Cover Image for Friday Forums: The Art of Asking

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Friday Forums: The Art of Asking

StartupExperts Events

Zoom

Past Event

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About Event

A practical workshop on curiosity, clarity, and courageous conversations

Most people think they struggle with asking because they don’t know what to say.

In reality, they struggle because asking exposes uncertainty, truth, and the possibility of hearing “no.”

The Art of Asking is a one-hour interactive workshop for professionals who want to communicate more clearly, build trust faster, and navigate high-stakes conversations without avoidance or pressure.

At its core, asking is not a sales tactic – it’s a relational skill. The quality of your questions determines the quality of your relationships, decisions, and outcomes.

Whether you’re selling an idea, leading a team, coaching a client, or advocating for yourself, the ability to ask well is one of the most powerful – and underdeveloped – skills in professional life.

In this session, Robin Zander explores why we under-ask or avoid asking altogether – and how each pattern is a form of resistance. Participants will learn how to replace anxiety and guesswork with intentional curiosity, clear boundaries, and good intent.

Participants will learn:

Why asking questions is the fastest way to build trust and rapport
The different types of questions—and how each shapes a conversation
How to stay curious under pressure instead of becoming passive or defensive
How to ask questions that clarify fit, surface truth, and move conversations forward
How to make clean, direct asks without manipulation or urgency

Through short stories, a practical framework, and guided exercises, participants will practice:

Asking better questions in real time
Clarifying intentions and boundaries before important conversations
Recognizing when a question builds connection—and when it creates distance
Making the ask once the truth is clear, without trying to control the outcome

The Art of Asking is designed for thoughtful professionals who want to think more clearly, communicate more honestly, and engage others with respect and confidence.