True Curiosity in Leadership with Jon Bassford
In this episode of the Voice of Influence Podcast, host Andrea engages with Jon Bassford, a seasoned operations professional and entrepreneur known for his powerful curiosity. Jon discusses how his inquisitive nature has driven his success from law school to leading operations for venture-backed startups and global nonprofits. He details his journey in refining organizational processes and emphasizes the importance of curiosity in leadership, as explored in his book, The Curious Leader: Unlocking Innovation, Empowering Teams, and Driving Change. Jon shares insights on how curiosity can help build a psychologically safe work environment, facilitate decision-making, and foster a culture of continuous improvement and innovation within organizations.
Mentioned in this Episode:
www.think-lateral.com
www.jonbassford.com
Text “Chapter” to 33777 for a PDF of the first chapter of the book The Curious Leader
Mentorship Guide – This VOI guide and journal for mentors and mentees includes 12 sessions covering key topics young professionals need to set themselves up for success at work.
Listener Feedback Form – Share how you see people shaping the future – and/or ask a question for Andrea and guests to address on the show!
00:00 Introduction and Guest Welcome
00:44 Jon‘s Early Curiosity and Background
01:55 Realizing the Power of Influence
05:44 The Curious Leader: Characteristics and Shifts
07:17 Psychological Safety and Organizational Culture
13:55 Balancing Curiosity and Decision Making
18:23 Curiosity in a Crazy World
21:26 Curiosity to Diffuse Problems
22:23 The Essence of True Curiosity in Leadership
22:57 Creating a Psychologically Safe Culture
23:53 The Importance of Asking the Right Questions
26:36 A Personal Anecdote on Effective Questioning
29:47 Rebuilding Operational Teams
35:41 Navigating Change and Redirection
39:52 Insights on Writing ‘The Curious Leader’
41:04 Connecting and Expanding: Personal and Professional Growth
41:54 Mentorship and Encouraging Exploration
44:10 Final Thoughts and Challenges for Future Leaders
Summary:
Have you ever felt like you were meant to make a difference, but weren’t sure how? Jon Bassford has lived that question. From questioning authority as a kid in Decatur, Illinois, to becoming an operational expert and published author, Jon has harnessed his innate curiosity to drive transformation in startups, nonprofits, and global teams.
Now, as the author of The Curious Leader: Unlocking Innovation, Empowering Teams, and Driving Change, Jon is on a mission to show leaders that curiosity isn’t a soft skill—it’s a strategic advantage.
In this episode of the Voice of Influence Podcast, Jon shares why curiosity is so vital right now—and how you can activate it in your leadership. 🎧 Don’t miss the full conversation.
Curiosity Builds Cultures That Speak Up
“Being willing and able to ask questions—and have them asked of you—is fundamental to curious leadership,” Jon says.
Curiosity isn’t just about asking questions. It’s about creating an environment where questioning is welcomed from every level of the organization. Jon draws a direct line between curiosity and psychological safety, referencing Google’s Project Aristotle: successful teams thrive when everyone feels safe to speak up.
Too many leaders expect transparency from others without offering it themselves. But curious leaders flip the script—they challenge the status quo and build trust by modeling vulnerability and openness.
“Unless you are the lead singer of a one-person band, you’ve got to bring the team along with you.”
Redirection Is More Powerful Than Change
Jon shared a powerful moment from his time as a COO when an entire organization needed to shift course after years of decline. Rather than blame individuals, he reframed his approach:
“The very word change was becoming a sticking point. People thought I was saying they’d done something wrong. So I started using the word redirection instead.”
This simple pivot—from change to redirection—deescalated fear and opened the door for collaborative transformation. True operational excellence, as Jon defines it, is not about perfection. It’s about achieving results as efficiently and effectively as possible, and that requires helping people let go of shame and step into purpose.
Curiosity Leads to Better Decisions—If You Ask the Right Questions
“Sometimes we solve the wrong problem because we’re not asking the right questions,” Jon says.
In both life and business, we can get caught in analysis paralysis—endlessly collecting information without making a decision. Curious leaders know when to ask “Why?” but also when to say “Enough.” The key? Ask with intention, not judgment.
“Be curious, not judgmental.” (Yes, he credits Ted Lasso.)
From using vendors to vet each other, to reframing conversations with his team and even with his wife, Jon demonstrates how asking better questions leads to better solutions.
In a Noisy World, Curiosity Grounds Us
We’re inundated with change, uncertainty, and distraction. But curiosity helps us re-center. Jon’s challenge to leaders is simple but profound:
“Learn to be curious and question. That’s how we improve and grow—not just as leaders, but as people.”
Whether you’re leading a team, managing a household, or shaping a global initiative, curiosity can be your superpower.