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005 // The Swiss-Army Lives of How-Might-We Questions

Image with text. Text reads: Ideas from Dawan for people who think and solve like a designer.

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When someone comes to me wrestling with where to start when creating something new, I’m going to ask them the one question to rule them all — “What problem are you trying to solve?” 

We face enormous pressure to solve problems, overcome challenges, and capture opportunities. We want to rush into making things and decisions without pausing to find the problem we need to be solving. Searching for the problem we want to solve feels like slowing down, but it’s how we set up our innovation work to be fast and effective.

I’ve written about how “What problem are you trying to solve?” is behind every innovation action and how to answer that question. In this Ask Like a Designer article, I’m going to dig deep on what to do with your answer. This article focuses on how phrasing the answer well supports healthy thinking about innovation, fuels team collaboration, and focuses change leadership. You’ll see how playing with your answer helps you find magic in the innovation journey mess.



How-might-we questions help us define the fuzzy edges of the problem we are trying to solve. How-might-we questions accomplish a lot, but follow a simple formula. Consider these questions: 1) How might we use existing relationships with hospitals to combat disinformation? 2) How might we destigmatize substance use and harm reduction in the eyes of local political leaders? 3) How might we make mentally healthy practices a natural part of how we learn and teach on campus?

Each of those questions has three necessary parts and two optional parts.

how might we question parts diagram, described in article text

“How might we” prompts searching for possibilities. The catalyzing verb is the doing that matters. In the examples above, “combat,” “destigmatize,” and “make” are the catalyzing verbs. The target noun focuses the problem space on a domain. Substance use and harm reduction are the domains in the second example above.

Adding who we serve can shrink the problem space opened by a how-might-we question. In the third example above, we could replace “… we learn and teach on campus?” with “… transfer students learn on campus?” Sometimes we know what outcome or outcomes people are seeking or need. We could add an outcome for students by phrasing the question this way: “How might we make mentally healthy practices a natural part of how transfer students learn on campus so they feel less isolated?”



How-might-we questions support thinking essential to creating new possibilities and the mindset designers develop over time. If a team describes their problem as “Creating a new Central London hotel,” they will produce very different outcomes than if they were asking, “How might we create a better way to experience short stays in Central London?” The how-might-we question pushes the team into a space with more possibilities.

How-might-we questions also help us change our focus as we learn. The numbers, stories, observations, and experiments — the data — usually suggest better ways to craft the how-might-we question shaping the problem space. Listening to what the world is teaching us about the problem is expressed by tweaking a how-might-we question to reflect what we’re learning. That tweaking is reframing. Reframing our focus as we learn is a dance at the heart of innovation and asking like a designer.



Most teams are made up of high-performing, goal driven professionals. But ask a team working on creating something new what problem they are trying to solve. Ask each person to quietly write down their answer. Next, ask how confident they are that all of the answers will be materially the same. Step back from the table when they reveal their answers. There’s a good chance you’ll get splattered with confusion, dissonance, and maybe a little anger, when people see the chasm between their confidence level and reality.

A how-might-we question helps a team align research, ideation, experimentation, and planning. Each choice will be based on a shared understanding of what the teammates are doing together. If someone starts to diverge from that shared understanding, the how-might-we question serves as a way to have a reframing conversation with the team. The how-might-we question also helps people who work with the team but are not on the team, like subject matter experts, customers, or external partners. 



Some innovation teams have leaders. Some teams consider every member a leader and act accordingly. However leadership is practiced, the team needs to know why a project matters, what the project goal is, and the project’s scope. 

The why is implied by a how-might-we question. It’s in the possibility of an answer. If answering the question feels like it will generate the world we want from the world we have, there’s our why. If it doesn’t, that means it’s time to reframe the question.

The need for clear goals is basic human behavior design. Metrics and revenue can provide goals, but the journey from zero to something needs more fuel. A how-might-we question provides that fuel by giving the team a challenge they can articulate at the beginning of their journey. The question also provides starting activities they are capable of performing — the investigation and sense making they’ve used over a lifetime of answering novel questions.

A how-might-we question makes it easier to see the edges of the problem space, the blurry line where one problem ends and another begins. Team leaders can pause to talk about the problem framing when the team starts pushing into territory that seems like it might yield a valuable answer to a different question. A how-might-we question becomes a way to have conversations about project scope.



Guide. Adviser. Judge. Using a how-might-we question to represent the problem space in an innovation project provides several kinds of support on your innovation journey. As a guide, it constantly reminds you where you are and what you should be doing. As an adviser, the question helps you see when you are nearing the edges of your problem space and gives you a concrete way to choose whether and how you change that space. As a judge, a how-might-we question helps you make decisions about research, ideas, experiments, and plans. 

There’s no magic to using how-might-we questions as part of your innovation process. Your hard work just feels like magic as one question does so much for you, your team, and the outcomes you desire.

How can you play with how-might-we questions? Start by thinking about the world you have and the problem, opportunity or challenge you’re grappling with. Now, imagine the better world a good solution might create. Focus on the better world, not a solution. A solution is just one answer to a how-might-we question. We want the question that opens the possibility of many workable solutions during our design process. That is, questions that, if answered, bridge the gap between the world you have and the world you want.

Next, look for your how-might-we question by creating many questions that might work. Once you have many questions, choose one using this test, “If we answer this question, will we have solved our problem?” 

I’ve created an Ask Like a Designer Thinking Tool you can download here. Enjoy.

The Swiss-Army Lives of How-Might-We Questions

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