Leveling Up with Design Games: a multiplayer approach to design mentoring

Dylan Häs
DocuSign Product Experience
9 min readJun 29, 2021

The highly structured approach of traditional one-on-one design mentoring doesn’t work for every-one. In this article, I discuss finding an alternative approach at DocuSign that scales from one to everyone.

Graphic illustration of board game “Guess Who” but instead of people faces it has font faces. Illustration by Dylan Häs.

Guess who’s mentoring?
How I got here in the first place

My first design job was an old-school agency gig where hierarchy and titles directed the creative process. As junior designers, we would receive an outline from our Creative Director and fill in the blanks…but if we tried colouring outside the lines (or even suggest another concept) it was an invitation for critique that sent many of my colleagues home in tears. Design fundamentals were run like drills, while pitch sessions felt like hardball.

Although I’m grateful for the experience, I’m happy that style of agency is largely a thing of the past. As I transitioned from print to web, hierarchy was flattened, paving the way for everyone to share their ideas and perspectives. Nevertheless, it seemed design mentoring still followed a highly structured approach that emphasized hierarchy. Worse yet, the higher-up your mentor, the less accessible they became.

These days, I’m in a position where designers are approaching me for mentoring. It’s incredibly flattering, but I don’t subscribe to the dogma of my predecessors. I am the perpetual student — always learning — and it was this ethos that inspired me to find a more egalitarian approach to mentoring…but, also (perhaps selfishly) because I love to learn.

As I worked with my mentees, their needs shaped the rules for a new way of mentoring:

  • Mentoring needs to feel safe: Besides being demoralizing, poorly formed critique can silence designers who are just starting to find their voice. I needed to foster a safe environment where designers can feel comfortable creating without fear of critical remarks.
  • Mentoring needs to cover fundamentals: As our industry has matured, we’re seeing UX designers who are well versed in the nuances of information architecture, but otherwise unfamiliar with design fundamentals like colour theory or typography. I would need to cover design fundamentals in a timely and contextual way without resorting to lecturing.
  • Mentoring needs to be fun: Whatever we do, it needs to be fun. It can be challenging to motivate designers to hone their craft when it’s not tied to a tangible reward like compensation or career progression. Instead, we can borrow ideas from game theory to produce challenges that meet designers at their skill level while rewarding them with a flow state.
A graphic illustration of a roulette wheel, dice, and game chips, except instead of numbers on the roulette wheel or dice, we have various design iconography. Illustration by Dylan Häs.

A roll of the dice:
Can we adapt alternative approaches to mentoring for design?

UX design is a relatively new field, but the challenges we’ve encountered have often been solved elsewhere. Approaching it like a design problem, I wondered if we could learn from how other professions approach mentoring — athletes practice rigorously before a competition, musicians warmup before a concert, actors exercise with theater games before a performance — could designers do design games to improve in a similar way?

One of the nice things about working at DocuSign is our guild programme, which allows members of the design team to work on ancillary initiatives outside the scope of their usual work. This is where I tested my design games approach to mentoring, with a simple game of “coworker caricatures.” After a demoralizingly tepid response, I tried incentivizing it by screen printing drawings, and later gamifying it as a collectable trading card game…alas, no dice.

Designers saw the challenge as extra work that wouldn’t return any value, others felt the challenge was too great and this prompted anxiety, and a few designers were bored by the lack of challenge.

This was great feedback. Anxiety, apathy, and boredom are signs that there is a mismatch in the perceived challenge level and the designer’s apparent skill level. We can move to a more positive state (and potentially flow) by adapting the challenge to the skill level.

Nevertheless, even after making the challenge adaptable, designers saw these games as superfluous extra work. There was a bigger issue here: we needed to cultivate a culture of creation.

Graphic illustration of various team sports objects surrounding a play button. Illustration by Dylan Häs.

Mentoring is a team sport:
How we cultivated a culture of creation

In 2019, I started a new design game called “Dance Party.” Every Friday, I would spend a few minutes designing a dance party poster and ask our org to respond with music they were listening to that week. The response has been tremendous. Members from across the org look forward to our weekly dance party; it’s an opportunity to connect in our highly distributed team while sharing something deeply personal: music.

A year (and 52 posters) later, the dance party had become ingrained in our org culture and we started seeing more designers sign up to play this design game. Designers who play see their work broadcast to the entire org, and recently we’ve started reposting these posters to our team’s social media.

“LOVED this design game! I learned a ton and really enjoyed getting to know my colleagues through this challenge. I really loved the level of support and encouragement everybody showed — it was a really cool thing to witness.”

Anecdotally, participating designers have shared that it’s been a fun way to “practice their design chops,” others have used it to “learn about Bauhaus and the golden ratio,” and overall it’s been a way for designers to explore design outside their usual assignments.

With this supportive culture in place, design games started to take off. We’ve had some misses, but our biggest hits have been with Internal, External, and Collaborative Design Games.

Selection of posters from our weekly design game, “Dance Party.”

Internal Design Games

The weekly “Dance Party” game (see some of our posters above) is an example of an internal design game. Internal design games depend on a strong culture and (in our case) can take over a year to get rolling. We experimented with the format a lot, but what worked best for us was (1) having a clear brief, (2) a regular cadence, and (3) using a subject that we can all appreciate (like music). Check out the brief for our most successful design game, see if it works for you, and try remixing it for your team.

Other internal design games your team can try:

Selection of lettering from our recent #36daysoftype challenge

External Design Games

The greater design community has a wealth of design games and challenges. We’ve had a few of our designers take on the #dailyuichallenge, but open challenges like this can be overwhelming or intimidating. Instead, we’ve found success tackling challenges as a group.

Recently, we completed the #36daysoftype challenge (see some of our lettering above), where each day we would work on a single letterform together. By working on an external design game together, we’re able to hold each other accountable, while mitigating the overwhelming scale of an external challenge.

External design games your team can try:

Coming soon: Figma Tennis

Collaborative Design Games

Unlike the internal/external design game examples I shared where designers work solo, collaborative design games are for creating together. We’ve had some success doing an exquisite corpse exercise during our last offsite, but we wanted to curate a more intentional approach with predictable outcomes.

To do that, we are playing a new design game called “Figma Tennis.” This was inspired by Coudal Partners’ Layer Tennis, where players would take 15-minute turns remixing a shared piece over the course of an hour.

In our version of Layer Tennis, designers tag-team a brief before an audience of their peers. Figma’s multiplayer technology allows us to serve the game as an exercise in pair-design. Stay tuned for a dedicated post about our Figma Tennis matches.

In the meantime, here are some collaborative design games your team can try:

Leveling Up:
Top 3 things I learned from playing design games

Design games are a lot of fun, and unexpectedly a great way to multiply your mentoring efforts. I’ve been workshopping the approach for almost two years, here are the top three things I’ve learned in that time:

1. Keep it brief.
A clear and concise design brief helps designers focus on the challenge, while the regular cadence creates momentum. See how we did it with the weekly Dance Party design game.

2. Incentives help.
We saw spikes in designers signing up to play when we received shoutouts from leadership and when we started promoting the dance party posters on our social media.

3. Highlight what works.
Although it is tempting to offer spot feedback on work generated in design games, we’ve found that discourages play. We have a simple rule that feedback needs to be invited, which helps create a supportive and fun environment for creating.

Instead, try pointing out what works. Everyone has something to teach and it’s our job as facilitators of design games to highlight these lessons hidden in the work of designers.

Example: during the #36daysoftype challenge, I dedicated parts of my series to participating designers. I would post a detailed analysis of their work, pointing out design fundamentals, motifs, and techniques, which I could then turn around as fan art. This helped teach by example and motivate with the promise of fan art.

Please keep in mind that while design games are a playful addition to the mentorship toolkit they are not a replacement for one-on-one mentoring. One-on-one design mentoring will be more appropriate when teaching soft skills, or if your design culture is not receptive to collaborative play. This is something for you and your designers to learn on the field.

Game on:
Feedback from designers who came to play

It can be hard to measure the success of mentoring, but this gamified approach returned a lot of anecdotal evidence for my mentees and I. Here are some of the messages I’ve received from the designers I get to work with:

  • Honestly, I feel like this project helped me do “the work of my life”. I’ve been in a creative rut for a while, and this project helped me diagnose why. The discipline of this focused daily visual work pushed me out of my rut and helped me build a new confidence that I can bring to my DocuSign work as well as any creative work I do to nourish myself. For me, visual art is a form of self care… making it, enjoying it, talking about it, etc all nourishes my life and makes me a happier person. It was really special to get to have that be a bigger part of my daily work for a while, and be reminded that the career I chose for myself is pretty dang cool.
  • I really enjoyed the design game we had — it inspired me to keep going and keep creating even if I wasn’t satisfied with my work. Overall, had a really fun time with this challenge! This is the first time I’ve completed a design/art challenge!
  • LOVED this design game! I learned a ton and really enjoyed getting to know my colleagues through this challenge. I really loved the level of support and encouragement everybody showed — it was a really cool thing to witness.
  • I really enjoyed when people would share how they made things. Those were the tips I was looking for and hoping to get out of this challenge.
  • I learned a lot of new techniques using Procreate, I also learned what styles I am drawn to, and I feel like I learned more about my coworkers through their art expression.

Ready to play?
We’re looking for a few good sports

How do you mentor to the masses? Let us know below in the comments or through our design and research team’s instagram.

Ready to get off the bench? Come play design games with us at DocuSign by checking out our latest openings here.

Illustration credit: Dylan Häs

--

--