Transformative Leadership Conversations with Winnie da Silva

What does it take to drive change in a male-dominated industry while staying true to your vision? In this episode of Transformative Leadership Conversations, I sit down with Andreea Gleeson, CEO of TuneCore, to hear her remarkable story. Andreea shares how she transitioned from retail to music, the challenges she’s faced as a woman in leadership, and her mission to empower artists at every level of their careers. From tackling gender inequality in the music industry to fostering innovation at TuneCore, Andreea’s journey is one of determination, grit, and vision. Her insights aren’t just inspiring—they’re actionable for anyone looking to lead with purpose and drive change.

Listen in as they discuss:

• Breaking barriers: Andreea’s work to bring gender parity and representation to the music industry.
• Supporting artists: How TuneCore helps musicians, from beginners to global stars, build their careers.
• Lessons in leadership: The mindset and skills Andreea honed to grow into her role as CEO.
• Empowering growth: The importance of doubling down on your strengths while addressing challenges.
• Overcoming obstacles: How Andreea navigated challenges in both her career and in the industry to create lasting change.
• The power of confidence: Why confidence is a critical factor for success, especially for women working in competitive spaces.
• The art of adaptation: Andreea’s advice on how to stay adaptable and innovative in a constantly changing industry.

Resources

Andreea Gleeson on LinkedIn | TuneCore

Winnie da Silva on LinkedIn | on the Web | Substack

How do people really see you, and does that match who you want to be? In this episode of Transformative Leadership Conversations, I take a close look at what it means to shape your leadership brand authentically. Through stories from real clients and practical advice, I’ll show you how to shape and evolve your brand to resonate and stand out in ways that genuinely reflect you.

Listen in as I discuss:

• Defining Your Leadership Brand: It’s about aligning how people see you today with who you want to become.
• Lessons from Real Clients: Hear about Mark, whose value was getting overlooked, and Gary, who needed a brand refresh to succeed in a new role.
• Building Brand Consistency: Actions speak louder than words, so let’s talk about why people trust what they see—and why you need to show up consistently.
• Projecting Your Brand Effectively: I'll walk you through exercises to help make your brand come alive, so you’re recognized for the qualities you want to be known for.
• Overcoming Common Missteps: Learn about frequent branding pitfalls, like being vague or trying to please everyone, and why specificity is key.
• Expanding Your Influence: We’ll discuss ways to build a brand that doesn’t just support you internally but amplifies your impact on a larger scale.

Resources:

Winnie da Silva on LinkedIn | on the Web

How do I define success—and how does that shape the decisions I make? In this episode of Transformative Leadership Conversations, I have the pleasure of chatting with Cherie Hu, a music industry expert and the founder of Water & Music. Together, we dive into decision-making in both creative and business landscapes, exploring how our interpretations of success can shape our paths and the strategies we choose.

You’ll here them discuss:

• Redefining Success: Leaders should understand that success can be defined in various ways depending on context, extending beyond just revenue metrics to include broader impacts and outcomes.
• Balancing Risk and Stability: Having a stable foundation is crucial for organizations, as it allows leaders to take calculated creative risks without putting their well-being or financial health at risk.
• Value of Experimentation: Embracing iterative experiments provides valuable insights and data, helping leaders make informed decisions and refine their strategies more effectively.
• The Power of Storytelling: Leaders can effectively communicate difficult decisions and rally support by crafting compelling narratives that make complex truths more relatable and understandable.
• Influence of Culture and Values: The culture of a company and its commitment to social impact significantly shape decision-making processes and how relationships with stakeholders are developed and maintained

Resources:

Cherie Hu on the Web I X (Twitter) I LinkedIn

Winnie da Silva on LinkedIn I Web

What happens when the very decisions you make as a leader cause unintended ripple effects throughout your organization? In this episode of Transformative Leadership Conversations, I sit down with Prita Kumar to explore the complex balance of short-term goals, long-term planning, and the law of unintended consequences in leadership. Prita shares her experience in managing teams without overwhelming them, how she thinks about qualitative vs. quantitative data, and why creating consistency across departments is crucial for success.

You will hear them talk about:

• Prioritizing Team Focus: Leaders must be mindful of how much they ask from their teams to avoid overwhelming them with conflicting priorities.
• Balancing Short-Term vs. Long-Term Goals: In resource-rich environments, leaders can plan for the long term, but in leaner times, focusing on immediate goals becomes critical.
• Qualitative vs. Quantitative Metrics: Success metrics are key to decision-making, and even qualitative decisions should be supported by some form of data.
• Leadership Messaging: Leaders need to ensure that directives across departments don’t conflict, as this can cause operational inefficiencies.
• Learning from Experience: Prita advises young leaders to build diverse support systems to balance different perspectives before making key decisions.

Resources:

Prita Kumar on LinkedIn

Winnie da Silva on LinkedIn I Website

What if the decisions you make as a leader are only addressing half the problem? In this episode of Transformative Leadership Conversations, I explore the hidden complexities beneath the surface of leadership challenges and how understanding those deeper issues can lead to more effective decision-making. I talk about the importance of not just focusing on what’s immediately visible but also considering the less obvious factors that might be driving the situation. By adopting a more thoughtful, strategic approach, leaders can avoid impulsive reactions and create more sustainable solutions.

Key Points:

• The Iceberg Analogy: Most of a problem’s complexity is hidden below the surface, just like an iceberg. As a leader, you need to be curious and dig deeper to uncover the real issues before jumping to conclusions.
• Decision Fatigue: Decision-making can be exhausting, especially after a full day of thinking and problem-solving. I discuss how prioritizing decisions and building routines can help you stay sharp and avoid burnout.
• Cognitive Switching: While switching between tasks can sometimes inspire creativity, too much of it can drain your mental energy. I share tips on grouping similar tasks and minimizing digital distractions to stay more focused and productive.
• The Power of Routine: Establishing a consistent decision-making routine can streamline your thought process and free up mental energy for bigger issues.
• Anticipating Hidden Challenges: Leaders must look beyond the surface of any problem, anticipating and addressing the unseen obstacles that can affect the outcome.
• Effective Decision-Making: Clear and structured decision-making processes aren’t just for you—they help keep your team on the same page and reduce confusion. I talk about how to communicate decisions effectively and ensure alignment across your organization.

Resources

Winnie da Silva on LinkedIn

Books mentioned:

- The Decision Book: Fifty Models for Strategic Thinking by Mikael Krogerus and Roman Tschäppeler

- Thinking, Fast and Slow by Daniel Kahneman

What if your relationship with work is fundamentally shaping your career decisions? In this episode, I speak with Dr. Nayla Bahri, an executive coach and co-host of The Inside Job Podcast. Nayla is dedicated to helping individuals and teams build thriving relationships with work, collaborating with leaders from startups to renowned organizations like Apple, Google, and the Federal Reserve Bank of NY. With her extensive experience as a former Dean of Students at Columbia Business School, she combines research with human-centered learning to empower clients in leading with impact, resilience, and clarity. We talk about the differences in how men and women approach career pivots and the deeper insights into creating a healthy relationship with work. We explore the importance of self-awareness and the internal work necessary for effective leadership.

• Gender Dynamics in Career Pivots: Insights from Nayla's research on how men and women perceive their career transitions differently.
• Fear and Safety in the Workplace: The impact of feeling unsafe in your job and how it influences decision-making.
• Curiosity-Driven Coaching Approach: Nayla discusses the importance of engaging in both inner and outer work to achieve career satisfaction.
• Humor in Leadership: The role of lightheartedness and humor in fostering a positive work environment.
• Leadership Reflection: How personal beliefs about work affect leadership styles and the environment created for teams.

Resources:

Dr. Nayla Bahri on the web | LinkedIn I Substack (Newsletter) I Instagram I Inside Job Podcast

Winnie da Silva on the web | LinkedIn

Ever wondered how you can turn your career dreams into reality? In this episode of Transformative Leadership Conversations, host Winnie da Silva sits down with career coach Maggie Mistal to explore how aligning your work with your passions can transform your life. Maggie Mistal, a certified life purpose and career coach and author of the Amazon #1 New Release Are You Ready to Love Your Job?, shares her own transition from the corporate world to coaching and reveals her method for career fulfillment through three stages: soul search, research, and job search. With extensive experience helping individuals transition into their ideal careers, Maggie has guided thousands through inspiring retreats and individual sessions, and her expertise is sought after by top corporations and featured in major publications like The New York Times and Forbes.com.

You’ll hear them talk about:

• Career Transition Insights: Maggie discusses her journey from corporate life to coaching and the importance of aligning work with passion and purpose.
• Three Key Stages: Maggie outlines her method for career fulfillment, focusing on:
• Soul Search: Identifying personal values and passions.
• Research: Investigating career options and networking.
• Job Search: Implementing strategies to secure desired roles.
• Practical Advice: Emphasis on the importance of research and networking in career transitions.
• Real-Life Success: Maggie shares a success story of a young client who transitioned to a fulfilling career in library science.
• Dynamic Career Management: The discussion highlights how ongoing soul searching, research, and networking can continually shape and improve your career.
• Upcoming Career Retreat: Maggie announces her cruise-based career retreat in April 2025, offering intensive career coaching and unique experiences.

Maggie Mistal on the Web | LinkedIn I Instagram I Facebook

Winnie da Silva on LinkedIn

Are you contemplating a career change but feeling uncertain about taking the leap? In this episode, Winnie explores the evolving nature of work and the increasing prevalence of career pivots. Sharing her own journey from social work to corporate training and consulting, she demonstrates how embracing these transitions can lead to unexpected and fulfilling opportunities. Through compelling statistics and inspiring stories of figures like Vera Wang and Benjamin Franklin, Winnie underscores that career changes are not only normal but can also be transformative. Tune in to discover how to navigate your own career evolution with confidence and curiosity.

Key Points Discussed:

•             Embracing Career Pivots: Winnie emphasizes that career pivots are a normal and valuable part of professional life, encouraging listeners to embrace them as opportunities for growth rather than obstacles.

•             Personal Career Journey: Winnie shares her own experience of shifting from a career in social work to roles in corporate training and consulting, highlighting the importance of following one’s passion and experimenting with new roles.

•             Statistics on Career Changes: The podcast presents statistics showing that the average person will hold numerous jobs and change careers several times over their lifetime, reflecting the dynamic nature of the modern work landscape.

•             Inspiring Stories: Winnie recounts the career transformations of notable figures like Vera Wang and Benjamin Franklin, illustrating how significant career changes can lead to remarkable success.

•             Advice for Career Transitions: Winnie offers practical tips for managing career pivots, including leveraging relationships, exploring new interests, experimenting with skills, and being open to change.

Resources:

Winnie da Silva on LinkedIn

Can ensuring your team feels valued and supported be a tool to boost productivity? In this episode, Kim Lerner and host Winnie da Silva explore how hospitality principles, such as empathy and personalized recognition, can profoundly impact team culture and leadership effectiveness. Kim shares her unique experiences integrating these principles into her leadership approach, demonstrating how they can foster stronger team connections and drive organizational success.

You will hear them talk about:

• Empathy in Leadership: Understanding and addressing the emotional needs of team members to build trust and morale.
• Personalized Recognition: Tailoring recognition and appreciation to individual team members to enhance their engagement and satisfaction.
• Balancing Hospitality and Leadership: Navigating the balance between fostering a supportive environment and maintaining high performance standards.
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Practical Strategies or Tips:

• Foster Empathy: Actively listen to your team’s concerns and needs, showing genuine care and understanding to build stronger relationships.
• Personalize Recognition: Use specific, personalized gestures of appreciation to make team members feel valued and motivated.
• Manage Stress with Hospitality: Apply hospitality principles to maintain composure and support others during high-pressure situations, enhancing overall team resilience.
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Expert Insights or Upcoming Content Teasers:

• Kim Lerner’s Experiences: Kim shares her journey of integrating hospitality practices into leadership, highlighting how these approaches transformed her team dynamics and personal effectiveness.
• Future Discussions: Upcoming episodes will feature additional insights from leaders who have successfully applied hospitality principles, providing further strategies for enhancing team culture and leadership effectiveness.
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Resources:

Winnie da Silva on LinkedIn

Kim Lerner on LinkedIn

Can a leadership approach grounded in hospitality transform your organization's customer interactions and internal dynamics? In this episode, David Cocchiara and host Winnie da Silva discuss how principles of hospitality—like genuine accountability and composure under pressure—can significantly enhance leadership effectiveness and customer satisfaction. They explore why these seemingly simple strategies are challenging to implement and how they can make a profound difference in fostering positive relationships and achieving business success.

Key Concepts or Tools Introduced:

• Authentic Accountability: Taking responsibility for mistakes and addressing them with honesty and promptness.
• Stress Impact on Leadership: How high-stress environments can negatively affect leadership quality and team interactions.
• Embracing Hospitality: Applying hospitality principles to leadership to create supportive and effective work environments.

Practical Strategies or Tips:

• Own Your Mistakes: Acknowledge and correct errors to maintain trust and satisfaction, as demonstrated with the "blue shirt" example.
• Maintain Composure: Learn from leaders who manage stress effectively and try to keep calm under pressure to positively influence team dynamics.
• Focus on People: Prioritize understanding and addressing the needs and motivations of team members to foster a supportive work culture.

Expert Insights or Upcoming Content Teasers:

• David Cocchiara’s Experience: Insights from David’s experiences in high-pressure environments and how he learned to maintain composure and hospitality in leadership.
• Future Episodes: Upcoming discussions with industry experts like Kim Lerner, who will offer additional perspectives on integrating hospitality into leadership practices.

Resources:

Winnie da Silva on LinkedIn 

David Cocchiara on LinkedIn