Why Onboarding Matters — 4 Ways to Redesign New Hire Success

Kelsey Peterson
The Culture People
Published in
8 min readMar 8, 2021

Welcome to 2021 — where businesses are competing for global talent and onboarding is top of mind to avoid burnout and costly turnover. Are you keeping up?

Photo by Gelatin from Pexels

In nearly 11 years, I’ve gone through onboarding for 10 different jobs. On average, that’s 1.1 jobs per year. Considering how long onboarding can last (anywhere from 1–7 months), this means I’ve spent years learning about benefits, healthcare, values, business goals, and culture, at the same time as getting started in my new role. I’ve spent 88% of my career as an employee and now lean on those experiences to design recruiting, onboarding, benefits, and HR operations for — well — people.

Every onboarding experience does one thing — it teaches you what is expected, how you conduct yourself at work, and what the culture will be like. At least it should. Instead, I mostly learned what I shouldn’t do through actions I witnessed during onboarding:

  • Unless I’m in leadership, my ideas don’t matter
  • I can only take short breaks or else I won’t be paid
  • Even when I’m asked for feedback, I can’t be completely honest
  • While curiosity is a value, I shouldn’t ask too many questions

An employee handbook, policy documents, and what’s presented on the website is one thing, but actions speak far louder than words. We all tell ourselves stories when conflicting information is presented.

However, out of the ten onboarding experiences I’ve gone through, I’ve only seen one built with intention. On your first day at Square Root — an award-winning startup — we’d cover everything you need to know in 20 slides (with cat GIFs), get to know each other personally, you’d only receive two, simple emails from the People team, and we’d personally take you to lunch — either in-person or virtually with a digital gift card.

Experience is everything.

Some fun facts from Work Institute’s 2020 Retention Report:

  • 77% of new hires in the first year are open to new opportunities, and 44% of those are actively looking for new employment
  • 78% of employee turnover is preventable by employers — the top 3 reasons for leaving a job in the first 30 days are job characteristics, work-life balance, and well-being
  • Turnover due to work-life balance has increased by 22% since 2013 — a sub-reason in this category, Commuting, has increased by 334% since 2010 (another reason for Work from Home/Anywhere policies)
  • Turnover compromises growth and profit — the total cost of voluntary turnover exceeded $630 billion in 2019. Turnover costs roughly 6–8 months of that departing individual’s salary.

So, why take the gamble? Why not create an enriching employee onboarding experience? Why not set them up for success on day one?

If you’re curious how we helped our new folks be successful, impactful, and feel connected in a virtual world, keep reading. If you think this could help anyone else, feel free to share and spread the love 💜

Send benefit docs and all paperwork before they start.

Once you receive their executed offer letter, NDA or PIA, and completed background check, save them some of the headaches of starting a new job by sending all benefit docs and paperwork before their 1st day.

We house these documents in a shared Google Drive folder that gets regularly updated. New Radicals can look them over ahead of time, ask questions via email or phone, or wait until after they start. This gives them the choice to read through our documentation when it works best for them.

Haven’t you ever had too much information thrown at you on your first day? Empathy helps to create a magical experience — when in doubt, ask them what they’d prefer!

Lead by example.

Do you expect your new employee(s) to work past 5 pm every day? If so, why? Do you want them to provide feedback, be curious, and ask questions? Do they know what’s expected of them? Are they encouraged to take plenty of time off, decline meetings that conflict with their life, and debate for better solutions? Our motto: don’t be a hedgehog.

The hiring manager, the team, and people + culture set the stage during the first month. Watch what you encourage with your actions and what you say (or don’t say).

In former onboarding experiences, I’ve been told:

  • “We never get anything done on time here, so if you can’t have this done by X, it’s no biggie”
  • “Sometimes you might get some weird and inappropriate customers. If that happens, just walk away”
  • “The CEO might ask you to help with a project randomly in the hallway. If he does, always say ‘yes’ no matter what”
  • “If you need to take a bathroom break, it can only last for 5 minutes. I got you a whiteboard, make sure you always write down where you go”

Unfortunately, many of these come from companies that have inspiring values and a strong vision for their culture. But if those values are not operationalized, they’re just words.

This is how I learned that my time isn’t important, I should just ignore inappropriate situations, I have to be available 24/7, and that I shouldn’t try to reach a deadline.

It’s crucial that you put your values into action, especially for new employees. Taking one of the stats from the beginning — if 77% of new employees are open to new opportunities, and they find out that their new employer doesn’t truly support their time or perspective, they are going to leave.

Recruiting is getting them in the room; onboarding is empowering them to stay.

Communicate expectations in one place.

In 2020, I created a Google doc for each virtual new hire, a one-stop-shop for everything they need to know during the first month. This included:

  • Intro + Welcome — why we created this doc and encouraged them to give feedback on how we can make this process better for future hires. Feedback is provided to the hiring manager or people ops. Either way, we want them to feel part of the creation and success! Pro tip: take action on the feedback or update them on the status.
  • Assignments — even if this isn’t carved out until a later week, we mention that it’s at least coming and when to expect it to be added. Once their assignments are established (i.e. which customers they’re supporting if in a customer-facing role), I add in the information so it’s all in one place.
  • Recurring Team Meetings — all weekly, bi-monthly, and monthly meetings that take place on their given team (i.e. Engineering or Operations). They’re still invited to the meetings on their calendar, but having it in a doc allows for additional context: why the meeting exists, how it came to be, and what they can expect.
  • Recurring Company Meetings — includes our all-hands meeting every Friday to share “happy news,” announcements, and present important information; weekly kick-off every Monday; bi-annual Hackathons; annual sensitivity and goal-setting workshops. Listing these regular occurrences reinstates the vibes of our culture — with sensitivity training, we care about treating each other with respect and being an inclusive environment for everyone; with Hackathons, we value curiosity, innovation, and experimentation.
  • What to expect during your ___ week — I break this up into four sections: 1st, 2nd, 3rd, and 4th weeks. By bringing the entire team together, we can craft a full story of what they should know by the end of each week. For instance, by the 3rd week, we want each new hire to have an idea of how they’d like to use their Learn Anything budget.
  • Lastly, the full orientation schedule — new hires are still invited to each session via their calendar, but listing it out here allows for me, the hiring manager, and the team to understand the full picture of their schedule. Too many meetings mean not enough time to absorb new information.

Gather Feedback, Reflect + Repeat

When I joined Square Root in mid-2019 and started conducting all 30-day check-ins, I didn’t just listen to feedback — I kept a record of it. I also didn’t use a survey; I met with each new hire and we discussed their insights together. There’s nothing more refreshing than seeing (or hearing) onboarding from fresh eyes. Some of the questions we ask:

  • What has helped? What would you have liked more of?
  • Is the role meeting your expectations? What could we have done differently?
  • How is your relationship with your manager?
  • Favorite part of your role? Least favorite?
  • How could the culture + people team do better? (culture = our product)

Once you gather feedback, reflect on it! Put yourself in their shoes and consider new ways to redesign the experience for the next new hire.

Consider how onboarding feels and the themes you see in the feedback — are there too many meetings? would it be helpful for them to have a buddy? were expectations not correctly stated during recruiting + the offer?

We’re a product of our experiences so I’m going to tap into my educational background for a minute — we all learn differently.

Some people might love the fine print and go through it on their own; others might need to be guided or see it shown visually. I’ve personally struggled with a learning disability all of my life, and I sometimes have to read a sentence over and over and over again (often while saying it out loud for myself) to fully understand what it means.

I leaned on this experience when previously training + teaching customers how to use FinTech software. The result? Folks ended up asking to train with me specifically because I created a unique experience for them. During the recruiting process, this is why we ask “how do you best learn?” That simple, easy question shows that you care.

Adapting to the new world of remote onboarding allowed me to lean into the Why? for Square Root’s onboarding process. This process had to change — and for the better! I couldn’t rely on seeing each individual in the office anymore, next to our Bevi machine (the “watercooler”), or at a weekly happy hour.

Instead, we need to create the spaces to ensure each new person is welcomed, understands expectations + deliverables, and feels psychologically safe in our culture.

I’m grateful to be part of an incredible, global HR network — Resources for Humans, created by Lattice. One topic that got introduced last week in Slack was how to redesign a more intentional, kind, and supportive onboarding experience for remote folks. I jumped in to offer how I reimagined Square Root’s virtual onboarding process, and I’m thrilled at how much it helped folks design a program that works best for their organization. Thank you to everyone who inspired me to turn my onboarding structure into an article!

Not only do I manage HR and Recruiting in tech, but I’m also a songwriter, musician, creative coach, and entrepreneur! Learn more about my background via previous articles I’ve written:

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Kelsey Peterson
The Culture People

People + Culture leader ~~ Singer-Songwriter ~~ cat mom