5 *More* Takeaways I Learned from Leading A Design Thinking Engagement

Jordan Kolb
4 min readAug 1, 2023


Previously, I wrote an article detailing the takeaways that have helped me throughout the future design thinking engagements I‘ve taken part in. I discussed how important it is to have a thorough agenda prepared but be ready to adapt your process and go into the workshop meeting your clients where they’re at. Sometimes you will need to take pieces of your team’s established design thinking process and throw them into the agenda when needed. Lastly, go into the engagement knowing half the work is going to be maintaining consistent communication with the core team and client. Building off of these points, here are 5 more takeaways that have helped me throughout my career:

1. Be Thorough and Don’t Be Afraid to Ask Tough Questions

Long-term projects are like a pyramid. The larger and better-structured the base, the easier it is to build the layers on top and the design thinking process is often at the beginning of the development cycle. Needing to spend extra time facilitating talks about scope prevented me from knowing when to stop a potentially derailing conversation or a discussion that was going around in circles.

I made sure to schedule talks with the client after the workshop to gain the necessary information we missed. This included two walkthroughs of their current system from both a design (desirability) and backend (feasibility) perspective, a meeting to ensure we understand the areas of their problem, and a meeting to lock in the project’s scope. This allowed us to quickly get back on track with only a minor delay.

Identifying that core group of people to regularly communicate with early will help with decision making and expedite getting the information you need to design successfully. Understand what needs to be understood… and if you don’t understand what needs to be understood, talk to the client core team to gain that understanding!

My favorite analogy to describe why we spend time properly doing design thinking.

2. Gain Your Clients’ Trust

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. Making a schedule is not only great for client confidence, but for time-boxing as well. Providing weekly updates proves you have a game plan, sharing notes proves you have been listening to what they have to say, providing consistent updates to the team shows that work is being done, and reiterating topics of conversation demonstrates you are listening.

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. To reiterate a point from my previous article: 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! Even if you don’t feel confident in your own skills, doing these things will provide visibility of your efforts and gain your clients’ trust.

3. Be Thorough During Discovery

Collaborating with a UX Architect who worked with this client before helped me to gain a basic understanding of the client’s system. Having scheduled meetings to see a firsthand run-through of the screens our end user is interacting with set us on the path to consistency with their existing layouts. Not only do you want to adapt their design system, but you also want to keep your layouts consistent with what users are already used to. Keeping this in mind will make your usability tests run much smoother and gather feedback that is sure to impress your client.

4. Collaborate With Your Team to Know What’s Feasible

Having a balanced team can provide you with perspectives you would not have normally considered when designing. The UX Architect I collaborated with had plenty of development experience and understood the limitations of the technology the client was using. I took advantage of this by frequently sharing my work with them and gauging the feasibility of certain features from a development perspective. Like I said earlier, projects like this are built like a pyramid. The more effort put into a solid foundation, the easier it is to build the layers. Putting in the effort during the hi-fidelity design phase means less time spent correcting work in the future.

5. Review Your Works in Progress With the Client

As nerve-wracking as it is to have people seeing your unfinished work, it really is beneficial to have clients see designs early. If there was a miscommunication or if the design is heading in the wrong direction, it’s better to get that out of the way as soon as possible. You don’t need to share your preliminary sketches or low-fi designs with the entire client team, just the most relevant core group.

These 5 (now 10 in total!) takeaways are going to be staying with me as I continue to gain more design thinking experience. What initially seemed like a difficult situation turned out to be a rewarding and highly educational experience! Leading this engagement last year gave me the confidence and skills to grow as a UX Designer. I hope these takeaways help you in your UX career as well.