Questions That Unlock Great Ideas

Mar 26

How often have you sat in a brainstorming session that goes absolutely nowhere? People throwing out random ideas that don't stick. Conversations veering off in twelve different directions. The time feels wasted.

We’ve all been there, and it’s easy to blame “brainstorming” as the problem. But the problem isn’t a brainstorm; it’s the question you’re asking (or not asking).

The Magic of a Well-Framed Question

Every brainstorm session needs something to brainstorm against. A great question creates the sandbox where you can build your castle. Without good boundaries, ideas will feel disconnected from the challenge at hand.

Here’s where the "How Might We" (HMW) method comes in — a deceptively simple but powerful approach to framing challenge questions that lead to better ideas. It's a technique used by design thinking pioneers like IDEO and adopted by innovative companies from Google to Airbnb.

So, what makes these three words so special?

How: Suggests we don't have the answer yet but assumes one exists.
Might: Creates space for multiple possibilities, not just one "right" solution.
We: Invites collaborative thinking and shared ownership.

Together, “how,” “might,” and “we” create an optimistic, possibility-oriented framing that guides teams toward constructive problem-solving.

From Vague to Specific: Transforming Your Challenge Questions

The difference between a mediocre and brilliant "How Might We" question often comes down to specificity. Take, for example, these no-so-great questions:

"How might we be more creative?"
"How might we reach voters?"
"How might we improve our meetings?"

These questions fall flat because they're too broad, lack context, and don't provide enough constraints to guide meaningful ideation.

But these questions — more specific, more intentional — can immediately lead to idea generation:

"How might we be more creative?" → "How might we create consistent space for creative idea generation during our product development cycle?"
"How might we reach voters?" →"How might we reach infrequent voters ages 18-21 in Philadelphia during the final week before registration closes?"
"How might we improve our meetings?" → "How might we redesign our weekly team meetings to ensure we hear every voice and leave with clear action items?"

The stronger questions include specific contexts, audiences, or outcomes that provide just enough structure to fuel focused creativity.

Using the “SPIKE” Method to Refine Your Challenge Question

"The Spike Method" can be used to improve your challenge questions. Before finalizing your HMW question, apply these five criteria:

Simple: Is your question easy to understand? Is it really more than one question rolled into one?
Penetrable: Does your question go deep enough? Does it address what you really want to explore?
Inspiring: Does your question energize you? Do you genuinely care about finding an answer?
Knowable: Do participants have the information required to answer this question?
Eloquent: Is each word serving a purpose? Can you make the question more transparent or more precise?

Let's apply these criteria to transform a real challenge question:

Original: "How might we improve customer satisfaction?"

Applying the criteria:

Simple? Yes, but perhaps too simple.
Penetrable? Not really — it doesn't dig into specific aspects of satisfaction challenges.
Inspiring? Not particularly — it's too generic to excite new ideas.
Knowable? Partially — we may have some customer data, but the question is too broad.
Eloquent? It could be more precise.

Refined: "How might we redesign our onboarding process to reduce the three most common customer support requests during the first week of use?"

So much better! This question provides clear boundaries while leaving room for creative solutions.

How to Run a 'How Might We' Session

Now that you understand the power of a well-crafted challenge question, here's how to put it into practice with your team:

Start with the problem statement: What issue are you trying to solve? Write it down in simple terms.
For example: We need a marketing calendar that leverages internal product milestones as well as capitalizes on relevant cultural moments.
Draft your initial HMW question: Transform your problem statement into a "How Might We" format
Test and refine: Apply the five criteria from the SPIKE Method to refine your question.
Share the question before the brainstorm: Give participants time to reflect on the challenge question before the meeting.
Keep the question visible: During your brainstorming session, display the HMW question prominently to keep everyone focused. Repeat the question so people stick to the prompt.
Revisit if needed: If the brainstorm stalls, be willing to refine your question further.

A Real-World Example

One team I worked with struggled to generate meaningful ideas about how to drive recurring donors in their online fundraising program. Their original question was, "How might we increase the number of recurring donors?"

We worked together to refine it to "How might we demonstrate the value of a recurring gift to our existing community of small-dollar donors?" The results were immediately more specific and targeted.

From Question to Ideas

A great "How Might We" question is just the beginning. The magic happens when you use that well-crafted question to guide a structured brainstorming session. Here's where facilitation skills come into play:

Use the question to evaluate ideas as they emerge.
For example, if you want to grow your recurring donor base from your existing one-time donors, ideas should solve the challenge.
Return to the question when conversations veer off track.
Reference the question when prioritizing which ideas to pursue.

Remember: the quality of your ideas is directly related to the quality of your questions. By investing time upfront to craft a powerful challenge question, you're setting your team up for brainstorming success.

Don't jump straight to generating ideas next time you plan a brainstorming session. Take a step back and ask yourself, "How might we craft a question that will unlock our team's best thinking?"

Need help facilitating your next brainstorming session? Sticky Note Labs designs and leads collaborative sessions that deliver real results. Book a brainstorm facilitation session and see the difference a well-designed process can make.

Danielle Kantor