How to facilitate a design thinking workshop for digital transformation

This article is taken from a module of our design thinking facilitator train-the-trainer program which we run digitally.


Digital transformation is a significant and common challenge for organizations and thus a great design thinking project. The year 2020 forced organizations across disciplines and industries to digitally transform. Leaders, facilitators and design thinking project leaders also have to be creative about working virtually. There are current tech opportunities to seize when you’re working on the challenge of design thinking digital transformation. You can do a lot to help an organization, teams, or individuals in the larger project and especially in the time-bound workshop where you make digital transformation the “case-in-point” while you are leading or facilitating.

How to navigate from onsite to digitally transformed virtual workshops

Some people may want to go with the status quo and the old way of conducting design thinking workshops such as post-it notes on the wall or people in person together. However, can we digitally transform how we do that too? That’s the key that I like to address in the workshops. 

Let’s do it remotely; let’s do it virtually. Let’s use some of these tools and techniques to show them what they can use in their own work, and digitally transform how they manage their day-to-day workload.

This could be a good design thinking challenge to work on if you’ve got a general audience addressing how people can digitally transform work as a leader or the projects that they work on.  

Using whiteboard virtual tools

You can use real-time whiteboarding tools like Mural or a loom video to host and facilitate these virtual workshops. We have personally used these tools during COVID-19 and beyond to continue to facilitate and educate others on design thinking and innovation methodology. 

By showing them the things we’re using to digitally transform and how we’re doing it in the moment, we can inspire your team to face their own challenge too. They’ll get to work on that challenge directly and transform how they’re working. 

Using design thinking books as digital transformation tools

For other more detailed avenues related to the organization or other directions within the organization, we recommend the incredibly popular book The Design Thinking Playbook. It also shows workshop activities/formats:

This book really stands out because right there in the title, “mindful digital transformation” is in the first line. This book is going to get at design thinking for the purpose of digital transformation. So if you want to go really deep, you can pick up this book. For audio-centric listeners, it’s also available on Kindle right now. 

Utilizing e-books on Kindle and activity guides

Kindle is also digitally transforming the way of reading a book. They’ve got a whole section on how to kickstart digital transformation with different sections in the book and examples. You can see all kinds of design thinking, activities, workshops or models that you could do for that case. There is also a workshop laid out in a two day format. Kindle, along with the Design Thinking Playbook, and a workshop designed around the participants, can help you understand how to digitally transform what you do.

The challenge here with a lot of the projects in the design thinking world is that there’s a lot of activities and you’ll want to learn (or do) them all versus focusing on getting started with the critical few. Another book called the Design Thinking Toolbox focuses on nearly 100 different design thinking activities, tools, and techniques to do or use in a project. This can seem overwhelming, especially for new design thinkers! However, rest assured that you don’t need to learn all 100 activities to make a difference with a digital transformation design thinking project. 

Using guided idea generation

For a workshop you may not have that much time. Whether it’s an hour and a half session, or several days comprising of three hour sessions, you need to be able to quickly grasp the key concepts and move on. You can get to the essence of digital transformation by guiding the audience through an idea and letting them do the empathy work to find out how they can help their customers or their users with a digital solution.

Using “How might we?” questions

You can zero in on that with a “How might we?” question or statement and then turn that into a workshop where you might do some idea generating and prototyping.

Design Thinking Digital Transformation Conclusion

This loom video and article shares some quick thoughts on the concept of digital transformation for design thinking workshops and what you might design and facilitate. Most important, digitally transform yourself and show your audience. Be their guide to do so themselves too.

Also see our transformation training and transformation workshop posts.