Stop Telling, Start Asking with Winnie da Silva

“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?”