PIE-Cast

Why Great Advisors Ask Better Questions with Mark Cheshire

Profitable Ideas® Exchange

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0:00 | 18:18

Andi Baldwin and Jacob Parks sit down with Mark Cheshire to explore what truly defines a great rainmaker—and why business development skills can be developed, not just inherited.

Drawing on decades of experience as a CEO and client of professional services firms, Mark shares what he looked for when deciding which advisors earned his trust. Through real-world stories, he unpacks the skills that matter most, the role preparation and empathy play in client relationships, and why asking better questions can set advisors apart.

The conversation also touches on how COVID disrupted skill development, what younger professionals can do differently today, and the habits Mark consistently saw in the most effective advisors.