How to lead with questions, not perfect answers

Guest Post by Gustavo Razzetti

“Bureaucracies are built by and for people who busy themselves proving they are necessary, especially when they suspect they aren’t.” — Ricardo Semler

Leaders are expected to be perfect (though they shouldn’t be).

That’s why, in many organizations, being right equals to having authority — certainty is rewarded, and questions are not allowed. The lack of a challenging mentality is an expensive mistake to make — companies end solving the wrong problem.

Leadership models need to shift from owning knowledge to promoting a culture of curiosity.

Managers are not meant to solve for everyone’s problems — people have the ability and responsibility to find their own solutions. Encourage people to ask questions. Hold back your impulses; resist the temptation for (any) quick answer.

Leading with questions is an invitation for everyone to think.

The beauty lies in the question

How people deal with questions says a lot about your organizational culture. As I observe helping teams become more innovative, the companies that resist change the most tend to ask very few questions.

A more autonomous workplace is challenging power-driven’ executives — they fear their expertise and authority can lose relevance. That’s why they don’t encourage dissent — they protect their positions by owning the answers. However, providing wisdom is a more effective way of staying relevant — that’s the power of questions.

Wise leaders don’t pretend to know it all — they are comfortable challenging their own assumptions. Wisdom, like leadership, is not defined by a title.

We all want answers. However, wise people encourage us to find solutions on our own terms. They coach us to ask better questions — the beauty of problem-solving lies in the journey.

Wise leaders challenge people to look beyond lazy solutions. Easy access to information promotes short-term curiosity. Most individuals seek easy answers, not true knowledge — 95% of people don’t check past Google’s page one results.

Beautiful questions move us from our comfort zone to the discovery zone.

A beautiful question is an ambitious yet actionable question that shifts the way we perceive or think about something, according to Warren Berger. The author of A Beautiful Question, coined that term to refer to a catalyst that can uncover change and possibilities.

Berger focuses on questions that can be acted upon. That’s where the beauty lies — it’s not about creating a philosophical debate, but to provoke deep thinking to uncover practical solutions.

Leaders must help their teams rediscover the beauty within questions — quick short-term fixes are anything but beautiful.

How you can lead with questions?

“Questions are the frames into which the answers fall.” — Tina Seelig

1. Challenge existing assumptions

Perfectionism is the enemy of change; it’s impossible to improve something when we believe there’s nothing wrong. Blind spots get us into trouble — what individuals or teams don’t know they don’t know causes the majority of corporate failures.

“If I leave the company, what would you like the new CEO to change.”

Many organizations don’t encourage people to ask questions — challenging your boss, or the status quo is seen as disrespectful. However, not acting upon the issues can cause more harm than putting someone’s prestige at risk.

Start by challenging your own assumptions. Embracing vulnerability rather than certainty is anything but weakness — it’s a clear proof of your commitment to continuous improvement.

2. Reframe the real problem

We all jump way too fast into finding solutions. However, sometimes our creative juices can harm us — the rush to show how smart we are moves us into answering the wrong question.

Why should you be stuck without a bed if I’ve got an extra air mattress?

Airbnb’s $10 billion valuation all started with a Beautiful Question, as Berger explains in his book. Beautiful questions are not just about you; they help realize other people’s problems.

Brainstorming questions, not ideas, forces us to focus on better understanding the problem, rather than jumping into the solutions. Why does the problem exist? What does it say about our company? Is there a more significant problem behind it that we are missing?

Brainstorming questions helps people dig deeper into a problem — solving the right challenge starts by challenging the problem itself.

3. Create a culture of curiosity

Curiosity is the mother of innovation. To unleash your team’s creativity doesn’t require complicated questions. Sometimes, simpler questions can find solutions behind the status quo — the devil is in the details.

“Why do we want kids to sit still in class?”

Curiosity is about challenging our daily reality — what others accept as ‘normal,’ you turn it into a question. A report from the Institute of Medicine concluded that active children show greater attention, have faster cognitive processing speed and perform better.

Turn asking questions into ongoing practice. A culture of curiosity also leverages the power of quiet people — introverts feel more comfortable asking questions that sharing their ideas out loud.

4. Coach people to ask better questions

Our brain likes to ask lazy questions — we substitute questions with easier ones to save energy and time. As Nobel laureate and psychologist Daniel Kahneman explains: “When faced with a difficult question, we often answer an easier one instead, usually without noticing the substitution.”

“How can we play better?” versus “What’s driving our success?

Don’t focus on the positive. People are less likely to lie when questioners make pessimistic assumptions versus optimistic ones, as different studies show.

Avoid closed questions; they force us to select between existing options. Suboptimal questions make us settle for lazy answers — sometimes the best solution is to unanswer the question, as I wrote here.

Encourage your team to challenge the questions — don’t settle for lazy problems.

5. Use questions to encourage transparency

Every individual in your organization is a sensor. The increasing complexity and speed of businesses require paying attention to every signal — when a problem makes it to the top, it might be too late to fix it.

“What is everyone thinking but no one is saying?

A culture that encourages people to ask questions increases communication, collaboration, and transparency. It facilitates identifying and addressing tensions before they escalate and create more harm.

Transparency removes the drama behind questions — rather than being defensive; people enjoy the challenge. It creates an open-dialogue culture — people provide feedback via “what if?” rather than “you should … ”

For some people, questioning is a natural skill; for most, it needs to be nurtured.

Creating a culture of curiosity takes time. Most people are wired to impress others with their smarts rather than to challenge reality — they need to become comfortable with navigating uncertainty.

The power of questions lies in unlocking value in organizations. It turns blindspots into bright spots, it fuels innovation and continuous improvement, it creates a culture of transparency and collaboration, it focuses our effort on solving the right problem and builds trust.

Leading with questions is a beautiful and effective habit.


Gustavo Razzetti


Gustavo Razzetti  is the CEO of Liberationist, a change leadership consultancy that helps organizations become more innovative. His human-centered approach liberates the within every team. Gustavo has over 20 years of experience transforming people’s behavior at the intersection of Neuroscience, Design Thinking, Mindfulness, and Creativity.  He is also a regular speaker and has facilitated hundreds of change workshops in the US, Europe, and Latin America. You can request Gustavo’s free eBook” “Stretch Your Team”  by clicking “HERE”


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