EP 212 - Unlocking the Power of Questions: Insights from Boaz Ashkenazy on Paper Napkin Wisdom
Updated: Jan 28

Episode 212 of Paper Napkin Wisdom brings a profound conversation with Boaz Ashkenazy, the founder of Simply Augmented, a company revolutionizing how businesses leverage AI. With a deep passion for innovation and leadership, Boaz challenges us to rethink the way we approach success, growth, and problem-solving. His mantra, "The future belongs to those who ask the right questions, not to those who have the answers," sets the tone for this enlightening episode.Â
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Boaz’s journey is a testament to the power of curiosity and adaptability. As a thought leader in the AI space and host of the Shift AI Podcast, he emphasizes that the world’s complexity demands leaders who are not just decisive but inquisitive. In this episode, Boaz shares wisdom on how asking the right questions can unlock solutions, foster innovation, and create transformative outcomes—not just in business but in life.Â
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The Importance of Questions Over AnswersÂ
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"We live in a world where change happens at an unprecedented pace," Boaz explains. "Those who cling to answers from the past often miss the opportunities of the present and future." This perspective is particularly crucial in a business environment where leaders often feel pressure to deliver immediate solutions. Instead, Boaz argues, it’s the ability to frame and ask insightful questions that opens the door to real breakthroughs.Â
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This mindset requires humility and a willingness to embrace uncertainty. "When we admit we don’t have all the answers, we create space for new ideas and collaboration," Boaz says. He credits this approach as foundational to his success in leading Simply Augmented and inspiring innovation within his team.Â
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Building a Culture of CuriosityÂ
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One of the key takeaways from the episode is the idea of fostering a culture of curiosity within organizations. Boaz highlights that leaders can empower their teams by encouraging open dialogue and framing challenges as opportunities for collective exploration.Â
"When your team feels safe to ask questions and challenge assumptions, you unlock their full potential," he notes. This not only drives innovation but also strengthens relationships and trust within the team.Â
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The Role of AI in Amplifying Human PotentialÂ
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As the founder of Simply Augmented, Boaz is at the forefront of integrating AI into business processes. Yet, he stresses that technology should amplify, not replace, human potential. "AI is a tool that can help us ask better questions and analyze data more effectively," he says. "But it’s the human element—our creativity and empathy—that drives meaningful change."Â
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Boaz shares examples of how Simply Augmented has helped businesses use AI to enhance customer experiences, streamline operations, and uncover hidden opportunities. He believes that by asking the right questions, companies can harness AI in ways that are both ethical and impactful.Â
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Key Takeaways from Episode 212Â
Questions Drive InnovationÂ
Asking the right questions leads to new perspectives and innovative solutions.Â
Take Action: Reflect on a current challenge. What questions could you ask to see it from a different angle?Â
Foster a Culture of CuriosityÂ
Encourage your team to ask questions and challenge the status quo.Â
Take Action: Host a "question storming" session in your next team meeting to uncover fresh ideas.Â
Embrace UncertaintyÂ
Admitting you don’t have all the answers creates space for growth and collaboration.Â
Take Action: Identify an area where you feel stuck and seek input from others.Â
Leverage AI ThoughtfullyÂ
Use AI as a tool to amplify human creativity and decision-making.Â
Take Action: Explore one AI tool that could streamline a process or solve a problem in your business.Â
Lead with EmpathyÂ
Combine data-driven insights with empathy to make decisions that resonate.Â
Take Action: Evaluate a recent decision. Did it balance logic and compassion?Â
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A Call to ActionÂ
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Boaz Ashkenazy’s insights remind us that leadership is not about having all the answers but about cultivating the courage to ask better questions. As you reflect on this episode, think about how you can integrate this wisdom into your personal and professional life. What is one question you can ask today that could spark transformation?Â
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We challenge you to write your biggest takeaway on a paper napkin and share it on social media using #PaperNapkinWisdom. Let’s inspire each other to embrace curiosity and create a brighter future together.Â
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Connect with Boaz:Â
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