How might we write better How Might Wes?

One of the best product design weapons is often the worst abused.


The practice of writing open-ended How Might We (HMW) questions to spark better ideas is nothing new.

How Might Wes can work great. However, there’s a yawning chasm between the best crafted HMW questions and “common or garden HMWs”. You might recognise the type. They sound a bit like this: “How might we redesign our website?” or “How might we make our app more fun?”

Really? How’s anyone supposed to get inspired by such a wooly HMW?

Boring, generic HMWs are just as bad as not having an articulated goal at all, in my view.

An unimaginative or vague HMW can send a design sprint off in a totally wrong direction, wasting valuable designer and engineering time.

Let me be clear: you don’t need to be a great writer to craft an excellent How Might We. You just need to think about it a bit.

Stanford’s d.school has a few excellent refinements to think about when penning a HMW, including “going after adjectives” and “changing a status quo”. I’d encourage you to have a read of that short method card because it packs a lot of punch for so few words. As such, I won’t borrow any more of them here.

Instead, I’m going to suggest another technique that can result in a better HMW: randomly combine user needs, business drivers, and market opportunities into a single HMW statement.

What?? Random? I hear you say. That sounds risky. Suspend your cynicism for a minute. A little randomness often leads to creative breakthroughs.

I find it best to use this in a workshop setting. You will need:

  • At least one team member from each discipline involved in creating the end product. In a digital business, that might be a UX designer, technologist, a salesperson or marketer. And don’t forget the product manager.
  • At least an hour and a half.
  • Stickies and Sharpies and a big enough whiteboard or flipchart to house around 50–70 stickies.

Make sure that there’s some seniority in the team, but not so senior that everyone is simply nodding to the beat of the HiPPO’s drum. It’s a small workshop, so try to get people involved who aren’t afraid to speak up. All sides of the user, business and market landscape need to be expressed.

Caveat: The people in the room should have a solid understanding of the user needs, business drivers and commercial opportunities. And they should have data to back up their assertions. If they don’t — don’t proceed. Go back and get the data to be better informed.

I’m biased, but I have found product managers often make good facilitators for the discussion, as they’re usually able to balance the concerns of the user, the business and the market. Hire one today!

Set aside at least an hour and a half for the workshop. The first part of the workshop — which can be anywhere from 20 minutes to an hour — is called “Bring out your dead”. The second, “Stitch up”, takes around 30 minutes, or a bit longer if you have perfectionists in the team.

“Bring out your dead” asks the team to list 10–15 business problems you’re most keen to tackle, 10–15 user needs or frustrations that you’d most like to meet or fix, and 10–15 interesting market or company opportunities or insights you’d like to take advantage of.

If you want to rank the items in each column in order of priority, go for it. But it’s not essential. All of these issues should be important enough to warrant a future design sprint.

Tip: If there’s enough people participating, split into 3 groups, if there’s representation from all disciplines in each group. Give each group one area to flesh out. Then regroup with the others and present back.

Here’s a sketch of what your output might look like after the first session (trimmed to just a few items per category). I’ve used a (simplified) imaginary content website or app for my example.

OK, so now you’ve got a list of Important Things. Time to stitch them together into tidy, top-drawer HMWs. To instigate a bit of left field thinking, force yourselves to play Countdown with your lists. Take one from the bottom, and a couple from the bottom. Or the reverse. The point is, mix it up.

Draw different colour circles around the three (or more) items you’ve selected for each HMW. In our example, we might end up with something that looks like this:

You’ve got all the ingredients there for a good HMW. Now the task is simple. Try to squeeze a reference to all three circled Important Things into a single, HMW.

Don’t settle on your first draft!

Undoubtedly, the first attempt at your How Might We will be either boring, confusing, or both. So for each proposed HMW, revise it and boil it down (perhaps using the d.school methods linked above) until it’s nicely polished.

Here’s how I winnowed down the red group from the example above.

Iteration 1: How might we create something exclusive for registered users that gets new visitors to experience more of the product on their first visit?

Clearly, this is boring, obvious, long-winded and slightly confusing. Let’s try some compression, and expression.

Iteration 2: How might we tempt new users to sign up by giving them something special that’s theirs to keep?

Getting better, but still lacking impact. Plus, we now don’t mention the opportunity.

Iteration 3: How might we make new visitors feel like they’ve just been given keys to a vast realm worth exploring?

This time, I use an analogy, but also try to reference the opportunity with ‘vast’ and ‘worth exploring’. Problem now is that we’ve ignored the business driver to generate sign ups. Exclusivity’s not shining through either.

Iteration 4: How might we make our sign up process feel like newcomers will get the keys to their own unexplored realm?

OK, so we’ve developed the idea of incentivising sign up as well as the exclusivity and broad first visit. But this can be tightened further.

Final version: How might we help newcomers feel that by signing up, they’ll get keys to a vast realm worth exploring?

Here, I aim to make it a bit more active-sounding.

Within a few minutes, we (hopefully) got to a HMW which combined important business and user problems to solve and addressed an opportunity.

See how many quality HMWs you can generate from your lists in 30 minutes.

Final caveat

This isn’t an exact science. And your mileage may vary. Sometimes, the combinations just don’t work, and you should just focus on a particular user need, or business driver.

But a lot of times, forcing these combinations produces questions that poke into areas you might not have explored in the past.

Plus, everyone reading the HMW will get a little glimpse (hopefully) into all three of the aspects which inform priority.

Give the process a try, and let me know how you get on in a response.