Navigating Ambiguity: When In-Person Collaboration is Key in Product Design

Navigating Ambiguity: When In-Person Collaboration is Key in Product Design

When we talk about leading teams through uncertain times, strategic initiatives, and change, it can mean a number of things that impact design. It could mean your company is inventing an entirely new feature or product. It might mean your team is pivoting on an existing product. It could mean your company is restructuring. Or perhaps you're moving into an area of the company that you've never been exposed to before. Whatever the case, you are dealing with ambiguity and change, and this can’t really be done in your focus bubble, heads down, working on a design.

Using Remote and In-Person Work as Techniques, Not Dogma

I’m all for remote work, but there are times when getting into the same room for multiple hours or days is a salve that cures so many ailments. Remote work is great when the direction is set, the tasks are clear, and we need to go into our focus bubbles to churn out work. As a designer, I find so much value and, frankly, peace in working this way. But at some point, we need to figure out something that can’t be solved asynchronously over Slack. This is where we use where and how we work as a technique.

When I need to pull people together in person, I think of it as a way to “dump out all the Lego pieces,” sort them, and work together on our direction. This collaborative environment helps in tackling complex issues that require immediate feedback and dynamic interaction.

Some Forms of Work Are Hard to Accomplish Asynchronously

Certain types of work simply can't be done effectively without synchronous collaboration. Pairing on an implementation with engineering springs to mind. This scenario doesn’t necessarily need to be a workshop, but it requires design and engineering to meet at the same time, if not the same place, to work through an issue. Similarly, product strategy sessions, whether brainstorming new ideas or refining an existing product, benefit immensely from in-person collaboration to create alignment and direction.

Research synthesis is another task best done in a team setting. I’m not a fan of research share-out decks because it's too easy to present or record them and then forget about them. Truly effective synthesis happens when a team reviews, discusses, and makes decisions based on what they've learned.

Making Human Workplace Connections Is Best Done In-Person

We only have to look at social media to see how the human element of interacting with others can be reduced to clichés, pettiness, and culture wars. There is so much more nuance to a person’s perspective that gets lost in our haste to respond to tasks and messages. When we have a strong sense of direction and alignment, asynchronous communication can work. But when we need to stop and think about what we’re doing, achieving, and where we’re going, we have to slow down and engage more deeply.

We are social creatures who rely on creating connections with each other to build strong bonds. During focus-intensive work, we need our own space, but when it comes time to think and make decisions, we need each other. Not just to get things done but to feel like we belong to something bigger. In-person workshops allow us to see each other’s presence, discuss life inside and outside of work, and build relationships that strengthen our ability to execute work and foster a sense of community.

When Should We Employ In-Person Techniques?

In-person workshop sessions are invaluable in several scenarios, yet I often see a reluctance to employ them. Whether due to resistance to collaboration or simply a lack of experience, many people hesitate. Let's clarify some situations where in-person design workshops are beneficial:

  • You've done some great visual design, but the information architecture and flows through the app are problematic.

  • You're working on an older product with knowns and unknowns you're struggling with or debating.

  • You want to do discovery on a product but aren’t sure what to focus on (usability? Competitors? Accessibility?).

  • You've done a bunch of research on a product and want to study it together and make decisions.

  • You need to define what the product or feature will be (zero to one, product-market fit, opportunity cost).

How Lead Designers, Principal Designers, and Directors Help Guide These Activities

Knowing when to trigger in-person work is one thing; understanding how to run an in-person workshop is another. This isn't an article where I give all those goods away, I can just tell you, this is where experienced practitioners of product design come in. Every company, product, and team is different, and so is each situation and if advanced practitioners are good at one thing, it's determining the right thing to do at the right time.

When I lead this work with teams, I start with an intake discussion with key partners or leaders to understand where they and the team are, what they think needs solving, and what timing requirements we’re trying to hit. It’s a lot like being a freelancer and forming a brief. This approach helps maintain a sense of “outsiderness,” allowing me to remain unbiased and guide the team through uncertainty and change while adhering to a schedule.

The Lightweight "Dumping Out the Legos" Workshop

I usually work in a very bespoke and organic way when pulling together an in-person workshop that helps a team cut through ambiguity and get alignment going. That said, here are some of the agenda items I often reach for, even if they don't always all find their way into a session:

  • Goals & Anti-Goals - This is intended to be for the project, but can also be for the time you have together running this workshop.

  • Risks & Mitigations

  • Review of inputs - Alignment and orientation around problem space. Learning from recent research and discovery efforts

  • Synthesis - Synthesizing teaching into provisional definitions of the free experience

  • Parking

  • Timelines

  • Measures

  • asdf

What About Detractors?

It's important to acknowledge that for some, in-person work and collaboration can cause anxiety, doubts, or even resentment. I've worked with partners wholly resistant to collaboration. While I thrive in a high-collaboration environment, I understand how sharing space with others' ideas can be uncomfortable for some.

Consider these common objections:

  • We’ve done the kumbaya thing before.” Some see collaboration as compromise. If you encounter this viewpoint, try putting detractors in the driver’s seat. Ask how they would want to utilize the time, offering them a sense of control and involvement.

  • We could still do this asynchronously.” This is true and often feasible. However, we sometimes need to address the interpersonal relationships that underpin teamwork. If team members are new or have never met in person, bringing them together can foster positive relationships.

  • We don’t have time for that.” For small, incremental work, this might be true. But for bigger picture planning and offsite work, making time for in-person collaboration can be invaluable. We make time for what we value.

There are millions of excuses to avoid collaboration and I encourage you to consider how deeply difficult and scary this can be for some people. I believe if we start from a place of trust and respect, we can more easily engage these spaces. This is worth working towards because the impact can be that we have strong direction and alignment to our work.

Conclusion

If you are a team leader, founder, director, or organizational leader who believes these approaches can help, get in touch! I’m always open to helping teams find clear direction and alignment through in-person work.

Open for Opportunities

Open for Opportunities

Open for Opportunities

Freelance, Fractional, and Full-Time Roles. If you need a proactive director or principal-level designer to drive results, let’s connect.
Andy Detskas
Andy Detskas
Andy Detskas

Mountain Time Zone

Mountain Time Zone

Mountain Time Zone