As soon as we learn to speak, we begin asking “why?” Why is the sky blue? Why are caterpillars fuzzy? Why does a triangle have three sides? In one poll people estimated that 70-80% of their kids’ conversations were questions. But those same professionals reported that only 15-25% of their own interactions were questions. Why do we stop asking? Often, it’s fear. Fear of looking stupid. Fear of acknowledging we don’t know the answer.
But when we stay silent, we undercut our growth and that of our team. Good questions are critical elements of good conversation. They are power tools for learning, innovation, and collaboration. They unleash new ideas by surfacing the insights of others. And they power inclusion, by signaling deep respect for the value of someone else’s contribution.
When we tap into the wonder and honest curiosity of childhood questions. When we eschew “gotcha” inquiries designed to test or trap someone else. When we frame questions to elevate discussion and transform thinking. Only then, can we change the way we work together – building trust, deepening relationships, fueling innovation, avoiding risks, and unlocking growth.
“A participant recently commented that one of the most powerful moments of his Reflection Point experience was instigated by the facilitator asking a question that changed everything. He “pulled on a thread in the story that was less obvious, and it changed my point of view entirely.”
—Reflection Point Participant
"The openness of discussion and thought-provoking questions caught me by surprise in an uncomfortable way. And I was grateful - because this is often where new insights take place.”
—REFLECTION POINT PARTICIPANT
We will never get the answers to the questions we fail to ask. When we stop at shallow or transactional questions, we are leaving too much on the table. But asking better questions is a skill we need to master. Like any skill, the only way is to “practice, practice, practice.”
To practice asking bigger questions, start small. Every time you ask a transactional “what” or “how” question, pause to add a “why” or a “what if” or a “what could be.” For every answer that seems to take you down a different path, simply add an extra prompt: “please say more.”
By opening the window a little further, we tap into new ideas, see others in a new light and deepen our understanding. We become more attuned investigators, seeking to learn more and improve our collaboration and innovation.
In a changing and challenging world, can we afford not to ask the best questions we can?
Questions Can be as Powerful as Answers
Hal Gregersen, author of “Questions Are the Answer” advocates for question bursts to replace brainstorming in the quest for innovative ideas.
In a set time (usually four minutes) the team asks as many questions as they can about the problem. No one is allowed to answer or explain why they’re asking the question, and every question is transcribed. Focusing on questions instead of answers takes people out of the traditional construct and into new, often revelatory, territory. At the end, the team reviews the questions and decides which ones need more research.
After analyzing thousands of question bursts, Gregersen has found that at least 80 percent of the time the challenge is slightly reframed in a better way, and at least one valuable new idea is generated.
Reflection Point’s approach works because it’s grounded in science and the latest research on organizational learning.
People who ask good questions are better liked.
A Harvard study in 2017 found that people who ask more questions, particularly follow-up questions, are better liked than people who ask fewer questions. That’s because people who ask more questions are perceived as higher in responsiveness, which translates to being perceived as someone who listens, understands, validates, and cares – all traits that fuel better collaboration at work.
Asking good, curious questions deepens connection.
A famous study by psychologist Arthur Aron in 1997 used a series of 36 increasingly probing questions to make complete strangers fall in love in his lab. The questions were so powerful at spawning deep connections that they’ve spawned countless romances and marriages – as documented in a viral Modern Love Column in the New York Times. They’ve also been used in scores of other research experiments and many other applications such as improving understanding between police officers and community members in cities where tensions run high.
Asking great questions spurs innovation.
In a six-year study of entrepreneurs, inventors and founders, Jeffrey Dyer, Hal Gregerson, and Clayton Christensen found that questioning was one of five crucial “discovery skills” that distinguished the most successful leaders. They found three attributes of good question askers:
Have you ever gotten advice from a mentor that didn’t sit well? Advice that disregarded the essence of who you are?
A team of marketing colleagues in a large global tech company recently pondered this question in a Reflection Point session. One young man reflected on times he felt he had to change to fit others’ expectations. “Shapeshifting,” he called it. “If you change your identity so easily, so quickly, how do you retain the real you?”
How did the group get so candid so quickly? We started with a story.
Meet Dolapo Owolabi, a graduating university student in Britain with designs to enter the banking world. A well-meaning mentor (hired to help companies recruit minority students) schooled her on her name (call yourself “Dolly” instead) and her hair, the large afro Dolapo dearly loved.
With Daisy’s encouragement, Dolapo purchased new hair at a cost of 300 pounds (hair that came from an Indian girl named Sunita), and had it woven and stitched into the tight braids of her natural hair. She became Dolly with straight hair and the “right” clothes, but remaining Dolapo underneath, struggling to recognize herself.
Dolapo is the protagonist in Nigerian author Chibundu Onuzo’s short but powerful story, “Sunita.” The first question posed to the group: “Was Daisy a good mentor?”
They felt Dolapo emerges triumphant in the story (spoiler: she stands up for herself and goes to her interview as Dolapo with her natural hair). Sunita’s experience is a little more sobering. Her hair now neatly woven to Dolapo’s scalp, she suffers the torments of her schoolmates as she appears at school with a shaved head. She literally fights the boys to preserve her dignity.
“She made a choice” to sell her hair, one person gingerly offered. But another asked whether she really had a choice - or simply an economic reality she could not avoid? “We live in a stratified social structure - built so that we don’t have to face the discomfort of our own choices,” one participant concluded, opening the discussion to both the personal and business implications of the illusion of choice.
A short discussion on an arresting story made us question our choices, assumptions, and perspectives. A reflection point indeed.
“The story got me thinking about the power of mentorship and how well I mentor others. I will think about the unique needs of each person I mentor to avoid giving advice that might not fit.”
—REFLECTION POINT PARTICIPANT
Reflection Point uses hundreds of different stories, so we can choose the ones that unearth the right themes and discussions for your organization. Here are two examples:
“Menagerie, A Child’s Fable” by Charles Johnson
In this 1980s fable, the owner of a pet shop fails to come to work one day. When the animals take over the store, brutal mayhem ensues as they compete for food and power. The often-shocking behavior of the animal characters becomes an arresting commentary on the state of humanity as a diverse global community. The story addresses universal themes of freedom and oppression, racism and pluralism, democracy and fascism, and war and peace.
“The Book of Martha” by Octavia Butler
In this short story, God asks the main character, Martha, to propose one change that would help humankind find “less destructive, more peaceful, sustainable ways to live.” Martha and God discuss all the possible outcomes and unintended consequences of different interventions. The story asks us to consider the personal sacrifices necessary to make a more just or equitable world, and the ways in which our personal experience colors what we see. It also opens a window onto the interdependence of systems and the ways in which an “investment” in the future cannibalizes the present.
When we bring colleagues together to share perspectives and reflect on powerful stories like these, we start conversations we wouldn’t otherwise have. We melt hierarchies and level the playing field. We kickstart connection, relationships, and, ultimately, collective intelligence.
In a hilarious courtroom scene in My Cousin Vinny, a spiteful district attorney in an Alabama murder case tries to discredit the glamourous, if unorthodox, automotive expert witness, Mona Lisa Vito. His attempt backfires when his smug attempt at a “gotcha” question reveals her encyclopedic knowledge of cars, gleaned from growing up in her father’s Brooklyn auto repair shop. He underestimates her, at his own expense.
Seasoned trial lawyers abide by an age-old rule: “never ask a question if you don’t already know the answer.” In a context where questions are part of a choreographed dance to make or defend a point, surprising answers are never a good result.
While this technique may prevail in court, it falls far short in all other workplaces. Yet leaders use it all the time. They ask questions designed to verify what they already know or believe, rather than learn something new. If you use questions just to gather data to prove your point, you leave far too much on the table.
“Good questions are power tools for collaboration and innovation. But only when they are grounded in honest curiosity and a genuine desire to hear the answer - even if it’s not what you expect. Asking good questions unleashes new ideas by surfacing the hidden insights of others. And it signals your respect for colleagues and the value of their contributions.
Teams that understand and use the power of honest questions are more collaborative, innovative, and inclusive. Here’s how to do that:
Change it up. Many leaders have predictable patterns of behavior, especially
in meetings. Your colleagues will prepare to answer the questions they know you will ask. If you stick to your usual script, the answers you get will never stray from the familiar. Think about why you ask a particular question and frame it differently. Instead of narrow questions about facts or deliverables (what is, what are), ask broad, open-ended questions that make people pause and reflect (what if,
what could be). These open questions are designed to invite broader thinking
and surface innovative responses: “If we could remove all constraints, what
might be possible?” Probing questions deepen exploration. There is no better question to refine someone’s thinking and expand a conversation than a simple “please say more?”
Slow down. Asking better questions requires you to change how you ask: being ready to challenge your own belief systems, to acknowledge that you don’t already have the answers. Being willing to ask a question whose answer will cause you to pause helps you think about a problem or a situation from another’s perspective, and models genuine collaboration. It’s the subtle shift from a fixed to a growth mindset, where the ask itself signals your willingness to learn something new. Resisting the push to get quickly to an answer allows you and your team to be curious, to explore diverse possibilities and embrace out-of-the-box ideas
without fear: “What could we try that might not work?” In a time-starved culture, this is hard. But good ideas - especially novel ones - take time to build and freedom to mature.
Don’t be afraid to ask hard questions. Author Peter Block defines three attributes for a good question: it must be personal, ambiguous and evoke anxiety. Anxiety, in this case, is not about intimidation, it’s about importance: the things that make us anxious are the things that matter. A personal question engages the heart as well as the head, encouraging the listener to bring more of themself to the challenge. And an ambiguous one requires you to rely on the listener to provide the meaning. This framework invites you to rethink what you ask your colleagues. Hard questions introduce vulnerability and produce deeper, often unexpected answers. These questions jostle the status quo, encouraging you and your colleagues to push beyond your comfort zones: “What are we doing today that no longer serves us?” These are fundamental or existential questions that encourage your team to dig deep and put the inquiry before personal interest. How do you know that you’ve asked this kind of question? When you have no idea how to answer it yourself.
It’s easy to fall into a transactional trap: using questions to gather the data you need to confirm a decision or point of view. Too many leaders assume – like that Alabama district attorney – that they already know what others have (or don’t have) to offer. They underestimate their teams, at their own expense.
The world is just too complex for anyone to have all the answers. Build a culture of genuine curiosity that embraces this. It sounds extreme but try asking questions like you know nothing and it will not only change the conversation – it will change your team, your productivity, and boost your innovation for the better.
