What if the biggest obstacle in your life isn't your circumstances, but the story you've been telling yourself about them?

In this episode, Oscar sits down with leadership coach, speaker, and mythologist Scott Mason to explore how hidden beliefs shape our decisions, careers, relationships, and sense of possibility. Drawing from his own journey through career collapse, serious illness, and personal transformation, Scott reveals why so many people stay stuck in patterns that no longer serve them and how to rewrite the story.

Together, they discuss: • The five toxic myths that keep people trapped in fear, self-doubt, and limitation • Why your past does not have to define your future • How small acts of courage can create lasting change and build a more powerful identity

Scott also shares the life-altering health crisis that forced him to confront his own limiting beliefs and discover a framework that has since helped entrepreneurs, leaders, and professionals break free from old narratives and step into a bigger vision for their lives.

If you've ever felt stuck, overlooked, or unsure of what's next, this conversation is a reminder that your story is not finished. The moment you challenge the myth, you create the possibility for a new future.

What if the key to growing your business is not having all the answers, but asking better questions?

In this episode, Oscar sits down with Jon Bassford, founder, consultant, and author of The Curious Leader, to explore why leaders often become the biggest obstacle to their own growth. Jon shares how helping organizations scale starts with understanding the connection between leadership, operations, and culture, and why curiosity is the missing ingredient in building stronger teams.

Together, Oscar and Jon unpack how to: • Break free from habits that keep businesses stuck • Build trust by listening instead of controlling • Use better questions to uncover solutions, improve sales conversations, and create stronger connections

Whether you are leading a company, building a business, or simply trying to communicate more effectively, this conversation will challenge you to rethink how you listen, lead, and grow. Start asking better questions, and you may discover the answers you have been looking for all along.

Most leaders are chasing performance but ignoring the one thing that makes performance sustainable.

In this episode, former FBI leader turned executive wellness coach Sarah Draper reveals why high-performing leaders often burn out, drift, or quietly struggle behind the scenes. Drawing on decades in high-pressure environments like the Army and FBI, Sarah explains why leadership starts with something many people avoid: taking care of yourself.

Oscar and Sarah explore how leaders can step out of survival mode, reconnect with their purpose, and build the physical, mental, and relational foundations that make great leadership possible.

You will learn:

• Why high achievers often wait too long to address burnout
• The simple "future walk" exercise that can reshape your goals
• How sustainable leadership starts with your health, mindset, and relationships

If you want to lead better, perform longer, and build a life that actually matches your ambitions, this conversation will challenge how you think about success.

What if the thing holding you back as a leader isn't strategy, skill, or effort—but who you believe you are?

In this episode, Oscar sits down with executive coach Jeff Munn to unpack why most founders, CEOs, and high performers stay stuck even after reading the books, attending the seminars, and "doing all the right things." Jeff shares how outdated identities, unconscious fears, and internal wiring quietly sabotage leadership, decision-making, and growth—and why tactics only work after the inner work is done. Together, they explore how powerful questions, deep listening, and silence can unlock clarity, confidence, and real change.

Key takeaways include:

• Why "what got you here won't take you there" is an identity problem, not a skill gap
• How fear—not logic—is usually the real reason people don't take action
• Why great leaders (and great sellers) ask better questions instead of giving better advice

If you're feeling stuck, overwhelmed, or frustrated despite doing everything "right," this conversation might be the wake-up call you didn't know you needed. Lean in—and be ready to rethink who's really in your way.

In this episode of Ask Don't Tell, Oscar Subirats sits down with leadership speaker and author Joel Worthington, creator of the Tell Me More philosophy, to unpack why asking better questions—not giving better directives—is the missing link in modern leadership. Joel breaks down how emotional intelligence, trust, and genuine curiosity transform disengaged employees into true followers, and why most organizations unknowingly sabotage themselves with fear-based communication.

Together, they explore how leadership is really about influence, energy, and connection—and why slowing down to ask one better question can change the trajectory of your team, your culture, and your results.

Key takeaways include:

• Why "Tell Me More" is the most powerful phrase a leader can use
• How directive leadership kills buy-in, energy, and trust
• Joel's GUIDE framework for leading with clarity, empathy, and strategy

If you want people who follow you—not just work for you—this conversation will challenge how you lead, listen, and show up every day.

Summary

In this conversation, Kevin Hubschmann discusses the concept of 'Laughter as a Service' and how comedy can be integrated into corporate environments to enhance professional skills and team dynamics. He shares insights on the benefits of improv training, the psychology of laughter, and the importance of authenticity in sales. Kevin emphasizes the need for deep discovery in sales conversations and how rebranding can help overcome objections. The discussion highlights the value of building relationships and making clients feel like rock stars through effective communication and humor.

Takeaways

• Laughter can significantly improve workplace dynamics.
• Comedy skills can enhance professional development and sales effectiveness.
• Improv training fosters better listening and collaboration skills.
• Authenticity in sales leads to stronger client relationships.
• Understanding the psychology of laughter can enhance team building activities.
• Rebranding services can help overcome common objections in sales.
• Deep discovery in conversations leads to better solutions for clients.
• Building champions within organizations can lead to long-term partnerships.
• Creating a fun and engaging environment can improve learning outcomes.
• Sales success often comes from making clients feel valued and understood.

Great businesses don't start with answers — they start with better questions. In this episode, Rachel Niederhofer, founder and CEO of Audacious Designs and Audacious Properties, shares how she blends interior design, construction expertise, and real estate investing into one powerful super-skill: solving real problems people can't articulate on their own.

Rachel reveals how she uncovers what clients really need, why emotion drives nearly every decision in design and sales, and how understanding motivation leads to higher property values, smoother projects, and stronger client trust. Her approach proves that sales isn't about pitching — it's about listening, dissecting, and guiding people toward the solution that changes everything.

In this episode, you'll learn:

• How to ask questions that move clients from "I don't like this" to the real root issue
• Why macro-to-micro questioning builds trust (and better results)
• How design strategy, construction knowledge, and motivation combine to maximize ROI
• Why finding the "why" matters more than selling the "what"

If you want to elevate your business thinking, sharpen your sales instincts, and communicate with more clarity and heart — this episode is packed with game-changing insights.

The Questions That Change Leaders with Beth Masterman

In this episode, Oscar sits down with executive coach Beth Masterman, whose winding career through law, politics, psychology, and prosecution shaped her into the rare kind of coach who can walk with clients through the most complex corners of leadership. Beth shares how she helps high-level executives navigate toxic workplaces, difficult conversations, self-doubt, and the human experience behind every professional challenge.

Hear Beth break down the coaching strategies she's refined over decades — including how to turn "why" into "what," how silence becomes a leadership tool, and why the best solutions are the ones people discover for themselves.

Key themes:

• How to use smarter questions to unlock better leadership
• Why difficult conversations fail — and Beth's repeatable formula for getting them right
• The difference between listening and really listening
• How our past careers silently shape our superpowers

By the end, you'll see leadership (and yourself) differently — and feel inspired to ask the questions that move your life forward.

What if the key to great leadership isn't fixing every problem—but asking better questions? Author and leadership expert Jonathan Raymond joins Oscar to break down his Accountability Dial, a five-step framework for transforming difficult conversations into powerful growth moments. They dive into why most leaders get accountability wrong, how to create true ownership on your team, and how Jonathan's new AI tool, REN, helps managers lead with empathy and clarity in real time.

Key takeaways:

• How to shift from "command and control" to curiosity-driven leadership
• The five stages of effective accountability conversations
• Why AI could be the next frontier in people leadership

What's holding you back from your next big leap? In this episode, former REMAX Worldwide President turned strategist Amy Lessinger joins Oscar to reveal the simple but powerful framework behind life-changing decisions. Amy shares how she went from selling homes to leading a global brand—and why focus, lead generation, and the courage to take an irreversible step are what separate top performers from everyone else.

Key takeaways:

• The one mindset shift that separates 1% producers from the rest
• Why successful people get stuck—and how to break free
• How to build a framework for bold, no-turning-back transformation