Design thinking workshop — step by step guide

Learn how to plan and run a successful design thinking workshop. Helping teams reach important objectives and have fun.

Taras Bakusevych
UX Collective

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Laptop with remote workshop tool and participant videos
Shoutouts to Pablo Stanley for his illustrations of people, this helped me make illustrations in this article more humaaan).

All recommendations in this guide are based on learnings from over a hundred workshops, large and small, onsite and remote, with startaps and enterprises that we have facilitated at Windmill and research made by other brilliant designers.

Design thinking workshop is a time saver

A design thinking workshop is a great way to define and solve problems fast. A successful workshop not only allows groups to build a shared understanding of the problem, tap into each participant's knowledge to generate ideas and define solutions but also have fun, bond, break silos and take ownership of making this idea a reality. It’s an interactive session that is based on design thinking methodology. Iteratively taking the group through five stages: — Empathize, Define, Ideate, Prototype, and Test.

Diagram of 5 key steps of design thinking

Planning and preparation

1. Identify the scope and objectives for the workshop

Objectives and scope is the first thing to be defined before the workshop and will define all further activities. The best way to get this answered is to run some preliminary interviews with key stakeholders. Map key objectives, expected deliverables, and assumptions you want to validate.

2. The more specific the problem, the more concrete the solution

Although design thinking workshops are incredibly effective, it’s important to have realistic expectations. Don’t expect to gather a group of people for several hours and get concrete solutions for multiple large scale problems. Think of this as a limited resource of energy and time your group has. The more specific the problem you are trying to solve the more concrete your solutions will be.

A visual comparison of flap plane and high column to represent depth vs scope of research

Usually, large companies will have multiple user groups, products, and an abundance of problems and questions. In those cases better to run hight level interviews and workshops that focused on framing the problem first, and only after that do you plan follow-up workshops to find solutions to those problems.

3. Always run a pre-workshop research

You don’t want to start asking basic questions, to get up to speed with the audience. Researching as much as you can before the workshop will help you better identify knowledge gaps that you need to close. It helps also to build your credibility quickly, which essential to effective coordination of the group.

4. Choose the relevant activities

After you have set a clear objective, it's time to pick the right tools (activities) to reach it. Choice of activities will depend not only on expected output but also on time you will have and participants you can invite.

When you need to build Empathy

It is one of the cornerstones of design thinking. Empathy is the capacity to understand or feel what another person is experiencing from within their frame of reference, that is, the capacity to place oneself in another’s position. Building empathy is a great starting point for your workshop. It will help you understand our customers, what are they trying to achieve, what drives them and what challenges they facing in the process.
Some activities that will help you build empathy:
Proto Personas, Empathy Map, Journey Map, Jobs To Be Done, VPC. Customer Profile.

Two participants speaking next to the user profile canvas

When you need to Define

Analyze your user observations and research and synthesize them to define the core problem and solution outline. These activities are focused on organizing unstructured data and insight into clear journeys or maps. Visualize organizational processes in order to optimize how a business delivers a user experience.
Some activities that will help you define:
Business Model Canvas, Value Proposition Canvas, Jobs To Be Done, Journey Map, Service Map, Design sprint Note-n-Map, Card Sorting

Two participants mapping a journey the canvas

When you need to ideate

Going in with open minds to produce as many ideas as they can to address a problem statement. It’s important to not be judgmental and embrace wild ideas. The goal is to look at the problem from as many angles as possible and step beyond the obvious.
Some activities that will help you ideate:
Lightning Talks, How Might We, Affinity Mapping, SWOT Analysis, Value Proposition Canvas

Two participants, one in the wheelchair generating ideas

When you need to Sketch & Prototype

Start by looking for inspiration, such as solutions in alternative spaces. Then, each participant will individually generate ideas. Use voting to narrow down ideas as a group and add details on a final storyboard. Don’t be afraid of sketching, you will be surprised by the great and fresh approaches you will get from tech team members. Some activities that will help you ideate:
Lightning Demos, Crazy 8's sketching, Storyboard, Sketch the Solution, Present, Vote & Decide

2 participants watching over factory line producing product

When you need to Prioritize

It is always challenging to prioritize all the ideas you generated in previous stages, understanding what pains need to be addressed first, or framing your MVP scope. Those activities can help you avoid endless debates and quickly identify essential items:
Story Map, Value Matrix, Dot Voting, Go/No-Go Decisions, 6 Thinking Hats, Planning Poker

Workshop participants prioritising ideas in a pyramid

Take the grouping above with a grain of salt. Many of the listed activities have many applications. One of the most versatile and almost always worth doing is Journey Map.
You can learn more about journey mapping in this article:

5. Plan engaging agenda

Participant's attention span decreases around 20 to 30 minutes into an activity, and by 60 minutes, it drops significantly. Participant's ability to focus and sustain attention is crucial to reach workshop objectives. Provide different types of activities, with regular breaks.

  • Planning time slots will help you stay on track during the workshop.
  • For remote workshops keep in mind, that activities will take longer, and don’t expect more than several hours of productive participation.
  • Better to schedule key and more complex workshop sessions in the first half of the day when people are fresh and have plenty of energy.
  • Always leave some buffer time. It’s not being lazy; it’s being intelligent. You would like to have a logical wrap-up for previous exercises, time for questions, and an intro into the next activity.
Visual agenda columns and people walking among them

6. Balance whole team, breakout, and individual activities

Switching between various types of engagement in the workshop will not only help keep participant attention high.
- Breakout groups allow larger teams to create various journeys or empathy maps simultaneously and creates healthy competition
- Not everyone is ready to express their ideas but we all have brilliant thoughts. By planning individual activities we leave space for everyone to express their thoughts in quite thinking rather than loud brainstorming.

Groups of people on the left, breakout groups and individuals on the right

7. Make sure each activity naturally flows into the next one

Having chosen what will be on the agenda, you need to make sure all activities come in a logical order. Various design activities have different fidelity levels, some may rely on findings from others. Make sure you start with the general “Big picture” and gradually move to “Granular details”, not the other way around.

Unfolding four panels  with Empathy map flowing into Journey map to sketches and storybaord

8. Follow tested recipes — Design Sprint Workshop

For those who are not comfortable with building their custom workshop agenda yet, there are amazing frameworks that you can follow. Design sprint developed by Google Ventures is a five-day process for answering critical business questions through design, prototyping, and testing ideas with customers. In the Sprint book by Jake Knapp, you find detailed instructions, tips, and case studies on how to run a successful workshop. If you feel like 5 days is hard to get, there is a Design Sprint 2.0 framework that will require just 2 days of active participation of the whole team. You can learn more about this framework on Design Sprint Kit website.

large sprint Book and people standing near it

9. Book a place and prepare all materials

  • Making sure you have booked a nice meeting room with whiteboards and walls you can cover up in your ideas. If you plan a multi-day workshop best to book the same room, believe me, you don’t want to move all the sticky notes to another place.
  • Collect lots of stationery: Post-it notes (different colors),
    sharpies, whiteboard markers, A1 and A4 sheets, scotch tape, Voting dots, scissors
  • Having some healthy snacks like nuts will make sure participants have their mind focused on the problem, not food.
Assortment of stationaries and nuts snack used with little person holding a sharpie

10. It’s ok to partially prefill the activity boards

This will save time and help participants contribute data in the right format. The task looks much easier if some progress was already made.

Having said that you do not want to complete the activity board fully, at that point you took the decision for the group, and your workshop turns into a feedback session.

Two empathy maps taped to the wall. Left one has few sticky notes and right one is filled in completely

11. Invite the right audience

Who and how many to invite will depend on workshop objectives and time frames. But here are some general recommendations:

  • Don’t invite too many participants. On average you don’t want to have more than 7–8 people in the workshop. It’s hard to coordinate larger groups, you will need more than one co-facilitator to support you and plan multiple breakout activities to make sure people can contribute.
  • Get a diverse representation of experts. Invite teammates that come from different parts of the company: financial, marketing, customer, tech, logistics, and design.
  • Assign a “decider”. Designated with the authority to have the final say. This can be the CEO or someone from higher management. You need a decider when the group struggles to make choice. Without the commitment from a decider, it’s likely to lose the momentum gained from running a Design Sprint after it ends

12. Share objectives and agenda with all participate beforehand

Letting participants know what’s coming will set the right expectations, reduce anxiety, and help participants be better prepared. Receiving an invitation with objectives, the outline of design thinking methodology, detailed agenda, and an overview of activities will be a great start for your exciting adventure.

Several sheets of paper being sent in the mail to workshop participants

During

13. Facilitation is fundamental to a successful workshop

Facilitation — the act of providing unobtrusive, objective guidance to a group in order to collaboratively progress towards a goal.

The role of the facilitator is to plan and lead activities and instruction in order to help the group do their best thinking together. Facilitation can be daunting, especially at first, it takes practice and learning from past mistakes so that future sessions progressively get better. Here are some tips for better facilitation:

  • Always listen. Aim to be constantly listening with an open mind, let participants share their ideas and thoughts. As a facilitator, it is essential to keep your thoughts, ideas, and comments to yourself as much as possible and let the group generate the content on their own. Don’t be tempted to outshine everyone else.
  • Guide, but don’t drive. Driving a group is taking the reigns and potentially pushing participants in the wrong direction. As a guide, you want to empower and encourage participants to move in a sensible direction.
  • Create open space. Your goal is to create a space where everyone feels comfortable sharing even their wildest ideas. You want to ensure equal participation from participants who are normally quieter and reserved.
  • Mediate the conflicts. It’s often that during the workshops opinions clash and conflict arise. Show your respect for both opinions, but turn arguments into productive conversations.
  • Have fun. Unlikely any big problem can be solved in one workshop. Your secondary objective on any workshop is for participants to have a great time, feel like they achieved something, and own the solution. Convert them to believers in the methodology, willing to do this again as a most effective way to tackle challenges and frame ideas.

Learn more about facilitation here: Why the Best Designers are also Facilitators, Why the Best Designers are also Facilitators

14. Set the stage

Start with introductions and a brief overview of objectives, design thinking, and agenda. It’s good practice to set the stage of the workshop by briefly running through the points above. Bring attention to some rules also:

  • No distractions — Ask participants to put away laptops and phones during the workshops, they can leave the room to use them and come back any time.
  • Timeboxing “Work expands so as to fill the time available for its completion”, that's why we watching over time and agenda progression.
  • Have fun — It’s important, don’t let anyone forget about it.

15. Diffuse team anxiety with an ice-breaker

Those simple team-building activities don’t need to be awkward or boring. Can be as simple and fast as asking each participant a question like: “ If you would be a boat, what type would it be, and why?” Here is a list with more examples of icebreaker questions.

Many people round table with iceberg melting in the little pond in the middle

16. In remote workshops make sure the group gets comfortable with the tools

As you work with tools like Miro and Mural on regular basis it easy for you to forget that your participants probably not. Start with a simple “sandbox” exercise where you can practice creating cards, adding and replacing text, etc. To save time you can combine this with the icebreaker exercise.

Screen illustration with participants practicing in online collaboration tool

17. Explain each activity and it’s value before starting

When you were setting the stage you gave everyone a brief overview, now before we start every activity it's essential for everyone to understand what we planning to do, why, and how to do it.

Facilitator pointing to the wall where instructions for Empathy Map are displayed, rest of the group is watching

18. Break down complex exercises in a series of simple steps

Some workshop activities may look scary and complex, but all of them can be broken down into a series of simple and clear steps. The key is to quickly explain this process to the group and help them follow it.

19. Highlight the progress you make, encourage participants

When delivered well, praise gives people the drive and motivation to continue doing great work. Highlighting the progress team made will give positive reinforcement for an even greater engagement in the future. Focus on bright spots, and keep all the work on the walls during the workshop. This completely transformed room or virtual canvas is the best evidence of your achievements.

Participants standing in the room, walls of which are covered with user journeys and other maps

20. Transfer your progress

Keeping up all the progress made at hand is not only useful for motivation or referencing information. It’s agreat way to save time by transferring some of the data or questions from previous activities into the next ones. A good example is transferring doing, pains and feelings from Empathy Map and Journey map.

People transferring post-it notes from one map to another

21. Time tracking increases productivity

This is creating a sense of urgency and keeping everyone on track. Most of the tools now will support some kind of visual timer for the remote workshops. For your physical workshops install this amazing Time Timer App to turn a passage of time into something visual. Having said that, try not to rush the group too much, add extra time from your reserved bank to make sure speakers and teams can finish whatever they started.

On the left people observe a large timer, on the right woman sitting, looking at the agenda on the wall

22. Done is better than perfect

As humans, we tend to strive for perfection. It’s just impossible and usually not worth it to spend time capturing and arguing over edge cases and all tiny details. A common phrase you will hear “ It depends..”. It’s important to constantly remind the group about objectives and focusing on getting things 80% accurate.

23. Be flexible and ready to improvise

Not all participants showed up? You see group moving too slow to cover all planned activities? The problem is much broader than you expected?
Don’t be afraid to alter the agenda. There is no reason to stick to the predefined agenda if you see things are not working out. Always think of how you can maximize the impact of the workshop. Changing the flow of the workshop on the go will become more natural and less stressful with practice.

Group of people arguing about something

24. Don’t be afraid of sketching or prototyping

Sketching gives people the freedom to consider every wild idea without the fear of making a mistake. Some of the best ideas and concepts may come from a developer or someone in marketing. Do not worry about how beautiful things look, make sure all participants are engaged not only in problem framing but also in prototyping and sketching the solutions.

25. Debrief and outline next steps

Close the workshop with the summary of the progress made and key insight that was discovered. Outline the next steps and let people know how those findings will be used.

26. Document and share results with participants

Spending some time to document and clean up all workshop discoveries will not help you or someone else working on this problem in the future. Sharing this report with all participants will be a great way to give something back to them. Don’t only try to include all journeys or maps as they were captured during the workshop. Try to highlight and surface the most important findings.

We can help you run your design sprint

Hopefully, this guide and the linked resources will help you plan and run your own successful workshop. If you need further assistance or want to discuss the implementation of design thinking in your organization, reach out to us at Windmill Smart Solutions.

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