Helping a growing design team identify areas of personal expertise to encourage better collaboration

The problem

I joined Divvy in March 2021 as the 10th designer. By June, our team had more than doubled in size. With so many new designers, there were some clear cultural gaps and growing pains that our whole team needed to navigate.

One of those growing pains we needed to address was a knowledge gap — we didn’t have a good idea of which members of our team were particularly skilled in which areas. This made it harder to collaborate effectively and get good, timely advice from the right people.

My first 1:1

In my very first one-on-one meeting with our Director, I asked a lot of questions that were roughly “Who on our team is the best at [a given skill or discipline]?”

It was my first time on a design team with more than 2 people, and I was trying to build a sort of mental rolodex of who I should reach out to when I wanted advice or feedback in a specific area. I wanted to know what everyone’s design super powers were, so I could call the right hero at the right time.

Not just a “me” problem

After a couple of months at Divvy, it was clear that we were in the thick of dealing with all kinds of growing pains. What had previously been a small team of (mostly senior) designers was now a healthy medium-sized team with some designers who were earlier in their career.

Newer designers needed mentorship and opportunities to learn from more seasoned designers. Our more tenured designers needed opportunities to share their skills, think about their work in new ways, and continue to hone their craft through teaching.

Realizing this, I reached out to our design leadership team — 2 managers and our director — and asked if I could lead a workshop to try to get the ball rolling on some more effective collaboration.

I’ve never met a manager who didn’t like a workshop they didn’t have to design or facilitate, so I was in business.

How do I make this workshop successful?

What should this workshop accomplish?

I had 2 high-level goals in mind, which resonated with our Design Leadership team —

• Increase collaboration amongst designers
• Increase the rate at which our design team is “leveling up” across all our Product Design Operating Principles (PDOPs)

How to make it happen?

I proposed to our Design Leadership the following plan of action —

• Design an exercise for each member of our design squad to self-identify 3-5 skills/areas where they feel particularly strong
• Use the results of this exercise to establish a source of truth that designers will look to when they need help in areas that align with others’ expertise
• Socialize this resource so it becomes a common reference point across the design team

“Not so fast” — smart leaders giving smart feedback

Ali rightly called out a few things I needed to be thinking about, but wasn’t —

Not all arenas for feedback are the same

I would need to account for some of the difference between the kind of feedback that is shared in a “pair design session” setting vs something like a more formal “design review” setting.

This exercise could have impact beyond just “improving feedback and collaboration”

This could be an opportunity to start to identify experts within our team and lean on them to use their skills in broader, further-reaching ways than I had imagined.

Evolving my strategy to account for the risks

Ali also highlighted some risks that would mean I needed to adjust my strategy if I wanted to deliver on the outcomes I was hoping for.

To address the risks Ali called out, I decided that I needed to solve for these questions:

• How do we account for self-reported skill overlap between designers potentially making it hard to identify our true experts?
• How do we account for the potential for self-reporting of expertise to be inaccurate? (eg. conflating passion with expertise)
• How can we account for someone potentially struggling to give good feedback on a topic even if they’re very skilled at it?
• How can we help ensure that feedback from our “team experts” is consistent with Design Leadership direction?

With these questions in mind, I made some adjustments to my original idea —

• Designers will categorize their skills into one of 3 categories — “kick-ass”, “passionate”, and “aspirational”
• We’ll use these categories as a starting point for further conversations with managers about how to best use each designer’s super powers, rather than treating the results of the exercise as a source of truth

Talking through this adjusted approach with the Design Leadership team put them much more at ease and created some more excitement about the workshop, which was enough to give me confidence in the direction I was headed.

How do I make sure this workshop doesn’t suck?

Even with confidence in the direction I was headed, there was still a lot of room for things to go wrong. I’ve been in enough well-intentioned workshops that just ended up sucking because they weren’t engaging, felt compulsory, or I just didn’t really understand why we were doing what we were doing. I wanted to make sure that didn’t happen here.

“What needs to be true for this to be successful?”

Thinking about common themes in workshops that I’d attended and didn’t enjoy, I came up with a few principles that I believed would guide me to success.

“Okay but how do we actually make the activity fun, clear, flexible, and lasting?”

Pulling it all together

To deliver on making this exercise fun, clear, and flexible, I decided to lean into the super hero theme. I made a variant set of 30 different “super power cards” that each featured a different superhero as the background image, so each participant could customize to their liking.

I also created a generic template (featuring the Avengers as the background because we’re all a team, obviously) that each participant could duplicate to get started.

To help make sure the instructions of the exercise were clear, I embedded definitions for each category of skills right into the hero card. This way, each designer could refer to the definitions for each category if they either missed something in my initial instructions, or in case they forgot.

I also left persistent directions on the Figma canvas where we’d all be working, just in case.

To make it easy for designers to grab-and-go with any of our Product Design Operating Principles, I created another variant set that leaned into our brand and interface colors to separate skills into each of the 4 categories of our PDOPs.

I also added a 5th category and color for “Custom”, so designers could add any skills that didn’t necessarily fit into any of the PDOP categories.

I felt like I had a recipe for success, and I was stoked to run this workshop.

Better than expected

The day of the workshop arrived, and it was a smashing success!

The introductory anecdote about my 1:1 with Kris, along with an explanation of my vision for how this would help us collaborate more effectively helped get the designers in attendance excited.

Everyone was able to follow the instructions and set their cards up with ease, and the directions about how to categorize skills from the “PDOP Powers” made sense.

I’d originally allotted 15 minutes for everyone to fill out their cards, but the group finished in about 10 minutes.

With some extra time in our meeting due to another agenda item falling off at the last minute, I felt inspired to ask the group and our leadership team “What if we took another 10 minutes and had everyone acknowledge each other’s skills?”

Everyone responded with enthusiasm, so I directed everyone to place just a single “compliment card” on each other designer’s freshly minted profiles. That turned out to be an unexpected highlight of the session, as each designer got to read praise from their peers for their abilities.

As well as the workshop had gone up to that point, I really believe it was the final minutes of taking time to acknowledge and praise one another that really drove the exercise home and left the group feeling a greater sense of unity. It felt like I had definitely delivered on fun, clarity, and flexibility.

Making it last

In the following weeks, I followed up with our Design Leadership team to talk about what we could do with the output of the workshop. Design leaders committed to bringing up the results with their direct reports in their next 1:1 meetings.

We also used the information we’d gathered about which skills fell into the “kick-ass” and “aspirational” categories for different designers to help guide decisions about who to pair up as “pair design” partners for the next quarter. I was lucky enough to get paired with one of our strongest visual designers, which really helped me expand the way I thought about our Design system and individual interactions in our web and mobile apps.

As our team continued to grow and level up, the results of this workshop quickly became outdated. We ended up getting about 3 months of use from the outputs, which I was happy to call a success at the time.

In the time since, I’ve successfully run this workshop in 2 different parts of the business where this helped designers get to know one another after acquisitions and re-orgs shook up our staffing and left people feeling uneasy. Each time, it’s helped bring teams together and surface new opportunities for collaboration.