Illustration by Alisha Giroux.

How to use design thinking for productive kickoffs

A checklist for approaching projects with a human-centered lens

When you join a new team, whether existing or newly forming, it can feel like there is so much context you need to gain and no obvious starting point. Depending on your discipline, you’ll seek out different information than your colleagues — you’ll likely all gather very relevant context but you’re ultimately developing a view of the problem and/or opportunity area that is unique to you and your role.

If you’re a designer, you may not think that something is helpful to share with a developer or vice-versa; you may share your findings via an email, Slack, or Google doc and, while your colleagues have every intention of reading them, they get lost in the shuffle. In the remote workplace, these context-sharing challenges are even more apparent. However, effective team and project kickoffs can help manage the impact of these challenges.

When I start working with a new team or project — most recently while joining the team at Shopify as a product designer — taking the time to build and document a shared understanding is crucial. I’ve had opportunities to plan and co-facilitate many kickoff workshops, bringing together diverse groups of team members to dive deep on user and stakeholder needs, problems, opportunities, and the path forward. Doing this effectively is a skill I’ve honed since the beginning of my career.

When I first started working in UX, I took part in an immersive three-month training program to learn IBM’s Enterprise Design Thinking framework. This familiarized me with a toolkit for breaking down problems, identifying potential solutions, and understanding systems through a human-centric lens. Since then, I’ve applied design thinking techniques in many different workshops. I’ve realized their value isn’t only in generating ideas but also in creating a shared understanding among teams that leads to easier communication and decision-making going forward. These techniques and frameworks are only effective in the way you apply them, so I’m going to share a few things I’ve learnt along the way.

When I helped plan the team kickoff mentioned above with my team at Shopify, we had a few goals in mind. Some changes to our team’s strategy had just been announced and a new product manager and several other new colleagues joined the team. The product manager approached me and our development manager about planning a team kickoff to bring the team together and plan for the work ahead. We saw a great opportunity to leverage design thinking and planned a workshop over three sessions — we used these high-level goals to guide our activity planning:

• Understand where our team fits in. Activities: review objectives, stakeholder mapping.
• Evaluate our ways of working. Activities: team retro, team blueprints.
• Align on the current state. Activities: identify and prioritize problems, event storming.
• Brainstorm solutions. Activities: storyboarding, ideal state envisioning, and prioritization of work.

An example of an activity to map stakeholders using a Miro board.

Workshops are a great way to get to know each other and build a sense of morale — when we did this team kickoff, not everyone had had the chance to connect one-on-one. We shared the plans with our attendees and had a developer from the team volunteered to host the event storming activity, which none of us had tried out before. After we’d all collaborated during the workshop, we were comfortable reaching out to each other when questions came up, which goes a long way in a remote setting. There are lots of other benefits, too.

Left: map of the ideal experience | Right: voting on value to user and feasibility

How will my team benefit?

Whether you need approval to run a team kickoff, or have a skeptic on your team you’d love to have participate, it’s helpful to be able to communicate the value of bringing your team together for a workshop.

Build context

It’s easy to forget that not everyone has the context you do, even within your own team. Whether it’s because your colleagues are new or in a different discipline than you, you’ll all have some differences in understanding of a given problem. You’ll all benefit from sharing your perspective on a given problem or opportunity. The visual format of a workshop helps to make it memorable.

Break down complexity

Design thinking can be extremely valuable when breaking down complexity and surfacing user (or business) needs. Often, we assume that a surface-level understanding is enough and, in doing so, we miss out on blockers and opportunities that could have been identified if more people or disciplines had a clear understanding earlier on.

On the flip side, we can sometimes assume a great deal of effort is required to solve a user or technical problem — when we take the time to break down the steps we can realize that some improvements can be made right away. Breaking down the steps in a flow or systems at play helps us make sure that we’re solving the right problem and not wasting time and effort.

Create a shared understanding of what’s ahead

Sharing context and breaking down complexity allows you to make an informed plan from the beginning. Building a plan together will allow everyone to feel a sense of ownership and morale.

The artifacts you create will help to determine the amount of work ahead and serve as a reference point for those who weren’t in attendance. Everyone involved will develop at least a high-level understanding of the work that’s involved for other disciplines, making for smoother communication and decision-making going forward.

Encourage diverse perspectives

By design, design thinking activities are structured to allow everyone to share their opinions. In a workshop setting, people are encouraged to think and write out ideas or opinions silently before sharing with the group. Ideas can first be considered without an attachment to a certain role or level of seniority. This leads to a collaborative environment in which people tend to build off of each others’ ideas, rather than fighting to be heard.

Think outside the box

Brainstorming fosters innovative ideas. Whiteboard sessions feel (and are) low-risk settings to explore “big ideas” that we might otherwise write off.

Running a design thinking workshop can seem like a daunting task if you’ve never done something like this before, so I’ve put together a checklist to help you get started—or to refresh your approach.

A design thinking workshop checklist

Learn or revisit the basics of design thinking

There are several proponents of design thinking out there and so there are several many resources to learn from. They all tend to have a few things in common:

• Making sure you understand the problem
• Empathizing with people and users
• Divergent and convergent thinking
• Designing iteratively (prototype, test, repeat)

Here are a few of my favourite resources for learning about design thinking principles and typical workshop activities:

• Interaction Design Foundation (IDF) (articles and courses)
• IBM Enterprise Design Thinking (framework, courses, and activity guides)
• IDEO Design Thinking (articles, resources, and courses)
• Design Kit by Ideo (toolkit and activity guides)

Think about the structure of your workshop

• How much time do you have? Two hours, one day, multiple days? Will you break up shorter sessions over the course of a week or have one single, longer session? This will shape what you can realistically achieve during your workshop.
• Another way to approach planning is by defining your goals, then determining how much time you need to work through them (for example, understand the current experience, generate ideas, prioritize problems or solutions, build empathy, determine next steps, unblock a project).
• What stage is your project in? Depending on how far along you are, you can reference phases of design thinking and suggested goals and activities for each phase.

Consider who to invite

• Determine who to invite — consider who you need to have in attendance in order to get the outcomes you’re looking for and who’s optional. Because my team at Shopify is focused on pricing and billing, this included not only our product team but also stakeholders from finance and internal operations.
• Follow up with folks to get as accurate a headcount as possible and plan breakout groups in advance to include different disciplines.

Plan your itinerary

• Consider icebreakers, breaks, instruction time, and discussion time.
• Decide how much wiggle room you’re willing to give to the different activities you have planned. Will you timebox each one strictly or allow for discussions to continue past the allocated time?
• Have a co-facilitator or participant help you keep track of time (if possible!).
• If you’re planning multiple sessions, make time to re-evaluate your plan between them. Depending on how things are going, you might want to make adjustments.

Get prepped

• Do the setup for all of your activities in advance — make sure you’ve tested out all of the functionality you’ll need in your tool of choice (Miro or Mural work very well).
• Reach out to your participants to make sure that everyone has the tools you’ll be using set up and access to any private content.
• Think about your breakout groups ahead of time — do they mix different disciplines? If possible, set them up ahead of time. Ask someone to help you with these if you’re setting them up while the workshop has already started.
• Add written instructions next to your activities that participants can reference when completing the activities.

Other tips:

• Don’t be afraid to cover the basics even if it feels repetitive — starting with a shared understanding is key to a successful workshop.
• Ask others to co-facilitate activities and/or present when the subject revolve around their area of expertise — this will create an open and collaborative environment.
• Consider your audience and how much of an introduction to design thinking and/or working with whiteboards and sticky notes they might need.
• Make time for icebreakers, breaks, and stretching (especially in a virtual environment).
• Get creative and don’t limit yourself to running activities exactly as you find them (this gets easier with more experience). Structured activities are only a tool to encourage new ideas and human-centered thinking.

After your workshop

Congrats! Your workshop is complete. Don’t forget to summarize the outcomes. Consider the artifacts you’ll have after hosting the workshop and how you can best leverage them afterward.

For a larger workshop, you might want to summarize key themes from the whiteboard sessions, whereas for a smaller one, you might be able to polish the board as-is. You might also want to leverage the ideas while they’re fresh and start working on follow-up artifacts like journey maps, roadmaps, or designs. Here are some ideas:

• Make a copy of and polish your whiteboards
• Create a document summarizing key themes from each activity
• Create a journey map or service blueprint
• Use the outcomes to shape your team’s roadmap
• Use the ideas as inspiration — start sketching, writing, or coding.

Following a design thinking approach is a means to working efficiently and with a human-centered lens, especially in a remote environment. It’s not a rigid framework and can be applied to almost any problem or industry — you can make it your own. While workshops are an effective way to evaluate assumptions, generate ideas, and create alignment, what’s most valuable about them is the mindset that they promote. Hopefully, this guide will help demystify workshop design and facilitation so that more teams can benefit from it.