The very first one-on-one

Setting up your new design hire for success

New jobs are exciting, hopeful, and a little nerve-wracking. Set a positive and safe tone in the very first one-on-one with your new designer. You are the guide through their first time user-experience at this new job.


Start the conversation by briefly describing what the one-on-ones are for and how your designer should rely on you. For example:

This meeting is our regular time to checkin on how you’re doing. It’s a way for me to learn how I can support and unblock you. It’s not my job to specifically check up on your project work but we’ll probably talk about it often. Let’s use this time to reflect on your experiences in the company, industry, and whatever else is on your mind. You own your design career but I’m here to help you find success and happiness in your work. How has your first day been?


Your designer should be doing most of the talking. Invite comfortable pauses for them to gather their thoughts and digest your comments. Use your user research skills to follow their lead in the conversation but guided by your intentions.


This is your time to learn who your designer is and what they care about. Save any housekeeping topics or task items for the end of the session. This will implicitly communicate that the one-on-one is their time. And it is.

Ask what they’re most excited about or hoping to learn. Your designer’s last job is more fresh in their mind than it ever will be. What did they really appreciate about their last manager? Was there something they needed and never got? Remember their past experiences are historical data, not your competition. There is a reason they changed jobs.


One-on-ones can seem like an expensive investment to the company’s bookkeepers. But, people quit managers not jobs. Regular one-on-ones improve retention. There are so many wonderful design jobs right now. It’s more expensive to recruit and onboard than it is to take 30–60 minutes every week.

One-on-ones are also a direct-line to the health of people who are building the products and services that fuel the business. It’s also your job as a design leader to report upwards when you anticipate problems within the people and projects. The time you take to support the people on your team supports the overall mission of your company.


Setup time for a one-on-one for their first day of work. Only you and your new designer should be in this meeting.

Decide what kind of tone and boundaries you want to set in the conversation and choose an environment to match. Meeting at mid-afternoon or the end of the day in a private and comfortable space makes for a good time to reflect, answer their questions, and have a calm and nurturing conversation. Avoid windowless conference rooms, extreme temperatures, strong smells, or loud spaces where you’re likely to get interrupted and distracted.

Save your onboarding decks, process instructions, and skills assessments for sometime outside the very first one-on-one. You can still expect HR and system questions during the first few weeks anyway.

Hand painted welcome letters


Designers are usually moved by visual details. A small gift of relevant office supplies and a hand-written welcome letter on beautiful stationary goes a long way. It can subtly communicate you’ve been waiting for their arrival and their presence and work in the company is valued. It can also show that even in a technical environment aesthetics and beautiful experiences matter.

There are no universal rules in design and leadership. Adjust these practices for the individual, the context, and your personal management style.

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