“Leadership growth happens when we begin practicing new behaviors in the real world.” - Winnie da Silva

Some of the biggest leadership breakthroughs don’t come from massive reinventions. They come from one small shift repeated consistently over time.

In this episode, I’m digging into why so many leaders get stuck thinking about growth instead of actually practicing it and why tiny experiments might be one of the most powerful tools for real leadership development.

You’ll hear me discuss:

• Why leaders often get trapped thinking about growth instead of practicing new behaviors
• How tiny experiments reduce overwhelm and make meaningful change feel more achievable
• Why confidence is usually built through action and repetition, not before it
• The power of small, consistent leadership behaviors over dramatic transformation
• How reflection frameworks like “plus, minus, next” help create sustainable growth
• What I learned from running my own public leadership experiment around strategic thinking
• Why experimentation, adaptability, and continuous learning are becoming essential leadership skills today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Tiny Experiments in Leadership Thinking episode - December 2025

“Leadership at scale isn’t about having all the answers—it’s about drawing out other people’s thinking.” - Winnie da Silva

Why do so many leaders feel like they have to carry all the answers, and what is it actually costing them?

In this episode, I unpack one of the most overlooked leadership tools: asking better questions. I share why constantly jumping in with solutions can quietly limit your team’s thinking, and how shifting toward thoughtful, open-ended questions can completely change the way you lead. It doesn’t mean stepping back or losing authority, but it does elevate the quality of conversations, decisions, and ownership across your team.

You’ll hear me discuss:

• Why having all the answers can actually hold your team back
• How asking questions creates ownership instead of dependency
• The connection between inquiry and reducing defensiveness
• How better questions uncover hidden risks, assumptions, and blind spots
• Why leaders who ask more questions tend to make stronger decisions
• How questions build trust and increase accountability across teams
• Simple, real-world questions you can use in conversations starting today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Example Questions: Understanding someone’s thinking

• “That’s an interesting point. Tell me more about what you're thinking.”
• “When you say X, what does that mean to you?”
• “What would need to be true for this to work?”
• “What do you care most about in this situation?”

Collaboration and partnership

• “How might we best partner together on this?”
• “What role would you like me to play here?”
• “What decision do you need from me today?”

Feedback conversations

• “What feedback do you have for me?”
• “What’s hard to tell me?”
• “What are we not talking about that we probably should be?”

Vision and goals

• “If you and your team could only achieve one thing this year, what would it be?”
• “What challenge, if solved, would make the biggest difference?”
• “What are your top priorities and why?”

Problem-solving and decision-making

• “What might be the root issue underneath this?”
• “What are we implicitly saying no to by saying yes?”
• “What data would change your mind?”

“The issue isn’t the strength of the idea. It’s whether it connects to what the other person cares about.” - Winnie da Silva

Why do some ideas land instantly… while others just hang in the air, no matter how well you explain them?

In this episode, I break down a simple but powerful leadership concept that can completely change how you influence others, especially when you don’t have formal authority. I share how understanding what people truly care about (their “currency”) can shift conversations, build trust faster, and help your message actually stick.

You’ll hear me discuss:

• Why strong arguments alone don’t guarantee influence
• What “currency” really means and how it shows up in everyday leadership
• How to spot what someone values based on their behavior and priorities
• Simple ways to reframe your message so it connects and lands
• How this applies to stakeholders, feedback, trust-building, and big conversations
• Why influence is less about pushing your point and more about aligning with what matters to others

Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“The goal isn’t ideas—it’s behavior change that drives business results.” - Winnie da Silva

Why do so many leadership programs fall flat even when the content is solid? I’ve seen this play out time and time again over the past two decades. It’s rarely about the quality of the program itself. It’s about what’s happening around it. In this episode, I break down the two factors that actually determine whether leadership development creates real, lasting change. I also share where things tend to go wrong.

You’ll hear me discuss:

• Why leadership development only works when both the leader and the organization are fully engaged
• The mindset shifts I consistently see in leaders who grow the fastest
• What it really looks like to apply leadership development in real time (not just learn it)
• How organizational culture and senior leadership behavior can make or break development efforts
• Why treating leadership development as a “check-the-box” exercise leads to poor results
• What needs to be in place for leadership growth to actually stick and drive business outcomes

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“In leadership, the visible problem is often just the symptom.” - Winnie da Silva

Is the problem you’re trying to solve actually the real problem or just the most obvious one?

In this episode, I unpack why so many leadership challenges don’t get resolved the way we expect, and how quickly jumping to solutions can keep us stuck in the same cycles. I share a real client story and walk through how to slow down just enough to uncover what’s really driving the issue, so you can create solutions that actually last.

You’ll hear me discuss:

• Why the visible problem is often just a symptom, not the root cause
• How pressure and urgency push us into solving the wrong thing
• The difference between surface issues and deeper organizational dynamics
• A real example of how misalignment at the top created slow decision-making
• The role of trust, expectations, and avoided conversations in team challenges
• Simple questions I use to dig deeper and challenge my own assumptions
• How pausing, gathering input, and testing solutions leads to better outcomes

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Coaching isn’t remediation. It’s acceleration.” - Winnie da Silva

Is executive coaching really just a last resort for struggling leaders… or is that completely missing the point? In this episode, I unpack one of the biggest myths around coaching and share what I actually see in my work with high-performing leaders. I explain why leadership coaching is about growth, not fixing, and why the right support at the right time can completely shift your leadership impact.

You’ll hear me discuss:

• Why coaching is often misunderstood as a performance fix instead of a growth accelerator
• What really changes when a strong leader steps into a bigger, more complex role
• How blind spots show up even for high performers and how I help uncover them
• Why reflection is something most leaders don’t get enough of (and why it matters)
• How coaching creates space to think differently, test ideas, and navigate complexity
• The difference between coaching and other tools like feedback, training, or performance management
• A real example of how one leader expanded their impact by shifting how they influence and make decisions

Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Real leadership work isn’t about fixing people—it’s about addressing root issues.” - Winnie da Silva

Are you stepping into bigger leadership… but still thinking and operating the same way?

In this episode, I break down what it really takes to grow as a leader when the pressure, complexity, and expectations all level up. I share how I work with leaders and teams, the frameworks behind that work, and why lasting change comes from mindset shifts instead of quick fixes.

You’ll hear me discuss:

• Who I work with and the types of leadership transitions and challenges they face
• Why leadership is less about industry and more about mindset and people
• What executive coaching actually looks like and how it drives real results
• Why leadership development must lead to behavior change, not just learning
• The three core areas of my work: coaching, leadership development, and team effectiveness
• How to tell if a team is truly effective (and what to look for)
• Why sustainable results come from addressing root causes, not quick fixes

Resources

Celebrating 20 Years of Transformative Leadership Episode

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Most leadership problems aren’t what they seem.” - Winnie da Silva

You might think the issue in front of you is the real problem… but what if it’s just the surface? This season, I’m shifting things a bit. Instead of longer guest conversations, I’m bringing you shorter, more focused episodes designed to help you think more clearly, challenge your assumptions, and take immediate action in your leadership. Because the truth is, most leadership challenges aren’t as straightforward as they seem, and if we don’t slow down and look deeper, we risk solving the wrong problem entirely.

In this episode, I’m setting the stage for what’s ahead and sharing why this shift matters, especially if you’re navigating complex, messy, real-world leadership situations.

You’ll hear me discuss:

• Why many leadership problems are often misdiagnosed at first glance
• What tends to sit beneath common challenges like performance issues or communication breakdowns
• How unexamined assumptions and internal narratives can quietly shape your leadership effectiveness
• Why solving only what’s visible can lead you to miss the bigger issue
• The idea that leadership isn’t about fixing people, but about addressing root causes
• How asking better questions can become your most powerful leadership tool
• What it looks like to adapt your leadership approach based on people and context
• The frameworks I use with clients to build trust, experiment, and lead more intentionally
• How this season is designed to give you practical, usable insights you can apply right away

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org