Jon Bassford on The Power of Asking Questions & The Curiosity Superpower! | Tony DUrso

Jon Bassford is an operations professional and entrepreneur who thrives on curiosity—his ultimate superpower. After law school, he leveraged this strength to launch, manage, and optimize operations for everything from venture-backed startups to global nonprofits. Jon believes that curiosity fuels innovation, problem-solving, and leadership at every level.
His latest book, The Curious Leader: Navigating the Power of Asking Questions and Fostering a Culture of Inquiry, unpacks how mastering the art of questioning can drive innovation, improve decision-making, and create a more engaged workforce.
Later in this episode, we explore Step 6 of The Vision Map™: Tactical Plan, revealing how to transform strategic goals into actionable steps that lead to real results. Plus, get the full 8-Step Vision Map™ Guide—your roadmap to success—by joining my newsletter at tonydurso.com.
I also break down three critical social media mistakes you absolutely must avoid if you’re serious about growth. Cracking the social media code is essential, and I share powerful lessons that can help you stand out, engage, and succeed. Don’t miss it!
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Jon Bassford is an operations professional and entrepreneur who thrives on curiosity—his ultimate superpower. After law school, he leveraged this strength to launch, manage, and optimize operations for everything from venture-backed startups to global nonprofits. Jon believes that curiosity fuels innovation, problem-solving, and leadership at every level.
His latest book, The Curious Leader: Navigating the Power of Asking Questions and Fostering a Culture of Inquiry, unpacks how mastering the art of questioning can drive innovation, improve decision-making, and create a more engaged workforce.
Later in this episode, we explore Step 6 of The Vision Map™: Tactical Plan, revealing how to transform strategic goals into actionable steps that lead to real results. Plus, get the full 8-Step Vision Map™ Guide—your roadmap to success—by joining my newsletter at tonydurso.com.
I also break down three critical social media mistakes you absolutely must avoid if you’re serious about growth. Cracking the social media code is essential, and I share powerful lessons that can help you stand out, engage, and succeed. Don’t miss it!
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Transcript
Show Notes
[11.22] Curiosity in Leadership: Unlocking the Key to Growth and Operational Excellence
- Curiosity plays a vital role in entrepreneurship and business leadership by fostering a growth mindset.
- It drives operational excellence by helping leaders analyze their actions and refine processes for better results.
- A curious leader embraces change and is always asking questions about what, why, and how things are done.
- Leaders must cultivate a curious culture within their teams to engage employees and encourage them to think creatively.
- Curiosity enables leaders to break free from old habits and look at their organizations with a fresh perspective.
- It’s about questioning the current way of doing things to ensure that processes are effective and drive intended results.
- Curiosity also helps solve problems by allowing leaders to dig deeper and address the root causes, rather than just symptoms.
- Effective problem-solving requires letting go of the assumption that a leader’s initial ideas or strategies will always be right.
- Embracing curiosity ensures that businesses remain adaptable, helping them avoid the pitfalls of becoming stagnant or outdated.
[21.41] Creating a Curious Culture for Problem Solving and Innovation
- Jeff Bezos once emphasized that asking the right questions is crucial to solving problems. For example, instead of providing knee pads to solve the issue of employees working on their knees, a packing table was introduced to address the real problem.
- Being curious means identifying the root causes of issues, not just addressing their symptoms.
- A curious leader asks the right questions to understand why problems arise, allowing teams to dive deeper into solutions.
- For example, rather than simply asking why sales are down, a curious leader would probe with questions like, “What factors are affecting our sales?” or “What’s causing this drop?”
- Creating a curiosity-driven environment requires leaders to foster an open culture where employees feel safe to give feedback, ask questions, and offer solutions.
- Psychological safety is key to this environment. Google’s Aristotle Project found that teams who feel psychologically safe are more innovative and open to feedback.
- In a curiosity-driven culture, everyone’s perspective is valued, breaking down silos and enabling collaboration across departments.
- Leaders must be willing to accept feedback and engage in dialogue with their teams, allowing for the free exchange of ideas.
- A curiosity culture encourages constant questioning and analysis, which helps organizations evolve and stay adaptable to changing conditions.
[31.00] Embracing the CEO’s Evolving Vision and the Role of Team Input
- CEOs and founders often face a difficult dilemma—holding onto their original vision while adapting to new ideas brought by their teams.
- It’s natural for founders to want to protect their company’s early concept, which they worked hard to build. However, a stagnant vision can hinder growth.
- A curious leader is willing to accept that their vision may need to evolve over time, much like how the film Blockbuster couldn’t foresee the rise of digital streaming.
- The CEO’s responsibility is not to have detailed knowledge of every department, but to rely on experts who bring in their unique perspectives.
- A CEO who micromanages every detail limits the organization’s potential for innovation and growth.
- Leaders should encourage a culture where employees feel comfortable questioning processes and suggesting new ideas, as each department will have its own insight on the company’s challenges.
- When different teams (sales, marketing, legal, etc.) are able to freely share their perspectives, they can uncover new solutions to problems that were previously overlooked.
- By creating an inclusive environment, where questioning is encouraged, a CEO can help the company avoid complacency and keep pushing toward progress.
- Fostering a curious and collaborative culture allows employees at all levels to contribute ideas and actively shape the organization’s future.
[38.02] The Role of Curiosity in Innovation and Leadership Development
- Curiosity cultivates growth by encouraging constant questioning of the status quo and allowing room for mistakes, which are essential for innovation.
- CEOs who foster curiosity in their teams create a culture of experimentation, where new ideas can be explored without fear of failure.
- An organization that promotes curiosity is more likely to uncover solutions to problems that may not be apparent through traditional methods.
- Curiosity also breaks down the barriers of a hierarchical structure, ensuring that every team member’s perspective is valued.
- Leaders should embrace the idea that they don’t have all the answers. Instead, they must trust their teams and encourage an open dialogue about improving the organization.
- Mistakes are inevitable, but they provide valuable lessons. By creating a culture where failure is accepted as part of the learning process, leaders can inspire their teams to take risks and innovate.
- Being open to new ideas allows organizations to adapt quickly, particularly in fast-changing industries, and prevents them from falling behind competitors.
- Curiosity isn’t just a tool for problem-solving; it’s a mindset that leaders should cultivate within themselves and their teams to drive continuous improvement.
- This mindset helps businesses not only survive but thrive by ensuring they stay flexible and open to change as they scale and evolve.[45.41] The Power of Curiosity in Unlocking Organizational Potential
- Curiosity can spark transformative change in any organization, much like when an employee asks questions to dig deeper into processes that are often assumed to be fine.
- In the case of one company, a simple question about an important document led to a dramatic 20% increase in revenue and a 500% boost in programming and event attendance.
- The root cause of a business challenge is often hidden beneath surface-level assumptions, and curiosity is the key to uncovering those deeper issues.
- For example, when the CEO of an organization was confronted with declining sales, the right question wasn’t simply about sales numbers, but about why sales were down and what could be improved.
- In a culture of curiosity, asking “why” is the first step toward solving any problem, especially when leadership encourages open dialogue.
- It’s important for CEOs to realize that no one person—no matter how experienced—is expected to have all the answers to every problem.
- Allowing employees at all levels to contribute their perspectives fosters a diverse, collaborative approach to problem-solving.
- A company built on curiosity is one where individuals feel safe enough to ask tough questions, challenge norms, and offer solutions without fear of judgment.
- By embracing curiosity and letting go of the fear of failure, organizations can unlock their full potential for growth and innovation.











