Questions as a Superpower: The Underrated Skill That Unlocks Better Solutions
Great design isn't just about having answers—it's about asking questions that matter
Last month, I shared my musings on how creative habits differentiate good designers from great ones. I want to share another indicator I’ve identified over the years: asking questions. Not just asking them for the sake of it, but being completely intentional about their purpose.
I’ve seen firsthand how a room full of curious minds can elevate a fireside chat to a memorable moment that leaves you full of insights and motivation afterward. On the other hand, a project kick-off with poor questions or no questions at all can easily leave the wrong impression of a disengaged designer despite their good intentions.
To me, this is an underrated skill for not just any designer but anyone involved in building products. Let’s explore how we can level up our game of asking better questions exactly when needed.
Questions as Turning Points
Have you ever played “Guess Who”? I loved that game as a kid. For those unfamiliar with it, you and another player each have a board with 48 face cards, and a randomly selected face card in front of you. Each player will try to guess the other player’s face by asking questions about their appearance, eliminating suspects until one of you makes a correct guess. The key to the entire game is to get the most essential information and make an educated guess with the least amount of questions. That sounds oddly familiar to work-related meetings.
"If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes."
— Albert Einstein
It’s easy to just go through the motions and forget how easily a question can impact a conversation, so I decided to make a list. It could be even longer, but you get the gist. These are some situations in which great questions can be incredibly valuable:
Interviews, both as an applicant and as a hiring manager
Design critiques with your team
Design reviews with stakeholders
User interviews with users of your product
1:1s, both as a manager and as a direct report
Negotiations with potential customers
Discovery calls with a client
and the list goes on...
If questions are so important, why do we take the backseat and avoid stepping up to make thoughtful and nuanced questions? It can be a matter of shyness, lack of experience, or just not knowing how to ask things in the first place. Regardless of the reason, the best approach I’ve seen in practice is simple: Plan ahead of time and listen carefully.
Curiosity as Method, Not Just Mindset
Why is the sky blue? Can we travel to the sun? What’s in the depths of the sea?
These are all kinds of questions any curious kid would ask. I still have them, and look for answers almost instantly because I want to understand genuinely. Asking questions professionally is not too far from that, at least not for me. You want to understand something, pose a big question, and pay close attention to the answer.
It looks something like this:
Learning goal → Key questions → Use active listening
Learning goal
I like to start, first and foremost, with what I want to learn; everything else should follow suit. This can be the main problem: what the other person cares about the most, or how that team defines success. Clarifying the end will prevent you from asking unnecessary questions or going down the wrong path.Key questions
This is the part where you share the big questions that hopefully get you the answers to learn. Make no mistake, I’m not talking about big existential questions that will prevent people from sleeping later that day. Sometimes, asking “Why is this important?” or “How could this go wrong?” will get you further. The nuance behind the answers will yield the most results, not the ones that give you predictable answers, so aim for open questions, not leading ones.Active listening
This, to me, is the hardest part, and I’m sure many can relate. The point of asking better questions is to get the best insights, but it’s always tempting to keep thinking of the following question on the script and fall into the trap of listening without paying attention. Instead, focus on genuinely understanding what the other person is sharing, which can get you to unexpected insights, unscripted questions, and diving deeper.
If these steps sound familiar, it's because I’m borrowing from user research’s playbook. During a Dive Club episode, Noam Segal, Head of UX Research at Zapier, explained how, during an interview, the person conducting the interview tends to follow a script blindly instead of paying attention and allowing the conversation to flow naturally to find unscripted follow-up questions that would uncover much more valuable insights.
"If I ask you a question, I don’t want to listen to have any reaction when you’re speaking. I’m trying to be as neutral as possible. My goal is not to form an opinion, is to understand”
— Rick Rubin
Crafting High-Value Questions
Before diving into this topic, my first instinct was to say it depends. It truly does; it depends on the context, airtime, audience, and so much more. Regardless of the highly nuanced nature of when and where this is happening, I’m also systematic. When I found this talk from Chris Do on this topic, I knew it would provide me with answers.
In the talk, Chris shared a practical framework that he uses to create better questions. It's called the “Pro-ACT” framework and comes from Jason Barron's book The Visual MBA.
What is the problem? Understand the real challenge
Have a clear objective: Define clear goals
What are the alternatives? Consider multiple options
Consequences of each alternative: Evaluate the impact
What are the tradeoffs? What does saying yes/no mean
What I like most about this framework is its flexibility, without necessarily making binary rules about the structure. Each point of this list can be a series of questions and be phrased slightly differently depending on the conversation, but once again, the idea is not to treat them as a script to follow or a checklist to go through. The ultimate goal remains: Learn, understand, and gain clarity to move forward.
Your Question Toolkit
About 8 years ago, my game plan was straightforward before I had conversations with stakeholders. Before the first meeting with a client, I would ask the PM for a background overview. This would give me ideas of key pieces of context I wanted to understand, which would materialize as a loose question list for the meeting. Only years later, reflecting on my process, I understood why I did this: I needed to leave that meeting with a clear path for actions. I needed clarity.
Over time, I developed a different approach, going for quality over quantity to ask the least amount of questions while also getting the highest amount of insights. In some cases, you could even make just one question, but if it’s a question that leads to deeper understanding and clarity, I can assure you it’s a win-win all around. You'll leave the conversation feeling confident about what happens next, a natural eagerness to see what happens next that reminds me of a child’s questions and the rabbit hole they usually open up. Better questions will get you the confidence to take the right next step.
During this time, I found tricks to prepare better questions. Banks of questions like this one are easy to start, but now I prefer to “steal” great questions from experts in their field, taking note and keeping them in my pocket for the next time I’m in a similar conversation where it fits the purpose. Here are a few sources I’ve saved over the years:
Discovery questions with a prospective client, by Dan Mall — Perfect to encourage prospective clients to talk about the future
Business questions during a design project, by Alen Faljic — Strategic prompts that connect design decisions to business outcomes
Questions to develop rigorous thinking, by Wes Kao — Thought-provoking questions to challenge assumptions and push past surface-level analysis
Career reflection questions, by Julie Zhuo — To guide introspection about your career path when you're feeling stuck or considering your next move
High-signal-to-noise interview questions, by guests on Lenny’s Newsletter — Battle-tested questions from industry leaders, whether you're interviewing users or potential team members
Look at them and grab the ones that fit your most immediate conversation. None of them is a one-size-fits-all, but they can become powerful tools in your arsenal if used properly. It takes time to come up with your questions, especially when you’re just starting, but I’ve found that analyzing and trying out the questions others have shared has helped me develop critical thinking about making the right questions at the right time.
Parting thoughts
You can tell a lot about a person based on their questions. Are they asking obvious binary questions, or do they make you pause and reflect? Are they going for the safe questions, or does it help to uncover valuable insights? Are they going on tangent, or does it move the conversation forward? It seems obvious when someone is good at that, yet it’s hard to describe most of the time.
Each section of this article could become an article of its own. What started as an introspective moment of trying to understand why questions matter in the first place was a deeper discussion on any avenue I wanted to go, but I wasn’t going for that here. Instead, I tried to treat it as a pause on a topic we rarely discuss, reflect, and remix some of these ideas to make them your own.
Regardless of where you are in your career, improving your questions will be an invaluable skill wherever you go. It has certainly helped me a lot and allowed me to be in conversations where it wasn’t common to see a designer. Everyone knew it would help others as well, even if I wasn’t the one talking the majority of the time. I hope these learnings are helpful for you or someone you know, so you can start improving your question game as soon as today.
Before your next meeting, write down three questions that focus on learning rather than confirming what you already believe. Notice how responses to these questions shape your understanding differently. So tell me, what are your favorite questions?
Learning shortcuts
Tools and tactics for modern user research, Dive Club interview with Noam Segal
The Art of Asking the Right Question, by Caroline Reidy
Rick Rubin’s approach with artists, on the Lex Fridman Podcast
The introvert’s guide of how to sell without being to selsy, a Twitter space by Chris Do
It's always more fun to learn with others than doing it alone, so don't hesitate to reach out on Twitter or Bluesky if you want to continue the conversation. If this article has been helpful, share it with a friend!
Over and out,
Laura ✌️