formal onboarding process.

From the insights of 1,000+ managers in our online leadership community, The Watercooler in Know Your Team, I noticed clear commonalities for what leaders view as best practices for how to onboard a new hire. Interestingly, when I reviewed these best practices, they don’t necessarily only apply to remote teams — they equally are relevant and applicable to in-person teams too. Here were the most frequently cited elements of their employee onboarding processes:

  • Mentorship – At many companies, new hires are usually paired with the lead as a mentor (or a more senior person). Oftentimes, this is a formal buddy or mentorship program. For remote teams in particular buddy programs seem to occur with greater frequency than in co-located teams: According to our survey, 51% of remote managers said they have a mentorship program or “buddy system” as opposed to 41% of in-person managers who answered the same way. An example of a company that does this is Help Scout: They give the new hire a buddy or a new “work best friend” on their first day of work.

  • Partially in-person onboarding – Because bringing a new employee up to speed can be tricky, some remote companies will partially onboard their team members in person. When we first brought on my business partner and CTO Daniel Lopes, here at Know Your Team, that’s what we did – we worked together in-person in Chicago for about a week or two. Wade of Zapier, similarly explains how they onboard new hires by bringing them to the same location as their managers for a period of time. He calls it “AirBnOnboarding”: “AirBnOnboarding, which when we hire folks within the first month, we actually do like to have them spend a week in person out here in the Bay Area. So we’ll rent an Airbnb, we’ll bring their manager out here, them out here and then spend a week working alongside them.”

  • Weekly one-on-ones – During the first month, the new hire often has weekly one-on-ones with the lead/mentor (and a couple with the CEO as well) via video chat. After the first month, the one-on-ones slow down to a more moderate pace, such as biweekly or once a month. Below are some of the questions that I asked Mandy, one of our new hires who is remote (she lives in Pennsylvania):

    • Personal connection
      • How’s life?
      • What are you excited about lately?
      • Anything have you worried or down lately?
    • Issues
      • When have you felt frustrated in your first 2 weeks here?
      • What feels unclear? (E.g., Do you feel you have enough context about the company?)
      • How clear is “success” for you for the next 3 months, the next 6 months, and next year?
      • Are there any decisions you’re hung up on?
      • Observations about the team and/or company culture?
    • Feedback
      • Would you like more or less feedback on your work?
      • Would you like more or less direction from me?
      • How is the workload?
      • What aspect of your job you would like more help or coaching?
      • What about my management style can I improve?
    • Career direction
      • If you could be proud of one accomplishment between now and next year, what would it be?
      • What’s one thing we could do today to help you with your long term goals?
  • Nailing the basics – Many remote companies have thorough, rigorous documentation that explains processes and details like getting their computer all configured. For example, the company MeetEdgar has an elaborate employee handbook where all their processes in the company from vacation to communication are outlined. For our new hire at Know Your Team, I wrote “Welcome note” that I include in its entirety below.

  • A clear first project – One recommendation is to design what the first month of the new hire will look like for the project(s) they’ll tackle. What will they be responsible for, and what’s the ideal outcome? You want to have something to help the person get acquainted with the company, but also have the feeling of accomplishment at the same time. (I also did this for our new hire.)

What I did for our employee onboarding process

Something new happened recently: We hired a new employee at Know Your Team – and it caused me to rethink our entire employee onboarding process. As a small, profit-focused team, we don’t hire often. As a result, this time around, I wanted to be intentional about how to onboard a new hire.

Given the consensus around these recommendations on how to onboard a new hire, I incorporated these elements into our own employee onboarding process. However, I also knew from our research through Know Your Team over the past 5 years with 15,000+ people, that as a leader, it would be crucial to provide our new hire with (1) as much context as possible about the business itself (2) direction as to what “success” looks like (3) encouragement in carrying out the role, and (4) a sense of rapport and trust so that we can work well together.

As a result, on our new hire’s very first day at Know Your Team, I sent her an Icebreaker through our software (it’s a set of fun questions that help break the ice).

I also wrote up a “Day 1 Welcome Note” and sent it to her. We’re a remote company, so we default to written, asynchronous communication – but I also wanted something in writing she could refer back to, if needed.

Here’s what the “Day 1 Welcome Note” included…

Why we hired you – When you tell someone why you hired them, you’re essentially saying to them: “I believe in you.” Few forms of encouragement are better. You show your support for them on Day 1, and simultaneously set your expectations for the things you want them to continue doing. Not to mention, I’ve always found it strange when you join a new company, and you’re not exactly sure why they picked you.

Context write-ups – “What are all the things someone new has no clue about, but would love to know?” I asked myself that question, and then wrote up a series of documents that attempted to answer it as much as possible. The result was separate documents on our company’s history, our purpose + vision + values, how we work (communication, meetings, etc.), business context (market analysis, product vision, etc.), and the key milestones we’re looking to hit in the upcoming six to eighteen months.

Work preferences survey – Annoyances, pet peeves, proclivities, and communication tendencies… I wanted our new hire to have an opportunity to share all those things about how she prefers to work. And I wanted her to know what everyone else on the team’s work preferences were, too. And so I wrote up a survey with 23 questions:

  • Where on the spectrum of an extrovert to an introvert would you place yourself?
  • What’s your preferred way to receive feedback, in terms of format?
  • What’s your preferred way to receive feedback, in terms of speed?
  • What’s your orientation toward conflict?
  • What time of day are you most productive?
  • How would you describe your communication style?
  • What motivates you the most?
  • Who is your hero? Why?
  • What do you value, more than anything else?
  • What do you consider your “superpower”?
  • Who’s been the best coworker / team you’ve worked with? Why?
  • Who’s been the best boss / mentor you’ve ever had? Why?
  • When have you worked with someone and noticed it not going well?
  • How do you tend to organize your work day?
  • How do you tend to organize your week?
  • What do you think you’re more sensitive about, compared to others?
  • What do you tend to have a longer learning curve around, compared to others?
  • What do you tend to pick up very quickly, compared to others?
  • What’s your biggest work-related pet peeves (i.e., that thing other people do that totally annoys you when you work with them)?
  • What does “work life balance” mean to you?
  • What would others who’ve worked with you say are your greatest strengths?
  • What would others who’ve worked with you say are your greatest weaknesses?
  • Anything you’d like to share about what makes for your ideal work environment?

After she filled out the survey, I then shared with her everyone else’s responses – and I made sure when I filled it out that I didn’t look at her responses either, as a means to not be swayed in any way.

Definition of success and potential projects – As suggested by the Watercooler members on how to onboard a new hire, I outlined what a solid first project would be, along with potential projects for the next 6 months. I also took a first stab at defining what I saw was “success” for her role, with the intention of discussing and riffing on it with her during our first one-on-one meeting later that day.

My personal to-dos for onboarding you successfully – I wanted our new hire to know what I still had yet to do to make sure she was onboarded fully (e.g., making sure she had access to all our software tools, walking her through our back-end administrative system). That way, she’d be looped in the process, and not in the dark about when we’d get to a certain topic.

The exact “Day 1 Welcome Note” I sent our new hire

What’d this end up looking like, all together? Here’s the exact welcome note I sent our most recent new hire, Mandy, our Operations Manager:

Happy first day, Mandy. We are over the moon to have you join us. Today marks the first day of a great adventure together. I’m so honored to get to work with you.

First things first, I wanted to share why we hired you… In the most simple terms: I was impressed while working with you. Ever since we began working together on the podcast, it became obvious to me that you produce excellent work. We highly value the ability to just execute, and I noticed your ability to do that immediately. You have a keen eye for detail (so important in your role!), adjusting things based on feedback – and you very quickly grasped our brand. Those are not easy things to do, so that really stood out to me. You also receive feedback wonderfully: Openly, objectively, and non-defensively. In fact, you communicate in a very level, clear way, which Daniel and I also highly value. And, in all our conversations, you exhibit incredible perseverance and rigor. I see a builder in you: You’ve built something awesome with DevReps – and I know the potential for you to build even more is 100% there. And so, I jumped at the chance to bring you on full-time! And now, we’re here – and I feel lucky. Working with someone of your caliber is what makes building KYT a meaningful journey for me, personally.

Alrighty, let’s get to the good stuff – getting you all situated in KYT! To give you full business context, I’ve added you to all our Basecamp Projects. I recommend going through each one – reading some of the messages, poking around in the documents to get a sense of everything. In particular, here are some documents to give you the most context of the business:

  • KYT History [LINK]
  • KYT Purpose, Vision, Values [LINK]
  • How We Work [LINK] KYT Business Context [LINK] Key Milestones [LINK]

I definitely don’t expect you to absorb it all in a day – let alone in a single week (or even a month!). It takes a while to feel really comfortable with our brand, business problem, audience, etc.

I’d also love to get a sense of your work style + preferences. When you get a moment, could you fill out this little questionnaire here? [LINK] Once you respond, I’ll share mine and Daniel’s answers too.

I also took the liberty of a first stab at potential objectives + projects for our first 6 months of working together (see below). This is 100% a draft that needs your input, heavily, so let’s discuss during our call later today. [LINK]

For reference, here’s a little to-do list for me of some of the more tactical stuff we need to cover + knock out during your onboarding. [LINK]

Last thing I want to mention: We want your fresh eyes. If there’s something you notice that’s weird, or you wonder why we do it that way – please tell us. It’s just been the two of us for the past two years, and so there’s likely many things that seem strange or things that can be a ton better. Your observations on those things will be so helpful.

Whew! Okay, I think that’s it for now. Please let me know what questions you have. Take your time going through it all – so looking forward to chatting later today. And, again, welcome!

I’m sure as we hire more folks, this process will change – and I look forward to getting feedback from Mandy herself, one of our new hires, on what she thought could’ve been better. Though, you’ll notice: There’s an emphasis on mentorship, on documentation, and on providing as much context as possible.

In the meantime, I hope pulling back the curtain how I’ve thought about how to onboard a new hire is helpful for you in thinking about your employee onboarding process in a remote team.


  • Have mentorship or a buddy system – 51% of remote managers said they have a mentorship program or “buddy system.”
  • Consider partially onboarding the person in-person.
  • Hold weekly one-on-ones for at least the first month.
  • Nail the basics – share institutional knowledge, communication processes, etc. from Day 1.
  • Have a clear first project for your new hire to execute on.

Put this into practice with Know Your Team:

  • Kick off our Icebreaker feature to support your onboarding process – it asks five fun questions every time you add someone new to Know Your Team.