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The “this” in this question almost always refers to a collaborative design activity, especially one in which participants who are not designers have to exercise their brains. Design activities may be fun, but they’re not easy. Even if you have a good idea, representing that idea in a way that’s accessible to others can tax your creative energy. Through this question I’m asking participants to reveal the parts of the exercise that got them to think the hardest. Perhaps these are dilemmas they faced in sketching a screen design or in sorting content into categories. They might be unanswered questions about the requirements, or lack of clarity in the exact design problem. By asking “what made this activity hard?” I’m asking them to highlight the most challenging aspects of the project in front of us.
This question is directed at workshop participants. Usually these are teammates from the core team, but often includes folks from the extended team, too. By extended team, I mean people who have an interest in our project but are not involved in the day to day business of it. The extended team is generally aware of the project and our efforts. They generally have visibility into the fruit of our work, but don’t always stay up to date with what’s going on. Asking the extended team this question gives you (and the rest of the core team) some insights about what’s top-of-mind for them. It offers some insight into the pressures they contend with, and the forces at play in their particular role and position.
The people who participate in these activities and who have to answer this question are people with a strong interest in the outcome of the design process. But they have little understanding of the process itself. Their answers to what made this activity hard gives me a hook to make the larger point: the design process is about juggling myriad inputs and competing priorities. It’s a process of reconciliation as much as it is a process of imagination. This question is, in part, meant to cultivate an appreciation for this part of the process.
Amidst all the complaints that they ran out of time, you’ll hear an insight or two that allows you to illustrate the larger issues facing the design project. “I wasn’t really sure what the user wanted” can translate into, “We need more insights from real users.” An admission like, “I’m too familiar with how it works under the hood” gives you the opportunity to say, “We’re constrained by existing technology framework.” Expect insights about the team, yes, but also expect to use their observations as springboards to dive into broader points about the project itself.
I don’t use this question after every workshop or collaborative activity. I save it for the activities that I know are going to be cognitively taxing, perhaps because they demand participants put themselves in someone else’s shoes. This question is appropriate following activities that take people out of their comfort zone, that compel them to use their imaginations, that ask them to look at the domain in a new way. This question also gives participants a chance to decompress, to relieve some of the pressure that came from doing something difficult. It is a reflexive moment.
You’ve just asked them to do something that might not come easily to them, and then you’ve asked them in a more-or-less public space to reveal what made it hard. This vulnerability creates intimacy, not to mention provides excellent input into the design process. No need to ask them anything further. But what I like to do is reflect back to them what I heard, and then confirm that I understood their challenge.
What made this uncomfortable?
If you don’t want to frame the activity as hard or difficult you can instead acknowledge that it might make some people uncomfortable. In a sense this brings the responsibility back to you, the facilitator, by asking people to participate in an activity that might make them uncomfortable. I might even lead this question with a preamble like, “I know this put you in an uncomfortable place.”
How did you deal with the [challenge]?
You can frame this in a more leading way, anticipating the aspect of the work that they found challenging – perhaps the assignment was purposely vague or they didn’t have enough insights about the users. By acknowledging this in your question, you’re granting permission for them to admit they found the task hard. They might disagree, highlighting a different aspect they found challenging.