Designerly Ways of Thinking Workshop

Diane Bowen
4 min readApr 9, 2022

This remote-first workshop introduces problem solving on a large scale for the social good, surfacing surprising solutions through appositional thinking.

Time required

With 6 to 8 participants in each large group, the workshop can be completed 1 to 1.5 hours.


Through hands-on practice, participants will explore appositional thinking and abductive reasoning, valuable for initial problem explorations.

1. Apposition: the act of placing together or bringing into proximity; juxtaposition.

2. Abductive reasoning: observing, then exploring to find the simplest and most likely explanation for the observations, taking your best shot at an answer.

Set up

  1. Review Nigel Cross’ The Nature and Nurture of Design Ability and What’s a Wicked Problem?
  2. Internet-based meeting tool with sessions that can split off from the main session.
  3. Internet-based document sharing platform with permissions for participants to edit like Google Drive, Miro, Confluence, etc.
  • My Favorite Things list with an example list of presenter’s favorite things, labeled with presenter’s name
  • Wicked Problems working space where teams of two may add text and images
Connecting favorite things with solutions for wicked problems builds design skills.

Workshop Introduction

5–7 minutes

Presenter, the following is a lot of material. It is intended to move fast. If you use slides, provide a presentation link to your participants.

Award winning design affects business growth.

  1. Briefly overview content and diagrams from The Nature and Nurture of Design Ability by Nigel Cross
  2. Share commonalities among award winning designers:
  • Craft right-fidelity design documentation with annotative descriptions for design artifacts
  • Test designs during discovery, definition, and after delivery
  • Iterate on designs, understanding implications, stressors, and multi-level measurements

3. Briefly explain Cross’ themes in Design Ability

  • Intuition
  • Problems are closely related to solutions
  • Sketching, drawing, and modeling
  • Living in uncertainty
  • Transcend the obvious to move to exciting and stimulating

4. Summarize Cross’ thoughts on methods to nurture design ability

  • Produce novel, unexpected solutions
  • Tolerate uncertainty, working with incomplete information
  • Apply imagination and constructive forethought to practical problems
  • Use drawings, images, prototypes, and other modeling media as means of problem solving

Activity 1

5 min

Explain this activity will hep participants apply a Designerly way of Thinking approach to problem solving.

  • Resolve ill-defined problems
  • Adopt solution focused strategies
  • Employ abductive, productive, and appositional thinking
  • Use drawings, images, prototypes, and other modeling media as means of problem solving

Share the document platform with participants if they do not already have access. Ask participants to make a list of their favorite things in the platform, labeling the list with their name. Presenter share your example list.

Give participants 2 minutes to make their list. After all participants have completed their lists, ask each one to share their list.

Wicked Problems

3–6 min

Explain that in1973, design theorists Horst Rittel and Melvin M. Webber used the term “wicked problem”, referring to problems that are difficult to define and inherently unsolvable. They suggested the following 10 characteristics of wicked problems:

1. A lack of definitive formulation

2. No stopping rule that determines when a solution has been found

3. Good or bad solutions rather than true or false solutions

4. Lack of immediate and ultimate tests of solutions

5. Solutions are “one-shot” operations rather than trial and error

6. Lack of criteria that indicate all solutions have been identified

7. The uniqueness of every wicked problem

8. Any wicked problem could be viewed as a symptom of another problem

9. Any discrepancies in wicked problem can be explained in multiple ways

10. Planners have no right to be wrong in that they are responsible for outcomes that result from the actions they take

Activity 2

Total time: 25 minutes for both large group and teams of two activities.

Large group activity: 3–5 min

Inform participants they will break into teams of two, creating solution-focused designs for a specific wicked problem, grouping unlike elements into unique combinations.

While still in the large group,

  • Participants form teams of two.
  • Presenter: ask each team to select a wicked problem from the list of ill-defined problems.

The list of Ill-Defined Wicked Problems

Participant teams may select the same problem to solve, although it is more interesting if each team selects a unique problem.

  • Homelessness
  • Human Trafficking
  • Drug Addiction
  • Melting Arctic ice
  • Education in 3rd world countries
  • Access to health care
  • Terrorism
  • Poverty

Explain that each team will create solutions for their selected ill-defined problem using an element from either of their lists of favorite things as an appositional cog.

Remind participants of the Designerly way of Thinking approach to problem solving

  • Resolve ill-defined problems
  • Adopt solution focused strategies
  • Employ abductive/productive/appositional thinking
  • Use drawings, images, prototypes, and other modeling media as means of problem solving, with imagery as the primary communication method.

They may choose to eliminate a part of the problem, elevate a solution to the problem, or both.

Share the “Wicked Problems” working space, encouraging teams to add text, images, workflows or other visuals to explain their solutions.

Teams of two activity: 20 min

Start smaller sessions for teams of two. Let them known they have 20 minutes. Periodically share how much time teams have left: 15 min, 10 min, 5 min, 2 min.


3–4 minutes per team

Bring the participants together in the large group. Encourage each team to present their solutions, sharing their selected wicked problem and the element they pulled from their list of favorite things to build an appositional solution.

Celebrate the contributions of workshop participants. Share your contact information if they have questions on the topic.



Diane Bowen

UX Research Manager, motivated to invest in my team, craft exceptional end-to-end user experiences, live with integrity, and contribute joy where I’m planted.