Modeling Mentorship

Mentorship is a common topic of conversation in our industry, but the word “mentor” is rarely discussed or expanded upon. This leaves a lot of people — especially young designers and developers — without a clear path to finding help. Mentorship comes up frequently in the Spec Slack team, on Immutable, on Design Details, and I just recently recorded a conversation at Epicurrence that delved into the topic. The frequency of these discussions has led me to the realization that our modeling for what mentorship means is due for an overhaul.

After I dropped out of college in 2008, I worked as an engineering assistant at a local recording studio for a couple of engineers whose work I adored. They spent their days filming indie documentaries about bands I loved and recording live albums for artists like The Pixies. In between fixing up old Mac Pros and setting up microphones in the studio, I would end up doing a lot of “design out of necessity”. I didn’t want to be a designer, I just did things because they needed to be done and I happened to have a pirated copy of Photoshop lying around.

I was more-or-less an apprentice and mentorship was the primary purpose of my time at the studio. While I’m sure I grew from working there, I’m skeptical that I learned much from the engineers directly. I looked up to them so much that I never questioned their advice. They never asked me to figure things out or approach a problem differently, they just gave me a solution without explaining how to get there. Looking back, I see that this was a perfect lesson in how not to mentor others.

Mentorship as a concept

Books and movies portray a mentor figure as a sage advisor, often a mysterious paternal character who imbues their protégé with mystical insight or profound knowledge. Since we already have a huge Imposter Syndrome issue in our industry, thinking about mentorship based on this model just keeps people from providing assistance to others simply because they feel either inadequate or not “wise” enough.

Advice doesn’t need to be deeply meaningful or supernaturally prescient. It just needs to be pragmatic. It has to be actionable. All of the best designers and developers I know learned through immediately putting things they learn into practice and repeating it over and over — not by reading a book, pulling a Neo “I know Kung-fu”, and suddenly being a developer. It’s about practice, not encyclopedic knowledge.


Merriam-Webster defines mentor as “a trusted counselor or guide”. It says nothing of Doc Brown-ish eccentric brilliance or Yoda-esque expertise acquired over a massive amount of time. There are only two factors at play in that definition:

  1. Are they a person?
  2. Do you trust them?

It has been pointed out to me that there isn’t just one kind of mentorship, either; it isn’t defined by the traditional 1:1 archetype. After examining the sources of valuable advice and growth in my life, I’ve come up with 3 primary mentorship models:

1. Direct Mentorship

This is the easy one: the most commonly-portrayed mentor model. Examples include Parent:Child, Master:Apprentice, Teacher:Student, Miyagi:Daniel-San, Ben Kenobi:Luke Skywalker, and Paul Newman:Tom Cruise.

This type of mentorship is built upon a pairing of two people: one experienced and one inexperienced.

While there is nothing inherently wrong with this model, it is certainly the least efficient distribution of information. It’s insular by definition and suffers from a lack of perspective. You can’t learn everything from one person and what that person has learned won’t always apply to you. Also, the power in the relationship is generally held by the mentor which can discourage valuable debate.

With that said, some of the most valuable advice I’ve received has come from 1:1 conversations with people I trust. On Immutable, when asked about seeking out mentors, I mentioned Brian Lovin as someone I consider a mentor. He’s younger than me by a few years (so I can’t check off the elderly box) and, while I’d say he’s not necessarily more broadly experienced, I do think that he has experience — and more importantly, different experience — in key places that I’d like to learn more about. Nothing arcane or unknowable without his help, but having quick access to that experience when I’m working on a similar project is invaluable.

I’ve also gotten chances to mentor others 1:1 through our Slack team. It’s fairly common for someone to DM me and ask for advice on a project or applying for a potential job. I’ve only been in this industry for about six years and only active in the community for three, so I’m by no means an expert, but I’ll offer what experience I have to try and give them whatever boost I can.

2. Broad Mentorship

This is the most commonly underestimated form of mentorship in my experience and it generally consists of a person or group of people trying to share their experience with others as broadly as possible. Examples include Speaker:Audience, Author:Readership, Yoda:Younglings, and Ms. Frizzle:3rd Graders.

Seat belts, everyone!

One benefit of broad mentorship is that a 1:many relationship encourages a more open conversation and allows for a stronger, more diverse, multi-faceted debate than 1:1 mentorship does. It also enables a wide variety of distribution methods making it more efficient than 1:1 mentoring by its very nature. I believe that blog posts, podcasts, public Slack teams, and occasionally even Twitter are some of the best channels for mentorship for our generation. Being open and honest about everything you can with as many people as you can is a good way to help others without really costing anything. Some examples of this distribution that have made a huge difference for me personally are:

When Brian and I started Design Details, we said that we were trying to meet our favorite designers. Looking back, I think that we were actually seeking out mentorship for ourselves. Thankfully, due to the format, we were able to share it on a wider scale without creating more work for the mentor. Because of this, we’ve both learned a great deal in a short time and we’re now commonly approached by others for advice, help, and critique.

Which brings me to my third category…

3. Critique

Critique is a many:1 model with a focus on a single person or group’s work. It’s hard to get this mentorship model right as it depends on a high percentage of people involved having a voice and relies on significant investment and understanding from both parties. The person being critiqued needs to know how to frame the problem and how to turn raw feedback into a better outcome. On the other hand, the critics must try to provide useful, pragmatic, constructive feedback which encourages iteration and pushes people to consider a given problem differently. Not better, just differently.

Dustin Senos once shared with me a very thoughtful way of handling this that he used when he led design at Medium. Each person would get a chance to present their work and during this time, they would be the only person allowed to speak. When they were finished presenting, each person at the table would get a turn to present their list of pros/cons — thus giving each person at the table their own allotted time and enabling the quieter voices to be heard equally.

In our Slack team, we have a channel called #Inspect that has a feed from our Wake account where people can post their work and receive critique from others on the team. Every week, we have an event where we bring in a prominent designer to help critique and guide the overall process. The format of Wake allows people to give feedback in their own time, communicate back and forth with the designer, and everyone has a voice without interrupting others. Wake is also invite-only which prevents the channel from getting too noisy or becoming destructive.

One of the best advantages that designers have is their ability to learn to give and take constructive criticism. No other industry I know of puts such a heavy focus on the value of critique and it pays dividends once you learn to take it well. The clearest sign of a truly great designer is how constructively they format their critique and how well they take feedback from others.


Looking for a mentor?

Go follow people you look up to on the internet! Twitter and Medium are easy places to begin (Here’s a good Twitter list to get you started!). Engage in conversation when someone mentions something you want to know about. It’s ok to ask questions! Want more frequent long-form discussions or advice? Subscribe to some podcasts that feature people you want to know more about. Want a deeper conversation? Go join a Slack team that has more experienced people from your industry (I‘ve heard there’s even one that features public critique 😉). There are easy ways to get engaged and that doesn’t mean you need to go around looking for a wizened old hermit.

Want an easy way to start mentoring?

Go share what you know with others! That’s all it takes. No matter how “junior” you are, you always have something worth sharing. The people you share with might even share back and then everyone wins! It’s easy to offer advice to younger designers, but helping designers you look up to — even with simple things — is just such a wonderful feeling and I couldn’t recommend it more.

Now, go get involved! If I can encourage more designers to help each other, that’s all I can hope for. I’ve been fortunate to have the opportunity to meet many of my heroes in the past year or so, but some of the most valuable advice and discussion has come from people that tend to fly under the radar. People who many times don’t think of themselves as “the mentor type” have helped me grow immeasurably.

Each generation of our industry stands on the shoulders of giants and we have all received critique, encouragement, and knowledge, directly and indirectly.

Don’t be nervous to ask, don’t be afraid to share.


Thank you to Adam Morse, Marc Edwards, Sarah Marie, Kris Puckett, Brian Lovin, Dan Mall, Andy Bromberg, and especially Dustin Senos for helping me process these thoughts.