My experience as a design mentor

October 1, 2019

This year, I had the opportunity to be one of Stack Overflow’s first design mentors for Phoebe Leung, one of our new hires this year. I love the people part of my job and dove headfirst into this opportunity.

A good mentor is someone whom the mentee would describe as “X helped me in my career.” - Julie Zhuo

I’d never been a mentor in a formal sense, so I researched what a good mentor-mentee relationship looks like ahead of time. I learned a ton through folks like Julie Zhou (her book), Lara Hogan (her book), Michael Lopp (his book), and Cap Watkins.

It would be near impossible to summarize everything I soaked up, but I noticed a few themes in my research. I learned that a good mentor…

…creates a safe space and helps the mentee assimilate into the company and their role.
…helps with skills and career development.
…opens doors for the mentee and helps them make connections.

With Phoebe’s permission, I’d like to share how our experience played out, what tactics I used, and what we learned together.

⚠️ Warning: This article contains a Stranger Things S3 spoiler.

Set up (and prepare for) regular 1:1’s

1:1’s are a great way for mentors and mentees to develop a strong relationship and ensure that mentees are working toward their goals. They’re not status update meetings; they’re an opportunity for a mentee to ask questions, get regular feedback, and grow into the company and their role.

Soon after Phoebe’s first day, we set up regular 1:1’s. In our meetings, I always prioritized her questions (more on that below). However I always prepared other things to talk about, only one of which was project work. Other stuff included private design critiques (both her work and my work), in depth design/research discussions, skills development, team culture and history, and company processes. I thought this was helpful because I was sharing both my expertise and institutional knowledge. Since she may not have known what a mentor can offer, my hope was that made her aware of things to look out for and also give her examples of what types of things she can ask me.

We started with three 30min 1:1’s each week to start. As Phoebe became more comfortable, we adjusted the frequency of our 1:1’s from three times a week to once a week, and finally to ad-hoc.

Spend time answering their questions.

The questions they think are embarrassing. The ones that might seem obvious to seasoned employees. The ones they feel weird about asking the boss. The goal here is to create a safe space where there are no stupid questions and where the mentee feels safe and supported so they can do their best work. Being available to answer questions is especially important in a remote setting since new hires can’t just tap someone on the shoulder when they have a question.

When answering Phoebe’s questions, I’d supplement my answers with an example or link to a wiki article, Google doc, or something she could reference anytime. Here’s a random sampling of questions we went over in our first few weeks:

Who should she meet in her first week?
Why do some designers use Sketch and others use Figma?
What is a branch in Git?
How does the company’s education budget really work?
What is flexbox?
Are all design critiques typically like the one last week?
How do designers typically work with product managers?

With each answer, I used some of my industry and institutional knowledge to make my mentee feel more at home.

As Phoebe became more comfortable, she had fewer questions. When this happened, I started asking questions like “What doesn’t make sense to you at this company?” or “How is your relationship with [team member]” or “What area of the company would you like to learn more about?” My goal here was to help her form good relationships with her team and feel like she could speak up and ask questions as a new employee.

Our chats weren’t all about business. Phoebe also helped me through a running injury I had over the summer and we brainstormed ways that Jim Hopper could still be alive at the end of season 3 (mark my words: he’s alive in The Upside Down!). Making time for personal conversations also helps build rapport and camaraderie.

Ask them what they want in their career and ask what you can do to help.

As a mentee becomes settled in their role, conversations can become less tactical and more strategic. Asking questions like “What would you like to be better at?” and “Where do you want to be in two years?” It’s important to listen for their aspiration, keep it in mind, and keep an eye out for opportunities.

Phoebe wanted to improve her front-end skills, so we created a learning plan that looked something like this:

Complete SuperHi’s Foundational HTML/CSS/JS course (she was already doing this on her own).
Learn the box-model concepts.
Learn flexbox.
Build a landing page in HTML and CSS.
Rebuild said landing page using our design system.
[stretch goal] Contribute something to our design system.
[stretch goal] Keep a journal throughout the process so we can write a blog post at the end.

To keep ourselves accountable, we assigned a deadline to each milestone. As we reviewed her progress, I asked her questions about her code and tried to push her a little bit out of her comfort zone each time.

“This layout looks great on desktop, how would you adapt it on mobile? … Now might be a good time to talk about responsive design. Are you familiar with media queries?”

We fell behind schedule a few times when project work took priority over self-development time (we all know how that goes). But Phoebe was quick to absorb everything and apply it to her learning plan. I consider her a capable front-end developer. 💪

Sponsorship and opening doors.

On the topic of stretch goals, another thing mentors can do is think about the different opportunities you have to offer up a mentee’s name in situations that can lead to even more growth and opportunities.

Sponsorship is all about feeling on the hook for getting someone to the next level. As someone’s sponsor, you’ll put their name in the ring for opportunities that will get them the experience and visibility necessary to grow in their role and at the organization. - Lara Hogan

That means…

…giving them visible/public recognition in the company.
…suggesting stretch tasks that are just beyond their current skill set. Tasks that help them grow, take on more complex projects, and get a future promotion.
…opening doors for them to develop a relationship with another person, start a side project, give a company presentation, write a blog post, etc.
…keeping your mentee and their aspirations in the back of your mind, so that when you come across something that might be useful to that person, you can share it with them.

Phoebe and I would often review her both her project work and her self-development work. I shouted her out in our design team meetings, to her PMs and managers, the company’s “kudos” doc (a weekly email of praise and thanks, sent to ~50% of the company), and generally to anyone she works closely with.

After a few months, I could see that Phoebe was settling into her role, so I looked for opportunities to push her out of her comfort zone a little. I created a good “first GitHub issue” for her to learn our GitHub workflow, helped her craft her performance review pitch (which our titles and compensation are based on), and pushed her to write a blog post about her experience joining Stack Overflow. After six months, I’m still keeping an eye out for growth and sponsorship opportunities.

It’s important to strike a good balance between mentoring and sponsoring. Lara Hogan reminds mentors not to over-mentor, but under-sponsor mentees. Ultimately the goal of a mentor is to help the mentee get to the next level; offering advice is only part of the equation.

Wrapping Up

As mentors, we want our mentees to reach beyond us, because our mentees’ success is ultimately our success. - Lara Hogan

I truly believe this. I’m incredibly excited to see Phoebe tackle a new problem and come up with a creative solution on her own.

Mentorship relationships evolve over time because each party is growing, so it’s an ongoing process. I’m super thankful that Stack Overflow gives individual contributors the opportunity for things like mentoring. It’s been a highlight of my career.

Be sure to read Phoebe’s take on our experience too! ✌️

Also published at https://medium.com/@tedgoas/my-experience-as-a-design-mentor-c463942a063b