Asking Better Questions: How to Improve the Quality of Your Problem-Solving and Conversations

What do you value more? A great question or a great answer?

If you thought the question I just asked was hard, you probably feel it's the question.

We find that the most innovative companies and leaders start with great questions first. They challenge commonly-held convictions with questions that shake what we as a society thought were universal truths. 

Questions that led to the innovations you see today came from sequential asking, "why, what if, and how." 

• Why = Challenges convictions or the ways things have been
• What if = Opens up imagination and possibilities
• How = Identifies ways to tackle this

Now, the framework of "why, what if, and how" isn't exactly our world's biggest secret on words your questions should start with. Warren Berger proposed this question framework in his book A More Beautiful Question as a three-part system when developing innovative solutions. More on this topic in Berger's own words below:

Each stage of the problem-solving process has distinct challenges and issues–requiring a different mindset, along with different types of questions. Expertise is helpful at certain points, not so helpful at others; wide-open, unfettered divergent thinking is critical at one stage, discipline and focus is called for at another. By thinking of questioning and problem-solving in a more structured way, we can remind ourselves to shift approaches, change tools, and adjust our questions according to which stage we're entering."

Keeping with this framework, now think about the important questions the billion-dollar companies had to ask to get started:

Airbnb - 

• Why do we have to pay for hotels when we can just couch surf?
• What if we could create a platform where people know where to couch surf?
• How could we deliver this at scale and make it worthwhile for hosts/guests? 

Uber - 

• Why is the taxi/delivery system so broken?
• What if we could create a better experience for drivers and passengers to get where they need to go?
• How could we deliver this at scale and make it worthwhile for drivers/passengers? 

Headspace - 

• Why can't we give mindfulness to the masses?
• What if we could share the best mindfulness practices to the masses?
• How could we deliver this at scale and an affordable rate?

Now let me ask you this - If those companies didn't exist yet, how much would you pay to get those questions? With the proper ingenuity in answering those questions, it could have led you to a billion-dollar idea.

That's why curiosity must precede the solution.

However, this framework is not a one size fits all approach in asking great questions. This framework can work when attacking problems with a team but isn't a template for great conversations - imagine leading every conversation with "why" and try not to make your guest feel like they have to justify something.

In stimulating conversations, knowing when to use these questions and how to use questions when your audience feels safe and vulnerable is essential.

The mindset to have is to think like your favorite radio/podcast/TV host.

Typical conversation characteristics by great hosts reflect the rapid delivery of belonging cues (as referenced heavily by Dan Coyle's Culture Code):

• Safety: Active listening by the host is backed by reassuring body language such as head nods, touching, eye contact, with knees pointed toward the guest. They are energetic in response (think when a guest says something crazy and a host puts their head behind their head in disbelief). Verbal communication cues also appear often like saying their name when asking a question and timing phrases like "safe space here," or "mmhmm's" after moments reflecting pain. Tactical examples from hosts include nudges for guests to elaborate on a thought with requests like, "tell me more" (Conan O'Brien) or "talk to me" (Charlamagne the God).
• Share Vulnerability: Host reciprocates any vulnerability with acceptance and sometimes elaborates on a similar experience to create bonding and rapport. The best hosts are always able to share their viewpoints without looking like they're one-upping their guests and making the conversation about them.
• Establish purpose: The host either respectfully agrees in the person's POV or disagrees, but does so in a non-threatening way where the guest doesn't shut down. Disagreement is critical as it builds trust where the other person knows where a person stands (this is why good hosts can't be yes-folk). 
• When the above belonging cues become established, questions starting with "why, what if, and how" can start flowing without either side feeling judged.
• The pursuit of a great answer where they'll ask the same question multiple times in various ways - this allows their fellow conversationalist to elaborate further and further without thinking their initial response was wrong. After all, it is rare the first answer you get is the best-articulated answer you can get.
• Asking questions that aren't frequently asked gets people to put you in a different category. Good hosts ask questions that the guest isn't typically asked and challenges them to think. For example, instead of asking, "what would you do differently" ask, "what would you have done the same, even if there was an inevitable negative outcome?"

Great questioning comes with great practice.

So how can you practice getting better at asking questions in conversations?

• Host a podcast/webinar/show 
• Work in a role solving problems as a team (usually customer-centric)
• Facilitate networking events where you have to entertain guests
• Teach (whether in person or an online class)
• Observe service industry workers (I have had some fascinating conversations with Uber/Lyft drivers or waiters as they know when to pry/when not to)

You know you are a great conversationalist when you can get guests to apologize for giving you too much information or when time is up, and everyone wants to keep talking. This feeling signals that "we have a future together" and a critical belonging cue for developing relationships. 

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If you've made it this far in reading this article, I now ask you again - What kind of value do you place on a good question?

Whether it's a conversation or problem-solving opportunity, the value of having a great question can lead you to answers that change your perspective.

What you do with that new perspective allows you to meet your potential!

PS: For more information on how companies can ask great questions that lead to bigger innovations, we recommend you to watch our recent webinar with Fred Schonenberg of VentureFuel here. The presentation deck can be found here.