Helpful Questions to ask During Onboarding 1:1's

Onboarding can be difficult - especially remote. My onboarding experience became more meaningful when I started asking these questions during 1:1's.

Onboarding can be difficult. Onboarding remotely can be even more challenging. It's hard to know who to talk to and what to talk about. I recently went through the onboarding process when I joined the design team at Storyblocks. I was encouraged to set up one on ones with the individuals I'd be working closely with regularly. It was a great way to get to know the people I would be collaborating with on a daily basis.

I treated the first few conversations as more general "get to know you" chats. While enjoyable, I left the conversations feeling that I had made a new work friend but didn't have any greater understanding of the organization or how we might be working with each other. I started then asking the questions below and left conversations leaving much more informed and inspired. I also felt that by asking more structured conversation starters I got to know my colleagues better, professionally and personally.

What is the biggest challenge are you facing organizationally?

This question helped me see the cross-sectional challenges individuals and teams were facing outside of my day-to-day role. It also helped me to draw connections and themes across different workstreams and helped me see how I might contribute, either immediately or down the road.

How do you see us interfacing?

This question helps get at assumptions and working styles. Even if you're familiar with a company's team structure, we all hold different assumptions about how often, when, and why individuals should be in communication.

How can I help you?

I've found that asking this question helps uncover colleagues' pain points I didn't even realize they were facing. For example, I learned that our internal deck template desperately needed to be updated. This was a natural task to take on as the result of some brand refresh work a month or so later.

What are you excited about? What drives you here?

Let's face it - not all aspects of the product design process appeal to us. I've found that asking this question helps me understand where my colleagues' strengths lie, in addition to the types of projects that motivate and excite them. This tends to lead to natural areas for collaboration, or learning something about the organization and/or individual.

What are your favorite design tools to use?

This one is designer-specific, but not always. I've learned about a lot of neat collaboration tools and places to get inspired by asking this question. I was inspired to try out FigJam after speaking with one coworker about it.

What was something helpful that you wished you had known when you first started?

I have found this question to be invaluable and have gotten some great advice as a result. Something one coworker said that will always stick with me is, "don't feel like you immediately have to contribute. Just take some time (days, weeks) to let the information sink in and ask questions."

Read any good books lately?

This is just one for fun. I love to read and asking others about books they've read gives you a window into their life - work-related or otherwise. Also the answer "nothing, my kids have taken over my life" is just as valid of an answer and creates empathy for coworkers.

What's your favorite color right now?

Another one that's just for fun, but still provides insight about coworkers' interests. The "right now" bit adds a fun nuance and sheds light on current inspiration. Shoutout to Haroon for this idea and for being the first person in an interview to ask me this question.

Written by

Rebecca Silverstein