Break the discussion deadlock with “How Might We”?

May 10, 2020
“We cannot solve our problems with the same thinking we used when we created them.” - Albert Einstein

How to handle conflicts? How to brainstorm or lead an ideation session effectively? Have you been to a workshop, a team meeting or a discussion where it was difficult to find common ground among multiple stakeholders with differing points of view? Can you recall a moment where diving deeper into a problem or issue served to only entrench the deadlock further among the stakeholders?

When frustrations and tempers rise, communication can begin to break down and ‘negotiation impasse’ sets in. Skilled facilitators do not start discussions with disagreements, as this brings to the fore feelings of negativity. A key strategy in neutralising the blocks and restarting the discussion is to establish a common ground.

At OPPI, we use the power of AI to crowdsource opinions and ideas in order to find common ground on issues that are divisive, complex and polarizing. Our technology helps opinion groups or tribes at odds with one another to locate shared values by sieving out commonalities between them.

The secret to OPPI’s ability to find common ground lies in the art and science of crafting “How Might We” (or “HMW”) questions. From our experience, the “How Might We?” question actually makes or breaks the entire process of co-creating solutions that are amenable to all the stakeholders. Getting this first step of the process right is paramount for the quality of the discussion that ensues between participants.

“How Might We?” questions are one of the tools designers and innovators use to open up brainstorming and ideation sessions. A well-crafted HMW comes at the crucial transition between the first 55 minutes of problem framing and the last 5 minutes of ideation (in the context of Einstein’s following quote):

“If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.” Albert Einstein

The 3 parts of a HMW question are:

  • 1. “How” encourages the group to indulge in speculative and divergent thinking and not convergent thinking.
  • 2. “Might” allows for exploration of multiple possible solutions, not settling for the first that comes to mind.
  • 3. “We” immediately brings in the element of a collaborative effort. It engenders a sense of social inclusion and accountability.

2 examples of HMW questions in OPPI’s latest contentious poll discussions with Singapore citizens were:

“How might we encourage the public to embrace migrant workers’ needs in Singapore during and after the pandemic?
“How might we revise manpower policy and economic strategies in response to the current situation for migrant workers in Singapore?”

There are 3 components to a well-crafted HMW statement:

Craft your How Might We statement with the above 3 components

The 2 HMW examples are broken down into their respective components in the table below:

The 2 How Might We statements are broken down into their 3 components above

Having practised the art and science of crafting “HMW?” questions, we at OPPI have distilled 5 principles or best-practices that any facilitator, designer or innovator could adhere to in crafting good quality HMWs:

Principle 1: A good HMW statement is narrow enough to be manageable, yet broad enough for creative freedom.

It’s a tricky process but a good HMW should not only give us a narrow enough frame to let us know where to start our brainstorm, but accord us enough breadth to explore wild ideas and to stretch boundaries. A well-framed challenge has just enough constraints, with space to explore.

Principle 2: Don’t settle on your first HMW draft.

First draft statements are usually diamonds in the rough. Like naturally occurring diamonds, first drafts are quite ordinary at first glance; their true beauty as jewels is only realized through the cutting and polishing process. It is good practice to test your HMW questions on and get candid feedback from a diverse set of stakeholders to mitigate anchoring and availability biases.

Principle 3: Solve for the HMW problem and the HMW solution in parallel.

The HMW framing is in stark contrast to linear problem solving, which rationally attempts to define everything upfront, and then etch away at achieving the set solution systematically. HMW’s unique approach is as much about uncovering the problem as it is about etching away at an amenable solution.

“Designing a campaign which increases sign-ups to our event.” is an example of a linear problem. A linear problem often puts a patch on things, dealing with the symptoms of the problem. The HMW approach probes deeper into underlying or root causes of questions such as: “Why are people not signing up for the event?” or “What is it about our product that causes people to ignore it?”

Principle 4: Stretch boundaries and re-frame by taking the HMW to an extreme, exploring the opposite, questioning assumptions and creating analogies.

Lateral thinking helps us to break out of rigid thought patterns and to generate unpredictable HMWs. Lateral thinking seeks to arrive at unknown solutions, as opposed to vertical thinking, which operates directly on perceivable data and analysis.

Stimulating materials and artefacts (e.g. personas, diagrams, imagery, analogies, quotes or stories) can lift the collective cognitive load. Stimulus sparks new connections and thinking pathways, which can help lead to unexpected and unconventional ideas.

Principle 5: Nurture a diverse and psychologically safe culture and environment that stimulates creative HMW statements generation.

Bringing together a multi-disciplinary team that incorporates a wide range of thinking styles helps provide much-needed diversity. Ideation facilitation requires an expert understanding of people dynamics and how cultural factors such as vulnerability, empathy and psychological safety affect these dynamics.

Also, the ideation space should ideally be located away from the normal work environment, which can remind participants of stressful activities and time pressure. Participants should be cut off from interference from other co-workers or work activities. OPPI provides that form of ideation space by bringing people of different disciplines in an environment where ground-up ideas can be surfaced.

A good quality “How Might We?” question could be your secret to yielding high-quality discussions. If you are leading an ideation or brainstorming session, you could consider experimenting with HMWs as one of the additional tools in your facilitation toolbox. Get in touch with us at if you would like to find solutions to your organisational or societal challenges.


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