How to onboard a new hire remotely

Recently I hired someone new here at Know Your Team. Here’s exactly what I wrote on Day 1 and the 23 questions I asked as a part of our employee onboarding process as a remote company.

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, remote, 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 remotely.

After all, the numbers on how likely it is for a new employee to leave within the first 90 days are astounding: 30% employees leave before their first 3 months are up, according to a survey with 1,500 people.

It got me reflecting deeply… How to onboard a new hire, and make sure that person feels welcomed, encouraged, and well-equipped to contribute to the team?

From the insights of 1,000+ managers in our online leadership community, The Watercooler, I noticed clear commonalities for what leaders view as best practices for how to onboard a new hire – especially when remote. 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). One company mentioned how the new hire sits right next to their mentor in the office. In a remote team, though, this can happen by pairing folks to chat via a biweekly Zoom call.
Weekly one-on-ones — During the first month, the new hire has weekly one-on-ones with the lead/mentor (and a couple with the CEO as well). After the first month, the one-on-ones slow down to a more moderate pace such as biweekly or once a month. (You can read my piece on the best questions to ask during your first one-on-one meeting with a new hire here.)
Nailing the basics — Many companies have a document that explains processes and details like getting their computer all configured. Other companies set up the new person’s desk with welcome notes, headphones, etc. and/or have an office seating chart with everybody’s name so they know who is who. (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 project-wise. 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

Given the consensus around these recommendations on how to onboard a new hire, I incorporated these elements into our own remote 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 are, too. And so I wrote up a survey with 23 questions:

Where on the spectrum of an extrovert to 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 workday?
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, altogether? Here’s the exact welcome note I sent our most recent new hire, Mandy, our Operations Manager:

☀️ Welcome to KYT, Mandy!
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, our newest hire, on what she thought could’ve been better.

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

👋 Oh hello! You’re wondering if you can automate any of this stuff for your own team, eh? Well, you’re in luck 😉Our Icebreakers Tool in Know Your Team helps you onboard new hires by asking 5 fun, non-cheesy icebreaker questions. It’s a simple way to make sure you never forget to welcome a new hire. Give it a whirl and use Icebreakers in Know Your Team today.

Additionally, we are giving away our Guide to Managing Remote Teams – 60+ pages completely for free. Based on data we collected from 297 remote managers and employees, our CEO, Claire Lew, wrote 11 chapters of best practices on how to manage a remote team.