In this candid and wide-ranging conversation, veteran banking leader Bob shares hard-earned wisdom from over 17 years of running a successful asset-based lending group at Wintrust. With a people-first mindset and a leadership style rooted in collaboration, Bob explains how hiring talented individuals—often smarter or more specialized than himself—has laid the foundation for a high-performing, loyal team. Nearly all team leaders under his guidance have risen through the ranks internally, proving the long-term power of promoting from within and fostering growth through mentorship and trust.

But leadership doesn’t stop at staffing. Bob outlines how transparency, clear expectations, and consistent communication—internally and with clients—have been key to building enduring relationships. He emphasizes the critical moments that truly test a lender-client relationship: not during sunny market upswings, but in challenging cycles like COVID, trade disruptions, or raw material shortages. These inflection points reveal character and commitment on both sides, and Bob’s team strives to be proactive, planning months in advance, rather than reacting at the last minute.

For Chicago-based lenders and business leaders, Bob also shares insights into the city’s unique financial landscape and the additional responsibility that local institutions bear in preserving and growing client relationships in an increasingly globalized market.

This episode is packed with wisdom on leadership, succession planning, team development, and client trust—all built on a foundation of honesty, humility, and mutual respect. Whether you’re in finance, consulting, or leading a growing business, Bob’s emphasis on hiring great people, planning for tomorrow, and earning trust through communication will resonate deeply. This isn’t just good banking—it's great business leadership.

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