Onboarding: Success for New Teammates

I’m focusing this article on how we onboard our design team members. The underlying principles here can be used with any size org or type of department. Adjust any terminology to how it best fits your team.

Brian Barclay
8 min readOct 25, 2018


Onboarding vs Orientation

Most companies I’ve worked for have had very little in terms of onboarding new teammates, whatever the role may be. The terms onboarding and orientation can easily get confused. For example, this is orientation: You come in on day one and meet your HR partner, you’re handed a thousand pages of documents to fill out, you get a list of what NOT to do, some benefits, maybe they have a list of places to get lunch in the area, then you’re ushered out the door to your seat and expected to succeed. While it’s necessary to get that type of info download, it’s doesn’t qualify as onboarding. Pre and post orientation can feel cold, uninspiring, and set a bad a tone so we need to be actively evolving our processes as we hire each new team member.

For anyone of us working on product teams this is ironic since we’re spending so much time researching and executing precise onboarding flows for our customers. All of us likely have full teams dedicated solely to that part of the product. Our business understand the value of it, so why don’t we approach our teammates onboarding with the same tenacity we approach our product?

For success to manifest in anything you do, it takes preparation and practice. We expect this of our new hires, we should expect this of ourselves when it comes to onboarding. It seems pretty obvious that this is one of the most critical elements to an employee’s (and company’s) long-term success.

At Trunk Club, we’re not perfect but we have some best practices that I’d like to share in hopes to help other companies welcome their new employees in the best way possible. These are just suggestions and you should adapt them in any way you see fit.

Getting Started Right: Hiring

First and foremost, our recruiting and hiring process is pretty robust. We spend a good amount of time with potential candidates getting to know who they are both professionally and personally. This sets the right tone before they’re even hired. We have a democratic process when hiring, giving everyone an opportunity to go over pros/cons and what we like about the candidates skills, but most importantly, personality. Skills are a huge part of the job, but skills can be learned — personality is much harder to coach. We want to make sure the candidate would be someone we enjoy spending most of our time with.

Here’s our process:

  • Recruiter gets the right candidates in front of hiring manager or we source candidates on our own
  • Set up 30min call with specific questions, repeated for each candidate, to remove bias from candidate to candidate
  • 30min skype/hangout presentation of a project they’ve worked on to make sure skill level is there
  • Onsite interview: 45min presentation to the core team, 1.5 hour lunch, 3 x 30min breakout sessions with key stakeholders
  • Debrief with the entire team
  • Accept or Reject

Make the New Teammate Feel Welcome Before They Start

One thing I really like about what we do here is before the new hire starts, we send out an email to our Goonies (product & engineering team) letting them know who we hired, a little background on them and their contact information. We encourage the team members to reach out before the new hire starts and introduce themselves, letting them know how excited they are to have them on the team. If they can, they set up a coffee chat prior their first day so when the new hire arrives they have some familiar meet & greets on the books.

  • Get new hires personal email
  • Encourage your org to email and welcome them
  • Set up meet & greet during their first 2 weeks

Good Documentation

My team is extraordinary at documenting our workflows and process, so when new teammates come onboard they have incredibly detailed “how-tos” around all of our tooling. For example, we have paper docs with step by step instructions on how to set up our staging environment, use Postman to push Trunks through their various states, and how to set up GitHub to manage our design kit. Each paper doc has screen shots or gifs of each step you take. Doing this really helps the new designer feel empowered to learn at their own pace and takes some of the pressure off of the onboarding buddy so that they can focus on the most important aspects of onboarding — building relationships.

  • Document as many of your workflows/processes as possible
  • Keep them in a central location where anyone can access them
  • Include these in your welcome package

Make a Checklist

Probably the most essential thing my design team uses is a checklist of all the things a new hire would need to know to be successful. You can take a look at our Designer Onboard Checklist here.


  • Pre-start items to take care of
  • First day goals
  • First week goals
  • First month goals
  • Hardware and software info

Onboarding Buddy

If you looked at our checklist, you will see that we make sure to assign the new hire an “Onboarding Buddy”. This is the teammates new best friend for the foreseeable future. This covers everything from IT, to slack channels, to design kit know-how, to who they would need to know to be set up for success.

Here’s a sample of what we expect from our onboarding buddy:

During the onboarding process, we aim to make our new team members…

  • Feel welcome and excited about their new job!
  • Get acquainted with colleagues who will help them succeed
  • Create a baseline knowledge of pay, benefits, and other resources
  • Get oriented on the business model, history, strategy, and current priorities
  • Learn how we work as a team
  • Start creating impact

Meet & Greet

We’ve found a lot of success when we pre-schedule 30min coffee chats with all key players (from their product team to the executive team) for the first 1–2 weeks after the new team member starts. This is effective because it gives the new hire dedicated time with their core team and stakeholders before they get overwhelmed with all the how-to’s and project work.

HR and IT

We definitely need orientation as it provides you all the context you need to get started on a successful onboard. At Trunk Club we make sure this process is as painless as possible by having the onboarding buddy make a request to the IT team for all equipment, software, slack channels, and any other needs in and around their workspace. When the new hire shows up on day one, we make sure we grab a coffee with them, show them their desk, meet the team (again) then we take them to the orientation where they spend the first 20mins getting their computer setup. There is an IT lead on hand to walk each member through the process and help with any issues. Next, the HR team walks through the most important parts of the company handbook, watch a video or two, then give the opportunity for a QA. By the time your new teammate gets back to their desk, they’re set with every tool they need to get started.

  • Get all equipment ready and software loaded ahead of time
  • Get the new hire logged into to all the software they’ll be using
  • Have IT on hand to advise and troubleshoot
  • HR ready to give a concise overview of most important things to know
  • Leave time for a QA

Planning Their Success

We also layout their 30/60/90 day success path, defining what benchmarks we expect the new hire to hit by the end of those periods. The onboarding buddy is there to facilitate the new teammate for success by overseeing all the process, tooling, and relationships, while the hiring manager (director or team lead, whatever your company has) is there to help oversee and guide the 30/60/90 day plan and make sure that the new teammate is tracking towards their goals. My personal philosophy is that the first 90 days should be getting to know as much as you can about everyone’s job within the company, why they do what they do, and how/why they do it before any new team member starts to suggest changes. I’m a big fan of the book “The First 90 Days”. I highly recommend this book for anyone starting a new job, whether it’s at the executive level down to a jr. designer.

Get Comfortable

On the new hires first day we take them out to a sit down lunch, giving the design team and new teammate an opportunity to relax for a bit. We find that this helps break up what is a pretty intimidating day and gives the designers an opportunity to bond outside of the office, as the office can sometimes seem forced. At the end of the day, we pop up to the Clubhouse for a drink and more time to get to know one another.

  • Make a reservation for the entire core team
  • Pick a spot where you can have a casual conversation
  • Make it far enough from the office to feel private

Cake or Pie?

The last bit of onboarding comes with a small dose of being put on the spot — it builds character. At our bi-monthly Tech All-Hands we announce all the new hires and give them an opportunity to tell everyone what they were doing before they joined Trunk Club and what they’re doing for their new role. Finally, we give them the question: “Which do you prefer, cake or pie?” I don’t know the context of that question or if we collect data on this, as it predates me, but it’s now become a tradition and I enjoy maintaining it.

If you’re wondering what I prefer… neither cake nor pie. I don’t really do sweets. I know..I know…

Trunk Club is hiring Product Designers. If you think you might be a good fit for the team, please reach out.



Brian Barclay

Head of Design & Research at Amazon, based in NYC. In my spare time I’m a Triathlete, Brewery onwer, and Musician.