Building better together: 5 learnings from a product manager and designer duo

Caitlin Brisson
Gusto Design
Published in
8 min readAug 11, 2020


Co-written by Caitlin Brisson and Vipul Chhajer

This summer, Gusto, the people platform loved by small businesses, launched a suite of tools to streamline how business owners hire and onboard new employees. This launch was spearheaded many people and multiple teams — so today we’re going to talk about teamwork and how you can build better when you work together.

Wait…who are we? We are Caitlin Brisson, product designer, and Vipul Chhajer, product manager. We love creating products that support small business owners across the United States.

In the suite of tools we launched, our focus was the onboarding checklist, which makes it easy to manage all the things you have to do when bringing on a new hire, such as completing new hire paperwork, setting up software tools, or tracking their to-do’s. The onboarding checklist is central to our new features, tying them together to make it easy for business owners to manage their entire onboarding process in one place.

The onboarding checklist. For every new employee, you have one reliable list.

As we designed, built, and iterated on the checklist, we learned the challenges of collaborating and coordinating with several teams. We also learned all the little things product designers and product managers can do to work better together — we’re excited to share these with you. We hope you find them useful and that our learnings help you create amazing products of your own.

1. Invest the time to really understand each other

There’s often tension between product managers and designers. How can there not be? The tension comes from differences in our roles, for example, we both advocate for our customers, but with different goals and metrics in mind. Differences in personalities and working styles also contribute. What we sought to understand is — how can we use that tension to our benefit? How can we use it to make our partnership and ideas better?

As we invested more time in our working relationship, we reframed challenges as positive creative conflicts — this helped us work through arguments, brainstorms, and, in the end, created a level of trust that enabled us to become advocates for one other and our work together. We celebrated our wins and our failures as a team and had each other’s backs.

We added these sections to the top of our ongoing 1v1 doc to help us stay accountable to each other and our work.

A few things that helped us:

  • Schedule weekly 1v1’s to discuss plans, goals, feedback, and any disagreements
  • Share professional and personal goals to help each other give targeted feedback (check out our example above)
  • Share working styles and user guides to better understand how we think and work
  • Create space to catch up and talk like humans and friends (hello, remote beers 🍻)

As a result of these, our partnership deepened. We trusted each other to speak for one another, allowing us to delegate more. We leaned into creative conflict as a tool for solutioning and walked away feeling positive. Our collaborative problem solving improved, allowing us to learn more from one another while also setting the stage for collaboration across our team. Oh yeah, and we also had a ton more fun in the process 🥳.

2. Immerse engineers in the problem space

Engineers, product managers, and designers work as a team to build products. When teams are small, it’s easy for everyone to interact with customers and get to know their needs. As teams grow, it’s common for product managers and designers to talk directly to customers, and share key learnings with engineers so they know the customer too.

Our take is a little different; knowing isn’t enough. Being immersed in your customer and their needs should be the bar. This means engineers not only know the customer but also understand the why — why this customer and not others? Why this problem? Why does solving this matter to our company? That’s when creative solutions to problems appear.

Summarizing customers and their needs in this manner helped everyone quickly align on our priorities.

A few things that helped us:

  • Frame customer needs and solutions in narratives that highlight customers’ experiences
  • Don’t just share research summaries. Go over insights with your team and create time for Q&A
  • Encourage engineers to challenge assumptions and solutions. Have a different way to solve the problem? Could we do it simpler and faster? Get on a whiteboard
  • To help the team understand priorities right off the bat, express the customer and the problems you’re solving in the simplest way possible

Since our whole cross-functional team understood the customer and their needs deeply, engineers on our team came up with solutions on their own and made more product decisions. It also helped us prioritize use-cases more effectively. Win-win for the team.

3. Don’t just create team norms — stick to them

When you’re beginning a long-term project or working with a new team, explore how you want to work together. Define your norms and use them as tools to navigate conversations and challenges — and more importantly, create space to reflect on how well they’re working.

We had a mix of new and seasoned Gusties across multiple locations and time-zones, so it was the perfect opportunity to up-level how we collaborate.

The norms our engineering, product, and design team came up with to help us work best together.

How we suggest setting them up:

  • Have your team fill out a survey to gather collaboration preferences and ideas
  • Create a list of topics with the results and brainstorm which norms to adopt as a team
  • Summarize ideas into a few principles and refine them with team feedback
  • Highlight norms in standups and retros to understand how they’re working
  • Use them in meetings and during collaboration to call out areas of opportunity where you can better align with the norms

Our norms set our team up for good execution and collaboration by creating psychological safety and transparent expectations. We felt safe sharing difficult feedback and challenging one another. We also experienced deeper collaboration across engineering, product, and design — often taking to the whiteboard to work through questions together. This allowed everyone on the team to step up as a decision-maker, enabling us to land more effective and efficient solutions together — and hit our milestones.

4. You’re going to disagree, so do it constructively

With any product, there are lots of decisions to make and imperfect information to make it with. To be successful, product managers and designers need to make decisions quickly and make the right calls more often than the wrong calls. Upfront alignment between designers and product managers helps — but let’s be real, disagreements will still happen.

A few things that helped us:

  • Share what your choice optimizes to focus your conversation on the trade-off (Ex. User A over User B, Metric X over Metric Y)
  • Rate how important the topic is to you (1–5). If someone votes a 1 and a 5, just go with the 5.
  • For reversible decisions, pick the path that can be easily tested
  • While consensus feels natural, it can be slow. Explore using “disagree and commit

Highlighting choices, trade-offs, and the strength of our opinions added a new dimension to our debates. They allowed us to stop seeing disagreements through a negative lens (“Oh no, we’re not aligned. Something is wrong”) and see it in a positive light (“We’re making difficult tradeoffs as a team”) — allowing us to move forward faster.

5. Create “collaboration captains” to smooth cross-team work

When multiple teams work on one area at the same time, it’s key to stay aligned on goals, use-cases, and ownership. Sharing designs and progress is critical, but we suggest taking it one step further — create a collaboration captain who works with the other team to facilitate an effective partnership. They are in charge of considering and communicating how the projects will come together and make sure any roadblocks are surfaced effectively.

We didn’t do this at the beginning — and at points, we had quite a bit of thrash and confusion with two other teams. As our projects progressed, we realized we needed better cross-team collaboration and communication. Engineers on our team took the lead as collaboration captains and it improved our ability to execute in parallel, together.

What sorts of things does a collaboration captain do?

  • They become the main point of contact for the other team’s questions and feedback
  • They sit in on some of the other team’s sprint planning meetings and retros
  • They invite the other team to share work at your team meetings
  • They keep both teams up-to-date on any changes or challenges between projects

Our project areas that had a collaboration captain were smoother and more effective at navigating updates and challenges. It also empowered members of our team to become subject matter experts in other areas of work, giving us better insight into how our decisions might impact other teams. As a result, we surfaced and solved problems faster and improved morale between teams.

Closing thoughts

We learned so much through the course of this project — we hope this helps give you some ideas on how you can improve collaboration and work across your team. If this does resonate with you, we’d love to hear from you!

In summary, we recommend exploring the following to help you build better together, from inception through launch.

  1. Invest the time to really understand each other
  2. Immerse engineers in the problem space
  3. Don’t just create team norms — stick to them
  4. You’re going to disagree, so do it constructively
  5. Create “collaboration captains” to smooth cross-team work

And hey, if working like this is something you think might be up your alley — we’ve got good news! We’re hiring product designers and developers! 👋 Check out our careers page to learn more.

We want to thank the core members of our team for all their hard work, support, and ideas along the way—and for making every day a fun new challenge. Massive kudos to our team: Damon Aw, Stephanie Chong, Jeff Federman, Danny Grant, Ryan Newton, and Julianna Roen.