The numbers on the clock change, and you find yourself still staring at the same screen with an empty white document. You have an understanding of the problem you’re working on but need a fresh angle. Look beyond the obvious and invite others to collaborate.

Including others in problem-solving is often the fastest way to a smart solution.

In this article, I’ll explain how to achieve your ideal end user experience through cross-team collaboration. This collection of workshops is designed as a toolset to foster dialog with colleagues across your company, regardless of whether you’re collaborating in one office or many separate spaces.

Tips are included for geographically distributed teams.

Ideation Workshop

During this workshop, participants have the opportunity to explore ideas in small groups then share their insights with the whole group. We’ve used this workshop as a base at Dwolla to generate wildly imaginative blue-sky concepts. In one workshop, we asked participants to combine two very different elements and see what ideas were generated. This method can also be used to explore new product features or to craft a deck with insights and observations about competitors.

Use When

You need divergent thinking for abstract problems—challenges that are undefined and don’t have one right answer. This workshop offers a way to generate a number of ideas in short order.

Who to Invite

Invite representatives across teams. Make sure multiple roles are represented (for example: engineering, product, marketing, design). Ideation works best when divergent thinking styles are represented.

Time Needed

1–2 hours

How to Prepare

  • Depending on the size of the groups, you might want to choose one person to lead each group and facilitate discussion. You might also allow groups to choose a leader organically.
  • Each challenge is different. You might already know the themes you want groups to discuss, or you might choose to solicit input ahead of time via a survey. Choose the format based on your audience. We’ve used Google Forms or even simple Slack messages to groups.
  • If you use cloud software with real-time collaboration features, consider creating a slide deck for everyone to use. Encourage teams to create several slides to share their ideas with the group.

What to Do

  • Define the challenge at hand and present a problem statement.
  • Next, divide your group into smaller groups and have each choose a focus area.
  • Set a timebox for exploration. Allow each small group to work independently on possible solutions.
  • Exploration can take many forms. The point is to use whatever method resonates with the problem at hand.
    • The groups could review competitors who have solved a similar problem and collectively analyze the approach.
    • Or the groups could mind-map different paths to a solution.
    • The group could also create a collaborative wireframe using slideshow software.
  • When time’s up, have each team present their work. Some might want to talk to possible solutions. Others might have screengrabs or sketches to share.
  • Document EVERYTHING for future reference.

Mapping Workshop

At this workshop, participants will contribute notes on parts of a process or series of events. The workshop could be about a process that already exists but needs improvement or a design for a future process.

Use When

You need to visualize a complex process that might exist in your software flow or customer journey. This approach allows for an interactive discussion to drive a shared understanding.

Who to Invite

Invite anyone involved in making significant project decisions. If there are technical considerations, be sure to include your engineering leads.

Time Needed

30–90 minutes

How to Prepare

  • If the team is meeting in person, gather supplies and find an open stretch of wall to place notes on. We once covered an entire meeting room with sticky notes!
  • If the team is meeting online, consider using a purpose-designed tool for capturing virtual sticky notes. We’ve been using Google Jamboard at Dwolla. You can also elect to create your own by drawing editable shapes in a cloud presentation tool.

What to Do

  • Review the path you need to map and challenges surrounding it.
    • If you’re working with a large group, you might consider having two facilitators, one to lead discussion and one to take notes and elevate questions to the group.
  • Give each team member a sticky note—virtual or physical—to complete. Use different colors to differentiate notes between members or categories.
    • Encourage each team member to add their observations knowing they are doing so in a judgement-free environment. It might feel awkward at first, especially if everyone is connecting in an online meeting. Set a standard by asking everyone to fill out at least one note. It’s important to emphasize there are no wrong answers or observations—you are looking for quantity, not quality. Your list will organically be whittled down.
  • Group the notes by theme during the workshop. Depending on the process you’re visualizing, you might group like things together. Or you might show a sequence of events, with major events listed on top and minor related events listed below.
    • During the course of discussion, you might need to pause and rearrange notes. Perhaps there’s a category you hadn’t considered or a step that got skipped. This is a healthy sign and shows your group is digging deep.
  • Pause at the end to assess and document work. What pieces are missing? Do you need more research or exploration for a particular phase of the map? Use this opportunity to set next steps and a follow-up session if needed.
    • Also consider how you will use your map to move your project forward. If you’ve created a physical artifact, consider whether you can maintain it in its existing space, or whether it should be photographed and referenced as needed. If it’s a digital artifact, you might want to bookmark the url or export a static file.

Sketching Workshop

This workshop invites participants to sketch their idea with simple shapes and annotated text. No drawing skills needed. The only requirement is an open mind to explore the flow a user-facing process might take.

Remember: We’re focusing on getting the best user experience. Sketches can be accompanied with text boxes for explanations.

Use When

You want to gather a range of possibilities for a particular product enhancement. There might be more than one way to approach a feature like in-app messaging or to address a problem like secure password recovery. Following this workshop style allows participants to envision how functionality might work and how it will communicate actions to the end user.

Time Needed

30-60 minutes

How to Prepare

  • If the group will meet in person, gather sketching supplies—blank paper, black markers and pens work well. Fewer choices for creative supplies can streamline the exercise and reduce choice fatigue.
    • If folks will meet online, encourage them to gather their own materials. Virtual meetings can use the Google Jamboard tool for a virtual whiteboard.
  • Stress that the purpose of the workshop is to gather ideas, not to create beautiful works of art. If a person can draw lines and boxes, they have the necessary skills to attend.
    • If you’re mixing subject matter experts (SMEs) with a design team, consider pairing SMEs and designers. SMEs can offer direct insights to designers who can visualize a solution.

What to Do

  • Introduce the challenge to the group. If building on existing UI, you might want to take a moment to demo existing functionality to give everyone the same frame of reference.
  • Share basic requirements—if there are any. For example: the in-app messenger will only allow the user to contact individuals they’ve friended.
  • Set a timebox for exploration. Allow each small group to work independently on possible solutions.
  • Take a few moments to answer any questions the group might have. If helpful, you might introduce a warm-up exercise where the group generates very specific ideas. For example: how is the in-app messenger accessed? Or, what examples has the group found that can be used for inspiration?
  • Then, give the group a time limit (at minimum, offer at least 20 minutes) and turn them loose.
    • Offer a check-in point halfway through and when there’s 5 minutes left.
  • When time’s up, bring the group back together for discussion. Go around the room and give everyone a chance to share their ideas. Encourage discussion and “what if” thinking.
  • Outline next steps for the project and how the ideas might be explored.
  • At the conclusion of the workshop, create a shared folder for everyone to upload their sketches so the artifacts can be preserved for future reference.

Generating new ideas doesn’t require a creative job title, but the process of creating ideas does require some advance planning and smart facilitation. As any experienced product person knows, integrating payments infrastructure and growing a customer base isn’t a one-time activity.

Embracing a growth mindset means being open to change at all levels of the organization. Tapping insights from across the organization and iterating on new features is integral to business success.

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