“When you can show up in service of someone else’s work ahead of your own, it stops feeling transactional.” - Carly Valancy

Networking has become one of the most dreaded words in professional life. It feels transactional, awkward, and exhausting. But in a world increasingly driven by AI and digital communication, real human connection may be more valuable than ever.

In this episode, I sit down with Carly Valancy, founder of Reach Out Party, to talk about her philosophy of “anti-networking” - a more human, generous, and courageous way to build relationships and create opportunity.

You’ll hear us discuss:

• Why traditional networking feels so uncomfortable and how to approach it differently
• Carly’s framework for writing “unignorable” messages that people actually respond to
• The hidden fears that stop most people from reaching out in the first place
• Why reaching out is one of the highest leverage things you can do for your career
• How planting seeds for your future self can create opportunities years later
• The unexpected internal confidence shift that happens when you consistently put yourself out there
• Why meaningful human connection is becoming a major differentiator in an AI-driven world

Resources

Carly Valancy on Website | Reach Out Party | Tether | Substack | LinkedIn | Momentum Growth Plan

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

“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?”