Stakeholder interviews: asking the right questions

Over the last few months, I've been doing less designing and more... talking. Except, talking isn't quite right because, in order to do my work correctly, it's the opposite of talking - it's listening. You see, in order to design the right thing - in the right way - you'll need input and you need to understand the problem that you're solving. Even when working with interior designers from Herman Miller, they are continually starting over in analyzing what problem the client is experiencing. Without that full insight, their solution is nothing more than a guess. So, for the past few weeks I've been helping my two major clients, Herman Miller and Eneo, by facilitating stakeholder interviews to get those answers.

It's not users vs. business, it's users and business

The way I usually tend to run interviews is through the lens of the two parties - users and the business. While I'm always looking to create things that will benefit the end-user, it's important to remember that the business also has goals that need to be fulfilled. It's only when you, as a designer, understand that you have to work to fulfill both parties' goals and expectations, that you can succeed.

Facilitating a conversation

One of the first things I tend to do during interviews is to explain my process and agenda for the next hour. Most people haven't been in a stakeholder interview before so it's natural that they are unsure of what to expect. The key is to make them feel as relaxed as possible. What I usually begin to explain is the reason why we are doing interviews. That our goal is that we want to understand the reason behind the project. In order for the project to be successful, we need to tap into all their experience and knowledge. We need to make sure that we have a cohesive vision of what it is that we're supposed to create. I explain that I ask questions from both sides of the coin - the user and the business. Finally, I tell them that I'll be recording the interview in order for me to be able to revisit it later and not be distracted by having to take notes.

Starting small

I'll usually begin with a simple question that they easily can relate to. For instance, I'll ask what their role is and how they became involved in this project. This allows them to begin talking more freely and it's a great opportunity to shift the "talking part" from me to them.

As I move to asking questions about the business, I want to talk more about what the short and long-term goals of the projects are. I need to know how they would define a successful outcome as well as what would happen if this project isn't done. One of my favorite answers to the last question came from a South American who simply stated, "Well you know, life goes on..." It sure does :)

I'll also try to understand the motivation behind the project. For instance, what do you currently have too little of (sales, profits, customers, etc.) or too much of (complaints, product returns, service calls, etc.)? This gives me an idea of what some of the outcomes could be and positions me to start thinking of additional solutions.

Once we're talking about what some of the potential solutions could be, I'll ask about how they would describe their users (or customers). I'll try to put them in the minds of the user and ask about what steps they would go through before making a purchasing decision. In order to understand the big picture better, I'll ask what they think the single most important message or feeling that a user should remember from the product is. This focuses on the pain that we're trying to solve instead of a deliverable.

As final questions, I like to ask them for one thing that they believe no one else from their team has mentioned. You can find some really great insights in these responses!

Here are some of my questions that I use:


  • How did your organization or team get to where you are today?

  • What are the short- and long-term business goals?

  • What would a successful outcome of this project look like to you?

  • How is your organization experiencing the problems?

  • What do you currently have too little of (sales, profits, customers, etc.), or too much of (complaints, product returns, service calls, etc.)?

  • What should this project accomplish for the business?

  • What happens if this project is not done?


  • Who are the users? How would you describe your customers?

  • How do they currently think or feel about your industry as a whole?

  • What steps do they go through before making a buying decision?

  • What are some surprising insights you’ve gained from working with these customers?

  • What problems do customers currently have that this offering solves?


  • What are a few product concerns?

  • What’s missing in the current process that this tool will provide?

  • What is the single most important message your audience should remember from this deliverable?

  • What action should this deliverable entice the user to take?

  • If users had a “magic wand” and could wish for anything to make the process better, what would they wish for?


  • What do I need to know that you don’t think other members of your team have said?

  • Is there anyone else, in particular, you think we would benefit from interviewing? Who?

The real insights are not in these answers

While the above questions and their answers are valuable, that's not where the real insights lie. You see, the real insights are hidden in the follow-up questions and answers. The key to a good interview is to listen carefully and follow-up with questions that go deeper. With all questions, it's important to keep them as open-ended. This helps to make sure the discussion stays as open as possible. The method I like to follow is TEDW ("Tell me about.. Explain.. Describe.. Walk me through"). These offer the other person the option to not just answer, but paint the whole picture.

As for facilitating, the key is to stay positive and engaged. This is something that I find the hardest! When you're on that third hour of Zoom calls, it's so easy to get distracted or just quickly check your email. The truth is that the other person will only stay engaged as long as you do. As soon as they can tell that you're not paying attention - in fact, as soon as they'll even expect that you're not paying attention - they'll lose focus themselves.

Finally, always stay curious. It's not uncommon for people to start brainstorming solutions. Even if they start pitching something that you know probably won't work (or would cost trillions of dollars to build), it's important to stay open. "Wow! Explain to me how you think that could work!" and let them go for it! Having a candidate that's thinking freely and creatively is exactly where you want to be.


I like recording my sessions so I can rewatch them later and make notes. On some projects, like with Herman Miller, I had the luxury of having a team listening in on calls and taking notes so I can just review their notes afterward, but often that's not the case.

What I want to do is revisit all of the interviews a couple of days later and see if the same themes still stand out to me. Often they do, but often I also find variations of that theme because of what someone else mentioned on a later call! It's the pieces of all of the interviews that will eventually solve the puzzle.


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Join thousands of designers, developers, and product people from companies like Amazon, IDEO, Figma, and Shopify on my mailing list. Usually once or twice a month.

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