Visual Thinking to Communicate with Clarity: Bill Shander

How to Ask Better Questions Without Saying "Why?" Stakeholder Whispering: Secret to Better Communication

Episode 262 (Bill is based in New Mexico)

In this conversation with Bill Shander we explore:

• How to uncover what your stakeholders really need—beyond what they ask for

• Why your first idea is often just an automated response

• How to apply the Socratic method to guide people toward their own insight

• Why asking “why” directly can feel hostile, and what to say instead

• The power of “chunky segmentation” to clarify vague communication

• How to balance divergent and convergent questions to get to the truth

• What aporia means—and why a little confusion leads to breakthrough thinking

• Why your visuals must reflect meaning, not just style

• When and how AI can support visual storytelling and insight

• Why it’s crucial to practice stakeholder whispering on yourself first

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About our guest, Bill Shander:

Bill has been teaching data storytelling and visualization for about 10 years for clients around the world and on on Linkedin Learning.

He is the author of "Stakeholder Whispering: Uncover What People Need Before Doing What they Ask"

You can find his book here: Stakeholder Whispering

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Key lessons from this conversation:

1. Most stakeholders don’t know what they really need.

• Insight: Stakeholder requests are often surface-level assumptions, not true needs. Your job is to dig deeper.

2. Your first idea is usually just an automated response.

• Insight: Pause before acting. The first idea might be convenient, but often lacks strategic depth.

3. Use Socratic questioning to help people uncover their own truth.

• Insight: Ask layered questions to lead stakeholders into self-awareness rather than handing them answers.

4. Avoid hostile “why” questions—ask with curiosity instead.

• Insight: Reframe your language: say “Tell me more about…” instead of “Why did you do that?”

5. Translate ambiguous requests using “chunky segmentation.”

• Insight: Break vague statements (e.g., “We do masterclasses”) into discrete elements to clarify meaning.

6. Push stakeholders into a state of puzzlement (aporia).

• Insight: Confusion can be a productive step toward clarity—help stakeholders get there.

7. Visuals are communication tools—not just decoration.

• Insight: Choose visuals based on the real message, not just what’s easy to draw.

8. AI is a helpful partner, but only if you know your message.

• Insight: Tools like AI are only effective after you’ve clarified your intent and message.

9. Leaders should hire people who push back.

• Insight: Order-takers may be efficient, but real innovation comes from collaborators who challenge assumptions.

10. Practice stakeholder whispering on yourself first.

• Insight: Self-questioning sharpens your ability to lead others through discovery and insight.

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Your Intended Message is the podcast about how you can boost your career and business success by honing your communication skills. We’ll examine the aspects of how we communicate one-to-one, one to few and one to many – plus that important conversation, one to se