5 Key Takeaways I Learned From Leading a Design Thinking Engagement

Jordan Kolb
4 min readJun 14, 2023


At my most recent job, I had the opportunity to lead a design thinking engagement for a multi-billion dollar enterprise client. It was an incredibly educating experience and the skills I gained helped me so much throughout my career. Here’s hoping it will help yours, too! Let’s just jump into it! These are 5 takeaways that I keep in mind for future client engagements!

1. Prepare to Adapt Your Process

As a UX Designer, having a defined design process (like the double diamond) ready to explain to those unfamiliar with design thinking is helpful in evangelizing that what we do can be extremely valuable to them.

How the ideal design thinking engagement would go…

However, there will be times where clients have their own teams to do their own research. In those circumstances, it’s up to the UX Designer to adapt the client’s process into their own. Sometimes you will need to pivot based on information gained from the design thinking workshop. It’s helpful to create a schedule to share with the client so that they are confident you are applying their research to your workflow. Understand that your process will be a lot less linear than you might initially believe.

What actually happened

2. Have an Agenda

Have a plan going into design thinking to ease the client into your workflow and ensure they understand why we are going through the process. Here is an example of the Design Thinking

Agenda we used for this engagement:

● Schedule a design thinking 101 session a few weeks prior to the start of the engagement

● Plan to review the what and why we do design thinking. Then, explain how we will accomplish it.

● Ensure the client knows both sides will be collaborating together. They will need to be responsible for identifying their core team and list of end users for usability testing.

● Review the source of truth that the client will have access to throughout design thinking. IT should provide timelines, a decision log, links to resources and more. Having an easily accessible source of truth ensures both parties are following the same agenda. If that agenda needs to be adjusted, everyone is aligned on the changes being made.

3. Be Prepared to Meet Your Customers Where They’re At

Take the schedule you created and be mentally prepared that it isn’t final. Situations may occur that require time adjustments. It’s important to keep both the client team and internal team notified of any changes, especially if the internal team is handling the budget. Letting the client know you are in control of the schedule inspires confidence in them. Sometimes, you will be facilitating a design thinking workshop and information critical to the success of the project doesn’t come to light. Sometimes, topics that you originally assumed the client team was in alignment on require more time than anticipated. Situations like these can break fine-crafted schedules and require additional puzzle-piece meetings to fix. Being fully transparent with your expectations from the client is important so there are no surprises down the line.

4. Your UX Skills Are Your Toolbox

I found myself taking bits and pieces of the Design Thinking process I was familiar with and applying the most relevant ones to gather the information we needed. During our initial design thinking workshop with the client, we learned we needed to pivot. Since our assumed scope was adjusted, we needed additional context to understand the features we would be designing for them. I requested to see a run-through of the existing application. I also scheduled meetings to ensure we could spend time narrowing down the scope and prioritizing features for this minimum viable product.

A UX Designer should be able to pick and choose what we need to do the job properly. Spending time experimenting with the tools in your kit will help you gain experiences on which strategies work best and when.

5. Stay Organized and Know Your Core Team

It’s important to determine roles and responsibilities early. The more aligned everyone is with the work that needs to be done, the smoother the project will go. This requires a surprising amount of communication both internally and with the client. I found myself asking questions, sculpting the schedule, organizing meetings, and keeping teams up to date as much as I was designing and making presentations. Active listening and staying organized are skills that really help here. So much of the necessary information you will need to understand the project is received from direct talks with the client. Make sure you are taking notes during every talk with the client and send follow up communications outlining key takeaways to ensure there are no surprises.

Reiterating what you’ve heard is important to ensure your team and your client are aligned.

As I wrote this article, I found myself unable to keep this list to just 5 pieces of advice! If you want more, here are 5 more takeaways that I’ve learned throughout the past year! I hope these pieces of advice help shape you to become a better UX Designer as they did for me!