Podcast Summary: Building Learning That Fits the Pace of Fast-Moving Operations with Gregg Summers of Sysco
When you listen to Gregg Summers talk about learning and development, one theme surfaces again and again: learning works best when it is grounded in real work, real people, and real conversations. As Field Director of Learning and Development at Sysco, Gregg operates at the intersection of frontline performance, leadership development, and business impact. His perspective is shaped by decades inside a global organization and by a deep belief that the most powerful learning moments often start with curiosity, not content.
In this episode of Learning Leader Spotlight, Gregg joins Leigh Anne Lankford, President of TrainingPros, for a thoughtful conversation about the evolution of L&D, the role of mentorship, and why asking better questions may be the most important skill learning leaders can build today.
From Sales to Learning: A Natural Transition
Gregg’s path into learning and development will feel familiar to many L&D professionals. He did not start his career with the intention of becoming a learning leader. Instead, he spent years on the sales and sales leadership side of the business, where his curiosity and ability to break down complex ideas stood out.
That skill eventually led colleagues to ask him to step in and teach portions of training programs. One session turned into another, and before long, Gregg realized he had found work that energized him. Teaching adults, facilitating conversations, and helping people see situations from new perspectives felt natural.
Like many who “fall into” L&D, Gregg discovered that learning was not just something he did well. It was part of who he was. That realization shaped the next phase of his career.
Learning Where the Work Happens
Today, Gregg leads learning efforts that directly support Sysco’s field operations. His team works closely with warehouse teams, delivery drivers, and frontline leaders, designing learning in the flow of work where sitting at a desk for an hour-long course is not realistic.
This context has deeply influenced how Gregg thinks about learning design. He understands that relevance and respect for time are non-negotiable. Learning must earn attention by solving real problems, not by checking boxes.
That same mindset extends to his leadership development work, which reaches all the way up to the vice president level across the organization. Whether working with frontline teams or senior leaders, Gregg’s focus remains the same: learning should help people perform better in the moments that matter most. Performance improvement is key.
How Learning Changed After 2020
When asked about the most impactful changes in learning and development over the past few years, Gregg points to the shift that came with 2020. Suddenly, geography mattered far less than it ever had before.
Virtual delivery made it possible to connect people across regions, countries, and functions in ways that were previously impractical. Gregg now facilitates learning experiences with participants from across North America and beyond, sometimes bringing in subject matter experts who would never have been available for an in-person session.
This expanded reach also changed how organizations think about collaboration. Learning is no longer limited by travel budgets or room capacity. The question has become not “Who can we get in the room?” but “Who should be part of this conversation?”
At the same time, Gregg is clear that in-person learning still matters. As organizations return to more face-to-face experiences (ILT), the challenge is finding the right balance between reach, cost, and human connection.
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Designing Learning That Fits Real Life
One of the most practical insights Gregg shares is about how people actually learn during their day. He describes starting his mornings by listening to podcasts while walking, absorbing information in a way that fits naturally into his routine.
That habit has shaped how he thinks about learning delivery. Instead of defaulting to long, formal courses, Gregg encourages learning leaders to think in terms of options. Short-form content, micro learning, longer deep dives, audio, video, and live discussion all have a place depending on the audience and the moment of need.
This approach is especially important in operational environments where time away from work has real consequences. Asking someone to step away for a full hour only makes sense if the learning experience truly delivers value.
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Proving the Value of Learning on the Frontline
When Gregg’s team first began partnering more closely with the supply chain side of the business, learning and development was not always seen as essential. Many employees were not used to structured learning offerings, and skepticism was common.
Rather than pushing programs, Gregg’s team focused on building relationships and demonstrating value. Over time, trust grew as leaders and frontline employees saw that learning was designed to support their work, not interrupt it.
This experience reinforced a lesson many learning leaders know well: credibility is built through relevance. When learning solves real problems, people lean in.
The Power of Mentorship
Mentorship is a central theme throughout the conversation. Gregg credits much of his own growth to strong mentors, including the leader of Sysco’s global learning organization, who modeled curiosity, adaptability, and a willingness to challenge the status quo.
He also speaks passionately about being a mentor himself. Gregg has volunteered as a mentor, sometimes maintaining those relationships for over a year. These long-term connections create space for honest conversations and perspectives that are difficult to see when you are deep inside your own role.
For those aspiring to leadership roles, Gregg believes mentorship is invaluable. It requires vulnerability, the willingness to ask for help, and the humility to listen. Yet most people, he notes, are flattered to be asked and happy to say yes.
The Skill That Matters Most: Asking Better Questions
When asked to name the most important skill in the workplace today, Gregg does not hesitate. For him, it comes down to asking good questions and truly listening.
Too often, professionals feel pressure to jump straight to solutions. Gregg argues that slowing down, asking one more question, and listening a little longer often reveals the real issue beneath the surface.
This skill shows up everywhere, from sales to leadership to learning design. Gregg shares how asking questions helped him succeed in sales by making customers feel heard and valued, not sold to. That same principle now guides how he coaches leaders and designs learning experiences.
In a world full of quick answers, curiosity remains a differentiator.
Staying Connected to the Business
Gregg also emphasizes the importance of staying current with industry trends. He regularly reads curated industry news, global business insights, and publications specific to the markets Sysco serves.
This habit helps him connect learning initiatives to real business conditions. When learning leaders understand the pressures their stakeholders face, they can design experiences that resonate and feel timely.
A Book Recommendation for Learning Leaders
For those looking to grow into learning leadership roles, Gregg recommends The Coaching Habit by Michael Bungay Stanier. The book focuses on building curiosity through better questions and encourages leaders to resist the urge to immediately provide answers.
Gregg appreciates its broad applicability. Whether designing training, coaching a team member, or leading a department, the habit of asking thoughtful questions can transform how leaders show up.
Final Thoughts
Gregg Summers embodies a grounded, human-centered approach to learning and development. His insights remind us that effective learning is not about doing more. It is about doing what matters.
By focusing on mentorship, curiosity, relevance, and listening, Gregg offers a vision of L&D that strengthens both people and performance. For learning leaders navigating constant change, his message is clear: slow down, ask better questions, and let learning grow from there.
Listen to the full interview here.
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