Transformative Leadership Conversations with Winnie da Silva

What if the reason you're not earning what you're worth has nothing to do with your skills — and everything to do with the stories you believe about money? Are you showing up like someone who knows their value… or playing it small to keep the peace? Let’s be real — money is messy. It brings up all kinds of emotions, expectations, and unspoken rules. In this solo episode, I’m sharing something personal: my own journey around money, self-worth, and what it’s taken for me to finally feel comfortable asking for what I deserve.

This episode kicks off a new theme we’re exploring this month: Leadership & Money Mindset. If you’ve ever hesitated to ask for a raise, felt weird quoting your rates, or second-guessed your worth, this one’s for you. I’m talking through the mindset shifts I had to make (and am still making!) to move from discomfort and doubt to clarity and confidence — and how you can do the same.

You’ll hear me discuss:

• What happens when you don’t value yourself. I used to feel weird asking to be paid — like it somehow made me less sincere. But I’ve learned that when I don’t own my value, other people don’t either. That had to change.
• The early money messages that shaped me. I grew up in the Midwest, where the rule was: don’t make anyone uncomfortable — especially with money talk. That silence stuck with me for years. Maybe you can relate?
• A simple framework that helps uncover limiting beliefs. I share the Story → Behavior → Result model I use with clients to break down what's really driving your actions — and how to shift it.
• Three powerful client stories — Annie, Eleanor, and Zoe. These are women who faced real turning points in their careers — promotions, negotiations, job changes — and had to totally reframe how they saw their own value. Their courage might give you the nudge you need.
• The bigger forces that make this harder, especially for women. We’ll touch on why this issue isn’t just personal — it’s also systemic. From unpaid labor to leadership stereotypes, there’s a lot working under the surface.
• A surprisingly fun tool to explore your money mindset. I’ll introduce you to the Money Type Personality Assessment (yep, it’s free!) and share what I learned about myself as a “Visionary” with a close second of “Nurturer.”
• Five big takeaways to help you shift your mindset now. These are practical, real-world ideas you can apply — whether you're pricing a project, negotiating a role, or simply trying to stop shrinking yourself at work.

Resources

Money Type Personality Test

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

“No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal

Is your pitch holding you back more than your business idea? Are you making it easy for investors to dream the dream with you? In this episode, I sit down with Medha Agarwal, General Partner at Defy, to talk about the unique challenges founders face—especially women—when pitching their startups, securing funding, and leading through growth. She shares why too many founders unknowingly undersell their vision and how simple shifts in storytelling can make all the difference.

Medha also opens up about her own career journey, from being a founder to working in venture capital, and what she’s learned about choosing the right team, adapting in fast-moving startups, and pushing past perceived limits. We also dive into her experience as a Harvard rower and the powerful leadership lessons she’s carried from the water to the boardroom.

Whether you're a founder, thinking about launching a startup, or simply curious about what separates the best pitches from the rest, this conversation is packed with actionable insights on confidence, resilience, and strategic growth.

You'll hear us discuss:

• Why women founders struggle with selling the big picture – Medha explains that many female founders naturally emphasize what still needs to be done rather than what they’ve already achieved. Investors need to see the vision and the opportunity, not just the challenges ahead.
• The subtle shift that makes a pitch stronger – Instead of pointing out gaps or weaknesses, founders should frame their journey as momentum. Investors want to be inspired—help them see how they can be part of something big and inevitable.
• The underestimated importance of flexibility in startups – Too often, people transitioning from corporate jobs to startups focus on titles and initial responsibilities. But in a fast-growing company, your job will change drastically every six months. The real key to success is choosing the right company and founder rather than clinging to a specific role.
• What makes a startup worth joining – Medha stresses that it's better to join a company where you believe in the founder’s vision and leadership style, even if the role isn’t perfect. A rising tide lifts all boats—if the company succeeds, so will your career.
• How rowing taught her to lead and collaborate – Rowing is the ultimate team sport, where trying to stand out individually slows the whole boat down. The same applies in startups—success comes from alignment, trust, and moving in sync with the team.
• The reason she prefers working behind the scenes – Medha admits she’s uncomfortable with the spotlight on herself and much prefers helping others shine. This mindset makes her a stronger investor and advisor—she’s fully focused on helping founders succeed, not chasing personal recognition.

Resources

Medha Agarwal on LinkedIn | Defy

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

"My role is catching the ideas and making them happen." – Stephanie Unwin

Is your leadership moving forward, or are you just keeping busy?

In the fast-paced world of executive leadership and entrepreneurship, it can feel impossible to carve out time to think strategically. But what if making space for reflection isn’t a luxury—it’s the key to unlocking long-term success? In this episode of Transformative Leadership Conversations, I sit down with Stephanie Unwin, a seasoned executive and business leader, to explore how prioritizing strategic thinking not only makes you a stronger leader, but also helps you steer your company toward sustainable growth.

Stephanie opens up about the importance of deliberately carving out time for reflection, recharge, and deep thinking—ensuring that leadership isn't just about constant action but also about intentional decision-making that shapes the future of the business.

You'll hear us discuss:

• Why carving out time to think is not a “nice to have”—it’s a leadership necessity. As an executive, it’s easy to get swept up in the whirlwind of daily demands—meetings, emails, and urgent decisions that take up most of your day. However, without setting aside dedicated time to reflect, refine strategy, and gather your thoughts, leaders risk losing sight of the bigger picture.
• The secret to balancing high-energy execution with moments of clarity. Leading a company often feels like an unending sprint. While constant action and execution are important, Stephanie explains how never taking a step back to pause and think can lead to burnout, decision fatigue, and reactive leadership.
• Why founders and executives must stay aligned on vision, values, and risk-taking. Whether you’re working for a founder or running a startup yourself, one of the most critical components of leadership is alignment. Stephanie dives deep into why executives must ensure that their vision, values, and approach to risk-taking are in sync with the founders or leadership team.
• How to navigate change without losing sight of the bigger picture. The business world is in a constant state of flux—markets shift, technologies evolve, and customer demands change. Leaders who resist change or get bogged down by every shift risk falling behind. Stephanie shares her approach to staying agile, adapting to changes, and continuously innovating without compromising the company's core mission and values. .
• The underestimated power of trusting your team and leveraging their insights. No leader has all the answers, and the most effective leaders are those who recognize the importance of collective intelligence. Stephanie highlights how fostering a culture where team members feel empowered to share ideas, challenge assumptions, and contribute to strategic discussions can greatly enhance decision-making.

Resources

Stephanie Unwin on LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

What makes some founders incredible leaders—and others impossible to work with? They are visionaries, but are they always great leaders? Founders bring passion, vision, and drive, but they can also be intense, stubborn, and relentless. Working with them isn’t just about executing their vision—it’s about knowing when to support, when to challenge, and how to scale alongside them. So how do you do that effectively?

In this episode of Transformative Leadership Conversations, I dive into what makes founders tick, the challenges they face, and how you can be a strategic partner in their success. Whether you work for, with, or invest in a founder, understanding their mindset is key to building a strong and successful relationship.

You’ll hear me discuss:

• The surprising data behind founders—Forget the stereotype of the young tech genius. The average founder is older than you might think, and startups with multiple founders tend to outperform solo-led businesses. I break down what the numbers actually tell us about who succeeds and why.
• The four founder archetypes—Inventors generate endless ideas but struggle with execution. Drivers push forward with sheer determination but risk burnout. Builders create structure and scalability but may resist change. Guides lead with vision and culture but can be too hands-off. I’ll explain how to work with each type effectively.
• How to challenge a founder without clashing—The best partners don’t just follow orders; they push founders to grow. I share strategies for helping founders see blind spots, make better decisions, and scale successfully—without stepping on toes.
• The pitfalls founders face (and how to help them avoid them)—From burnout to hiring mistakes to emotional attachment that clouds judgment, many founders struggle to transition from startup hustle to sustainable leadership. I’ll highlight key risks and how you can help navigate them.
• What makes working with founders so exciting (and tough)—Founders move fast, take risks, and embrace uncertainty. That energy is contagious, but it can also be exhausting. I’ll share what I love about working with founders—and the biggest challenges to watch for.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

“Leadership without courage isn't leadership at all, but courage without integrity is dangerous.’’ - Winnie da Silva

What if your fear was the key to unlocking your greatest leadership potential? In this episode of Transformative Leadership Conversations, I explore the often-overlooked power of fear in leadership. Fear is something all leaders face, but it's not the fear itself that defines us—it's how we respond to it. You’ll hear me discuss how we can transform fear from a roadblock into a powerful catalyst for courageous leadership. The question isn’t whether you’re afraid, it’s what you choose to do in the face of that fear.

As we navigate these turbulent times, it’s more important than ever to lead with courage, not just for yourself but for your team. Fear will always be a part of leadership, but what if you could choose courage instead of being paralyzed by fear?

You’ll hear me discuss:

• The Neuroscience of Fear: I break down how your brain responds to fear and why your body treats psychological threats just like physical ones. I’ll explain how your brain’s stress response can hijack your decision-making and what this means for leaders in high-pressure situations.
• The Role of Courage in Leadership: Courage isn’t about eliminating fear—it’s about navigating it. I'll explain why leadership without courage isn't really leadership at all, and why courage without integrity is dangerous. Courage is a skill, not a trait, and it’s essential for effective leadership, especially in times of uncertainty and fear.
• The Brain’s Built-in Mechanism for Courage: Neuroscience reveals that our brains are wired to react to fear, but the good news is we can override that natural response. I'll show you how activating your prefrontal cortex allows you to make better decisions, even when fear is present. Courage isn’t the absence of fear—it’s the ability to act in spite of it.
• Whistleblowing as an Act of Courage: Using the example of Stephen May, a whistleblower from Purdue Pharma, I’ll discuss how standing up against unethical practices takes immense courage, even when the cost is high. You’ll hear how speaking truth to power can lead to transformational change, even when the path isn’t easy or well-received.
• Practical Strategies to Cultivate Courage: Finally, I’ll offer practical steps to help you develop and strengthen your own courage. From identifying where fear is holding you back to taking small, intentional steps, I’ll guide you on how to confront fear head-on and train yourself to be a braver, more effective leader.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

"The old model of leadership, commanding, dominating, and never admitting failure, is outdated, and more importantly, it's ultimately ineffective." - Winnie da Silva

Is humility the secret weapon some leaders are overlooking? In today’s fast-paced world, we’re taught to believe that the most successful leaders are the loudest, the boldest, and the most aggressive. But what if humility, often seen as a weakness, is actually the missing ingredient to becoming a more effective and respected leader? In this episode of Transformative Leadership Conversations, the second one in the Neglected Leadership Characteristics series, I’m challenging the traditional view of leadership and showing how humility can drive better business results, strengthen relationships, and foster a culture of trust and innovation.

You’ll hear me discuss:

• Why humility isn’t weakness: I unpack how humble leaders aren’t passive or pushovers, but confident, decisive individuals who are willing to take a stand even when it’s unpopular. Humility doesn’t mean avoiding conflict—it means making thoughtful, informed decisions with integrity.
• The power of reframing humility: Today, humility is often seen as outdated or even embarrassing, especially in industries that reward aggressive self-promotion. I’ll explore how rebranding humility as a strength can help leaders build stronger teams and make better decisions in uncertain times.
• The critical difference between humility and arrogance: Arrogance can alienate teams and cloud judgment, while humility creates trust and respect. I’ll share how embracing humility can lead to higher engagement, stronger relationships, and more creative solutions in the workplace.
• How humility fuels innovation: I’ll dive into how humble leaders actively seek out diverse perspectives, encourage experimentation, and admit they don’t have all the answers. In a world that’s constantly changing, this mindset is key to staying ahead of the competition and creating lasting impact.
• Practical tips for embracing humility in your leadership style: It’s not enough to just talk about humility—I’ll share actionable strategies you can use to incorporate humility into your daily leadership practice, such as seeking feedback, admitting mistakes, elevating others’ contributions, and staying grounded despite success.
• Why humility might be the antidote to today’s leadership challenges: From disorientation to fear and uncertainty, we’re living in a time when traditional approaches to leadership are failing. I’ll explain how humility could be the solution to navigating these complex challenges while building a stronger, more resilient organization.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

"Encouraging disagreement strengthens decision-making, challenges blind spots, and creates an environment where people feel heard." - Winnie da Silva

What if avoiding disagreement is actually holding you back? Most of us instinctively avoid conflict. We’re taught that disagreeing can damage relationships, create tension, or make us look difficult. But what if I told you that the way we approach disagreement could be the key to making better decisions, building stronger teams, and gaining real influence? The truth is, the most successful people don’t run from disagreement—they master it. In this episode of Transformative Leadership Conversations, I explore how to turn conflict into a tool for growth rather than a source of frustration. I break down why disagreement is not the enemy, why avoiding it can be more damaging than facing it, and how the best leaders use it to their advantage.

You’ll hear me discuss:

• Why avoiding disagreement is riskier than facing it – The hidden dangers of keeping quiet and why people often regret not speaking up more than they regret engaging in a debate.
• How Abraham Lincoln turned political rivals into trusted allies – A look at his Team of Rivals approach and how bringing opposing voices together led to better decisions.
• The difference between arguing to win vs. arguing to learn – Why treating disagreement as a battle is the fastest way to lose credibility, and what to do instead.
• Why true influence isn’t about power—it’s about how you disagree – The people who hold the most influence aren’t necessarily the ones in charge, but the ones who challenge ideas the right way.
• The 3 common ways people handle disagreement—and the one that actually works – Do you avoid, attack, or adapt? Understanding these patterns will help you shift toward more productive conversations.
• How to make disagreements feel less personal and more productive – A simple mindset shift that reduces defensiveness and keeps the conversation focused on solutions.
• Practical techniques for disagreeing without damaging relationships – Real strategies to express your point of view while still keeping mutual respect intact.
• How to be persuasive without being confrontational – The key to making people listen to you without raising your voice or shutting them down.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack I Email - [email protected]

"Motivation starts with identity—when you believe in the story you’re telling yourself, the actions follow." - Nikhil Paul

Is it possible to lead with passion and effectiveness if you no longer feel connected to the business you're running? In this engaging conversation, I have with leadership coach Nikhil Paul, he dives deep into the heart of leadership, self-reflection, and sustainable business practices. Nikhil emphasizes the importance of personal connection to the work and the culture, asking leaders to reflect on their commitment to their businesses. He also sheds light on how companies, especially startups, often overlook the foundational cracks that could undermine their success in the long term. Drawing on his expertise, Nikhil offers a framework to help leaders assess their organizations' true sustainability and overall health.

Nikhil also shares his 5 Pillars of Motivation—a guide to scaling a business without losing its soul. These principles are designed to help organizations grow in a way that maintains their core values and sense of purpose.

Hear us discuss:

• Leadership self-reflection: The importance of checking if you still love your business and the work you're doing. Nikhil reveals how leaders can become disconnected from their own mission and the impact it has on company culture.
• Assessing business sustainability: What happens if you step away from your company? How defensible is your business? Nikhil challenges leaders to think about their company's stability and operational health in their absence.
• Growth versus foundational strength: Why simply scaling the business without addressing the root issues can eventually lead to problems down the line. Growth can often mask underlying weaknesses, and businesses may struggle when that growth slows down.
• The 'elephant in the room' approach: Nikhil discusses how acknowledging discomforts or dissonance early on can prevent larger issues from festering and undermining leadership.
• Ruthless prioritization: In today's fast-paced business world, Nikhil emphasizes the importance of focusing on what truly matters, ensuring that leaders don't get lost in tasks that aren't adding value to the business.
• Culture and leadership dynamics: The critical link between a leader's connection to the business and the health of the team or organization. Without alignment at the leadership level, the overall culture and direction are at risk.

5 Pillars of Motivation

1. Connect with our cult customers, the small group who needs us and loves us the most. Focus on identifying and nurturing the loyal core group of customers who truly resonate with your mission and product.
2. Focus on doing work our people love doing so that they can hone their craft. Creating an environment where employees are passionate about their work ensures continuous growth, skill development, and overall satisfaction.
3. Give each person their little kingdom to run & help them with it. Empower your team by giving them ownership and responsibility for their areas while providing support for their success.
4. Forge a real tribe for people to belong to. Building a community within your organization creates a sense of belonging, fostering loyalty, and helping individuals feel connected to a greater purpose.
5. Find a way to help save the world in our own small way. Inspire your team by aligning the company’s mission with a higher cause, even if it’s a small step, to make a positive impact in the world.

Read more about Nikhil's Kind Cult Empire framework in his blog.

Resources

Books mentioned by Nikhil:

• Start with Why by Simon Sinek
• The Five Dysfunctions of a Team by Patrick Lencioni
• Leaders Eat Last by Simon Sinek
• Good to Great by Jim Collins
• The Hard Thing About Hard Things by Ben Horowitz

Nikhil Paul on LinkedIn | On the Web | Blog | Email: [email protected]

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

"When you align individual motivation with the broader mission, that’s when magic happens and teams thrive.” - James Thorman

What does it take to lead a team with purpose, ignite individual motivation, and build a thriving, high-performing culture? In this episode of Transformative Leadership Conversations, James Thorman, a seasoned leader with a wealth of experience from his time at A Place for Mom and other roles, joins me to dive deep into the core elements of effective leadership. He explains how understanding the unique motivations of individuals within a team is crucial for achieving collective success. Through thoughtful leadership strategies and a commitment to aligning personal and organizational goals, James explores how teams can be nurtured to reach their full potential. He shares valuable insights into building a team culture that fosters growth, collaboration, and high performance. From senior leadership lessons to practical tools for day-to-day team dynamics, James provides a comprehensive look at what it takes to lead a motivated team that is driven by both personal satisfaction and the company's mission.

Hear James and I discuss:

• Understanding Motivations: James reflects on an early lesson in his career, learning from his colleague Tatiana that people’s motivations differ and aren’t always aligned with our own. He emphasizes how crucial it is to understand those differences to unlock the full potential of your team.
• Aligning People with Purpose: As leaders, it’s vital to connect personal motivations with the greater mission of the organization. James elaborates on the importance of ensuring that individual goals align with company goals. When people are invested in the purpose and mission, their drive to succeed becomes much stronger.
• The Importance of Company Ethos: As you rise through the ranks, James explains the need to deeply understand your company’s ethos and what it will take to achieve its goals. If leaders don’t understand the mission, they risk setting their teams up for failure. He underscores how integral it is to create an environment that reflects and supports this ethos.
• Effective Leadership Strategies: James talks about some of the specific leadership practices he has found most effective in motivating teams. From setting the right tone at the top to helping employees identify what excites them, he discusses actionable insights on how to get the best out of your team.
• The Role of the Senior Leader: James shares his thoughts on the responsibilities of senior leaders in fostering team success. He talks about how understanding the broader company mission and helping employees connect to that mission is one of the keys to motivating a high-performing team.
• Building High-Performing Teams: One of the most rewarding aspects of leadership, according to James, is when everything clicks into place—when the team starts thriving, collaborating effectively, and engaging with each other. He talks about the iterative process of building a successful team, where learning and growth are constant, and how critical it is to have the right mix of motivation, mission alignment, and structure.
• Creating an Environment for Success: As much as individual motivation is important, James emphasizes that creating the right structure, cadence, and environment is just as critical. With the right team fit and the appropriate resources, teams are more likely to thrive in the long run.
• The Importance of Explicit Communication: James and Winnie discuss how senior leaders can create more effective teams by engaging in open, explicit conversations about motivation. They explore how asking team members what excites them or where they find their energy can lead to deeper, more productive discussions that help leaders tailor roles and expectations to each person’s strengths.
• The Long-Term Rewards of Team Alignment: James reflects on the ultimate payoff when everything aligns—motivated individuals, aligned company goals, and a culture that supports growth and high performance. When this happens, teams not only succeed but thrive in ways that benefit both individuals and the organization as a whole.

Resources

James Thorman on LinkedIn | A Place for Mum website

Winnie da Silva on LinkedIn | On the Web | Substack I Email - [email protected]

"Leaders can't motivate people—and nor should they. But what you can do is foster an environment where intrinsic motivation can thrive." - Winnie da Silva

What if I told you that motivating your team isn’t your job? It sounds counterintuitive, right? As a leader, your instinct is to inspire your team to perform at their best—but real, lasting motivation comes from within. In this episode of Transformative Leadership Conversations, I challenge the traditional view of leadership by flipping the script: instead of motivating your team, focus on creating an environment where intrinsic motivation can thrive. Through meaningful one-on-one conversations, leaders can help team members clarify what drives them, align work with their passions, and ultimately improve engagement and performance. Motivation isn’t a one-size-fits-all approach—it’s personal, dynamic, and deeply impactful when done right.

Listen to me talk about:

• Motivation is Personal - What motivates you may not motivate your team. That’s okay—and understanding this is the first step to unlocking better performance and engagement.
• Leaders Can't Motivate People—And They Shouldn’t - Your role as a leader is not to "motivate" others. Instead, it's about creating the conditions where intrinsic motivation can flourish.
• Meaningful Conversations Drive Engagement - When was the last time you had a one-on-one conversation with a team member about what truly drives them? These conversations are key to building trust, uncovering motivators, and reigniting engagement.
• Intrinsic Motivation Matters More Than Perks - People are most engaged when their work aligns with intrinsic motivators like autonomy, purpose, and progress—not just external rewards like paychecks or promotions.
• Shared Responsibility: Team Members & Leaders - Motivation is a two-way street. Team members must reflect on what they want, communicate openly, and take initiative, while leaders must facilitate clarity, encourage ownership, and provide support.
• Practical Steps for Leaders:

I share a step-by-step guide for holding motivational one-on-one conversations:

• Clarify what’s important – Help team members articulate what matters most to them.
• Define the gaps – Identify where their current experience falls short of their desires.
• Problem-solve together – Collaborate to find actionable ways to align work with motivators.
• Powerful Reflective Questions for One-on-Ones - Here are six questions you can ask to help your team members uncover what drives them:
• At this point in your life and career, what are the two to three most important things you want from your job?
• On a scale of 1 to 10, how satisfied are you with your current job? What would it take to get closer to a 10?
• What parts of your job do you enjoy the most? The least?
• If you could change your job to make it more rewarding, what changes would you make?
• What’s one thing you’re not getting enough of from your work?
• What have you noticed about how your motivators have evolved over time?

Winnie da Silva on LinkedIn | On the Web | Substack I Email - [email protected]