How to Actually use “How Might We…?” Questions

Those of us who are familiar with design thinking are familiar with IDEO. These guys are the godfathers of interesting facilitation techniques that stimulate diverse groups of people to solve problems and come up with solutions.

So the story goes, the first thing IDEO does when they tackle a new design challenge is to begin with the question “How Might We…?” and then generate responses from there.

The technical term for their approach is “Challenge Mapping.”

But every time I’ve heard of this approach, I’ve wondered if there was more to this than just the HMW question. What does Challenge Mapping actually look like in practice? How do you do it?

I’ll show you how:

What is it?

Challenge mapping is a collaborative problem framing and refining method that generates many alternative strategies and tactics for tackling a problem.

Why should I use it?

Because a question is better at priming the collective intelligence of a group than a problem statement. Challenge mapping re-frames your problem in a way that invites others to think on it and take action. It helps you make distinctions between both the strategic and tactical approaches you can take to solving a problem. And it offers you an easy way to refine the problem you are trying to solve through a few iterations.

The Origins of How Might We…How three words made design better.

How does it work?

I really like Charles Warren’s description of how to Challenge Map in the video above. Having done it a few times, I can say that it’s not as easy to do as you think, and Charles is really only giving a high-level introduction to it. So, for this week’s tool I’ve tried to distill the exact step-by-step process for running this type of design thinking process.

Depending on the group size, either facilitate the exercise yourself, or create breakout groups, giving the groups the basic instructions to self-facilitate the exercise (if you do multiple groups, you can have folks report out while you draw up a master diagram from the collective input).

Start out by dividing up a wall/chalkboard/whiteboard/sheet of paper/etc. Have a look at the diagram I posted on Insta a few months ago for help:

Come up with different ways of describing “the problem” or the challenge:

  1. Translate your problem statement into a “How might we…” (HMW) question (i.e.: instead of “Our community is too insular.” write: “How might we better connect neighbors with one another?”).
  2. Do this a bunch of times and come up with different HMWs! (“HMW encourage neighbors to talk with one another?” “HMW get families in the community sharing babysitting resources?” Etc.).

Generate strategies:

  1. For each of your HMWs ask the perennial preschooler question “Why?” and if unsatisfied, continue asking “Why?” (just like a preschooler).
  2. Write the answers the group gives on post-it notes and post ’em above your HMW question.
  3. After you’re done, you can organize the post-its in ascending order from least abstract to most abstract (to take our neighborhood example further, we might answer “To help people in the neighborhood have a feeling of safety and security.” If we want to go deeper, we can follow that up with another “Why?” and answer “To do our part in promoting a welcoming city.” and so on).

Generate tactics:

  1. Have a look at your HMW problem statement and ask “What’s stopping us?” (“What’s stopping us from connecting with one another?”) and write the answers that the group gives on post-it notes and post ’em below your HMW question.
  2. After you’re done with this part, you can organize the post-its in descending order from the least detail to the most (to continue with the example, we might answer “too many cars on the roads” and so on).

When facilitating a challenge mapping exercise, consider the following:

  1. Before the event: really think through how you will explain it to the group. Come up with a really easy example of a HMW question, so folks can grasp the exercise easily.
  2. In the beginning: explain to the group what it is, why you’re using it, and how it will work (obvs!).
  3. During: moving up in the diagram leads to greater strategic abstraction and moving down in the diagram leads to more tactical detail. The things that are standing in your way are elements of any future project or program you develop to tackle the problem.

If people look stuck, check-in, make sure they understand the exercise and help them with probing questions.

If folks are having trouble coming up with more HMWs, do one HMW and then look at the post-it note answers in the “Why?” section. Is there anything in there that better captures the essence of the problem you are trying to tackle? Is there a better way to frame another HMW question buried in the post-its? If so, create a new challenge map with the better HMW question as your starting point.

What resources do I need?

A few hours. A facilitator, or self-facilitation. A meeting room (and additional rooms if the group is large. Post-it notes, markers, masking tape if using a wall (to divide the sections), if no wall, large format paper, whiteboard, chalkboard, etc. Recording equipment is optional (camera, video, audio).


Lastly, I’d love to hear from you in the comments if you’ve tried this quick little recipe out. Was it successful? What did you learn by doing? What would you change about the approach?