Leadership, Grit, and Building a Culture of Excellence: Insights from Steve Hufford

For Steve Hufford, Senior Managing Director and Head of Investment Banking at Raymond James, it’s a combination of discipline, adaptability, and a focus on the human side of the business.

With a career that spans law, entrepreneurship, and senior leadership at a Fortune 500 firm, Steve’s journey is a masterclass in versatility and resilience. In this interview, he shares his keys to successful deal-making, advice for junior bankers, and how Raymond James builds a culture that empowers its people.

Whether you’re an analyst eager to grow or a leader seeking inspiration, Steve’s insights provide actionable lessons for every level.

From Law to IB Leadership: A Non-Linear Journey

Steve’s path into investment banking was far from traditional. He started as a lawyer, co-founded and sold businesses, and eventually joined Raymond James to build its financial technology investment banking practice.

“I’ve seen M&A from the agent’s perspective, the investor’s perspective, and the company builder’s perspective,” Steve explains. This diverse experience has given him unique insights into navigating deals and leading teams.

Today, Steve oversees a global investment banking division with 675 bankers across 25 offices, focusing on middle-market transactions ranging from $100 million to $5 billion.

The Rules of Investment Banking

Steve credits much of his success to adhering to key principles developed with his boss and partner Jim Bunn, including:

• Making calls relentlessly: “Have a call plan and reach out to potential clients every day - consistently and relentlessly.

• Listening attentively: “Understand the client’s problem before responding.”

• Being tenacious and solution-oriented: “Clients expect bankers to solve problems, not just identify them.”

“These rules aren’t just for junior bankers—they’re for everyone in the business,” Steve emphasizes.

Advice for Junior Bankers: Treat it as an Apprenticeship

Steve views the early years of an investment banking career as a critical apprenticeship period.

“Be present in the office to observe senior bankers,” he advises. “Learn soft skills like negotiation, communication, and how to ‘own the room’ in a pitch context.”

He encourages young bankers to develop grit and persistence while remaining super observant of the leaders around them. “It’s not just about technical skills—it’s about understanding what makes people tick, and then helping them reach their objectives and become successful.”

Managing and Mentoring Senior Leaders

Steve approaches his relationships with senior leaders as opportunities for mutual growth.

“Even senior bankers have areas they can work on,” he explains. He cites examples like improving organization in call planning or enhancing presentation methods. “It’s important to help them refine their approach while learning from their experience. And it’s a two-way street - a lot of times, I call them to give them some feedback, and then they return the favour, and we’re both learning and growing.”

This collaborative mindset fosters continuous development and ensures that leadership at all levels is aligned with the firm’s goals.

Importance of a Call Plan

For senior bankers, Steve emphasizes the need for a disciplined and strategic approach to client outreach.

“Call planning is critical,” he says, sharing the example of a senior banker at Raymond James, a superstar, who meticulously maps out calls, cities to visit, and objectives in a detailed spreadsheet every week.

“Reviewing these plans weekly ensures focus and alignment. Are you targeting the right clients? Should you narrow the list to make your efforts more impactful?” This level of organization not only improves productivity but also ensures that client relationships are managed thoughtfully.

Mentorship and Networking: Building Relationships Organically

Mentorship is at the heart of career development, but Steve believes it works best when it develops naturally.

“Instead of directly asking for mentorship, a young banker should just express genuine interest in a senior banker’s skills,” he suggests. “Say something like, ‘I noticed you handled that negotiation really well. Can we grab coffee so I can learn how you developed that skill?’”

This approach fosters meaningful connections while creating opportunities for growth.

Recognition: A Cornerstone of Raymond James Culture

At Raymond James, recognition isn’t an afterthought—it’s built into the firm’s DNA. Recognition practices include weekly emails highlighting closed deals; quarterly leader boards celebrating top teams; and the liberal distribution of ‘game balls’ (basketballs in RJ colours). The investment banking management team seeks to establish a culture where acknowledging the team’s wins is both consistent and robust.

“These practices make people feel good about what they’re doing here,” Steve shares. “It’s about creating an environment where people see the wins clearly, and are therefore motivated to continue to excel.”

Final Thoughts: It’s a Long Game

If Steve could give advice to his younger self, it would be to focus on the big picture.

“This is a long game,” he says. “Build a broad skillset, don’t stress over small issues, and keep everything in perspective.”

Steve’s career is a testament to the power of adaptability, discipline, and a people-first approach. His insights remind us that success in investment banking isn’t just about numbers—it’s about relationships, resilience, and relentless growth.