The Questions That Change Leaders with Beth Masterman | #21
Ask Don't Tell
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...
info_outline
More Yoda, Less Superhero: The Art of Accountable Leadership | #20
Ask Don't Tell
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...
info_outline
The Irreversible Step: How to Stop Playing It Safe | #19
Ask Don't Tell
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,...
info_outline
How to Sell Yourself Without Selling Out with Pat Miller | #18
Ask Don't Tell
What if the secret to sales isn’t your pitch—but your people skills? In this episode, Oscar sits down with entrepreneur and author Pat Miller, who built a multimillion-dollar construction company from her husband’s $100 layoff check. After losing everything, she rebuilt from scratch—and now teaches others how to grow, scale, and succeed without burning out. Pat reveals how she turned being “the only woman in a room full of 40 men” into a superpower, why relatability beats the hard sell every time, and how to always be on when it comes to networking and sales. Key Takeaways: ...
info_outline
The AI That’s Redefining Leadership with Jonathan Raymond | #17
Ask Don't Tell
What if you could have a leadership coach sitting beside you—24/7? Author and CEO Jonathan Raymond joins Oscar Subirats to reveal how his new AI tool, REN, helps managers have the tough conversations they usually avoid. Drawing from his best-selling book Good Authority, Jonathan shares why true leadership isn’t about fixing problems—it’s about asking better questions. Learn how to: Master the five-step “Accountability Dial” for real growth Balance authority with empathy (think: more Yoda, less superhero) Use AI to coach yourself and your team in real time A must-listen for...
info_outline
Unlocking the Hidden Decision Maker with Jake Stahl | #16
Ask Don't Tell
What if the secret to closing more deals isn’t about what you say—but who you’re really speaking to? In this episode, Oscar sits down with sales strategist Jake Stahl, who reveals his powerful STRATA framework for connecting with the hidden “second profile” inside every buyer—the one that actually makes decisions. From decoding nonverbal signals to mastering the art of empathetic check-ins, Jake shares how to move past stalls, handle objections with ease, and craft conversations that naturally lead to “yes.” Key takeaways: Why most salespeople talk to the wrong version of...
info_outline
Selling Yourself Before the Sale with Pat Miller | #15
Ask Don't Tell
What if the key to success in business isn’t your product—it’s you? In this episode of Ask, Don’t Tell, author and business coach Pat Miller shares her raw and inspiring journey from starting a construction company with just $100 to rebuilding after loss and scaling again. With over 30 years of experience, Pat has learned that trust, relatability, and relentless curiosity are the real drivers of growth. You’ll hear how she: Turned “being an underdog” into her biggest advantage Built lasting business through networking and referrals Uses rapport and open-ended questions to...
info_outline
Fertilize Your Force Field with Sheri Laine and Gary Seidler | #14
Ask Don't Tell
What if your energy was your greatest sales tool? In this episode of Ask Don’t Tell, Oscar Subirats sits down with Sheri Laine—an acupuncturist, herbalist, nutritionist, and author with nearly 40 years of experience—and Gary Seidler, longtime publisher and creator of The Immigrant’s Road podcast. Together, they unpack how balance, compassion, and human connection shape success in both business and life. You’ll hear why your personal “force field” of energy follows you into every room, how simple daily practices can restore balance, and why empathy is the key to connection. From...
info_outline
Stop Negotiating With Your Future Self with Katie Mares | #13
Ask Don't Tell
What if the biggest roadblock to success isn’t strategy—but mindset? In this episode of Ask Don’t Tell, Oscar sits down with Katie Mares, an expert in customer experience and culture transformation, to uncover how shifting personal decisions can reshape business outcomes. Katie shares how she helps organizations stop “negotiating with their future selves,” create unforgettable customer experiences, and build loyalty that lasts. You’ll hear: Why personal growth is the secret weapon for professional success How to engineer customer experiences that make people say “yes”...
info_outline
Climb Your Emotional Ladder | #12
Ask Don't Tell
Your brain is wired to keep you safe—not happy. In this inspiring conversation, Michele Phillips reveals how to reframe your thoughts, climb out of negativity, and design a future you actually want. From overcoming career ruts to navigating personal setbacks, Michele shares her “emotional ladder” method for moving up one small, sustainable step at a time. You’ll learn: Why optimism isn’t just a personality trait—it’s a skill you can build How tiny daily habits rewire your brain for success Why starting “laughably small” beats grand, unsustainable changes If you’ve ever...
info_outlineWith over 20 years of retail banking and mortgage origination experience with some of Canada’s top banks, Deren is a former Bank Executive who started his career on the ground floor as a teller. Deren has appeared on City TV and was quoted by 680 News, Mortgage Professionals Canada, REP Magazine, MortgageBrokerNews.ca and Now Magazine. He sits down with Oscar to talk about how he works with clients in a way that creates stronger relationships. He details how he goes about appraoching people while avoiding feeling too “sale-sy” or inauthentic. He gives his tips on how to come at client in a way that will feel beneficial to all parties involved.
Learn more about Deren here: https://linktr.ee/m.deren.