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On the surface, this question seeks to uncover the practices, techniques, behaviors that made previous projects work well. But every client, project stakeholder, and product owner brings their own foibles to a project. As an outside consultant, I try to use the sales process to understand how a person ticks, so when things get hard on the project I know what to expect. But this isn’t always feasible, and so early the project, I want to understand how well the project stakeholders know themselves. That’s at the heart of this question. Not only does the stakeholder know what they like in a vendor (or consultant, or agency, or design partner), but also do they know what constraints they themselves bring to the project. Through this question, I can see how much a stakeholder has reflected on the process and their role in it.
There are two types of people this question is for. Both come with expectations about designers – how they integrate with the team and how they add value. One is the day-to-day participants on a project team. It’s good to understand how they see your role as a designer, but also what kinds of behaviors can keep the team moving forward.
The other is the executive stakeholder who enters the project infrequently, or perhaps is getting updates through the day-to-day project stakeholder. I like asking these folks because even though you don’t interact with them all that often, you get a sense of what left a lasting impression. This also helps you understand how you, the designer, can help the product owner manage up.
Inevitably, everyone says communication. I’m not denynig that good communication is the hallmark of excellent project management. But communication is to project work as oxygen or water is to living creatures. Such an answer, however, opens you up to digging in further, like asking what good communication looks like. Everyone loves communication until there’s too much of it.
This question occasionally turns up useful insights about some members of the team. You’ll find out who struggles to hear constructive feedback, or who feels threatened by the design process.
This is a good question to ask during a kick-off meeting when you’ll have as many people involved in the project. It’s one that works well when you go around the table and ask each person to contribute one thing that worked well. The purpose of a kick-off is to
This question also comes up when you’re at a crossroads or difficult situation. I could see using it when hitting a roadblock with an obstinate stakeholder or teammate. I could see using it when struggling with competing goals or egos. Answers may not offer a way around the situation, but they may help you see things differently.
Kick-off meetings, where this question might make the most sense, lend themselves to so many questions there’s always something interesting to ask next. But if you’re trying to follow on from this one, you can ask for elaboration in their responses, or to tell you what didn’t work on prior engagements. If you really want to dig in, ask them to tell you a story about something that went well (or not well) on the previous project. Encourage them to elaborate on their answers by giving specifics about priori engagements.
When you’ve worked with other teams, what hasn’t worked well?
Last time you worked with us, what worked well?
Last time you did a workshop like this, what worked well?