Compass Staff |
What will it take to lead in a retail landscape transformed by AI and rising expectations from employees and customers alike?
That was the question behind Guild’s Retail Meeting of the Minds, held in conjunction with the organization’s Opportunity Summit 2025 in San Diego, where a cross-section of seasoned retail leaders gathered to discuss how the role of the store manager will evolve over the next five years.
In contrast to the doom-and-gloom narratives that often dominate retail-industry headlines, the group of 15 senior leaders surfaced something somewhat unexpected: actual optimism, albeit cautious, that technology may actually strengthen retail’s human leadership — rather than diminish it.
Across the four-hour session, the 15 participants explored topics ranging from the paradoxical role AI will play in frontline environments to the rising importance of trust and loyalty to the shifting motivations of next-generation workers. They also identified the human capabilities retail managers will need most in the decade ahead: skills like emotional intelligence, curiosity, discernment, culture shaping, persuasion, mentoring and coaching, resilience, learning agility, change leadership, and creativity — especially those that help managers coach employees toward their “why” rather than simply directing tasks.
Here are three insights that stood out to us.
1. Retail managers must be both ‘operator’ and ‘ecosystem leader’.
Success in retail has long been defined through the speed, accuracy, and consistency of transactions. But the retail manager’s remit is increasingly expanding beyond “transactional operator” to become “ecosystem leader,” a new role that requires them to create and maintain loyalty and purpose across their employees, customers, and the community at large.
This expanded remit shows up in two distinct but connected ways.
On one hand, for many retailers, OSAT (Overall Satisfaction) — an aggregate of Google, Yelp, Apple Maps, and in-store surveys — is now strongly tied to store-level profitability. When OSAT rises, free cash flow follows. OSAT is now almost one for one with the skill and mindset of the general manager.
On the other hand, managers are increasingly expected to be “culture-shapers”. This can be attributed in part to younger employees wanting more purpose in their daily work, which also has become a small but powerful lever for engagement. “Purpose is in the tasks people choose every day,” one leader pointed out.
On this point, participants also noted that helping team members connect their daily responsibilities to a deeper sense of purpose — their “why” — is becoming a core managerial skill. Another is to stop “putting out fires” themselves. In other words, instead of absorbing every escalation or challenge, effective managers must empower and coach their teams to solve problems, building capability rather than bottlenecks.
One conclusion from these insights: Tomorrow’s retail managers may need an entirely new skill set — one capable of running the store while also shaping the loyalty ecosystem across employees, customers, and the community.
Many Guild retail learners achieve mobility before completing their program, a sign that skill-building is creating measurable value in real time on the floor.
2. AI will remove transactional burdens but raise the bar for human leadership.
Despite the intensifying debate about automation’s impact on frontline jobs, leaders told us that AI is actually amplifying managers instead of replacing them.
“Take all their sh*t work and give it to the robot,” as one participant put it, to nods around the room.
We know that AI can relieve managers of scheduling, inventory workflows, reporting, approvals, and other repetitive tasks that currently dominate their day. And that many managers spend their shifts navigating legacy systems and transactional processes that distract from important work like developing people, solving problems, and creating a sense of purpose for their teams — the very work managers often struggle to prioritize because they’re dealing with immediate crises.
Yet therein lies the paradox. As AI strips away transactional tasks, the human responsibilities of the role become more important. Managers will need sharper emotional intelligence, clearer communication, deeper coaching capabilities, and the ability to build trust with workers navigating uncertainty, everyone in the room agreed. They will also need to guide employees through change, helping frontline teams understand why AI is being deployed, how it helps them, and how it creates new opportunities rather than replacing them.
Guild’s frontline leadership data bears this out. In Guild’s “Leading Your Location” curriculum — designed specifically for retail and location-based managers — learners build capabilities in communication, de-escalation, coaching, diagnosing performance, and adopting AI tools effectively. The curriculum focuses on helping managers “think like general managers,” interpret financial metrics, and lead through rapid change. Importantly, the program also supports new managers during the notoriously challenging transition from individual contributor to leader — a moment when many are promoted on potential and then left to sink or swim, often leading to burnout without targeted support.
In this context, AI marks shift toward a more human — and more complex — form of leadership.
3. The next generation of retail managers will need a different skill set — and a stronger value proposition.
Interestingly, the skills our group of experts identified as the most critical for the decade ahead were neither operational nor technical. They were overwhelmingly human: skills like emotional intelligence, coaching, discernment, resilience, persuasion, learning agility, creativity, and culture shaping — the skills new managers struggle to apply “in the wild” without adequate coaching and support.
But there’s a caveat, they said. While these human capabilities matter deeply, what drives urgency inside retail organizations are measurable business outcomes tied to operational and financial performance. As one retail leader explained, executives care about OSAT, throughput, and free cash flow — and they want learning solutions that move those metrics directly.
This raises an important question: How do you design leadership development that builds human capability and drives operational performance?
Guild’s learner data offers helpful insights. Retail learners in People Management & Leadership programs in Guild’s Learning Marketplace have experienced a 4x salary uplift compared with colleagues who do not participate in learning.
At the same time, we also see strong demand patterns that reveal what frontline workers need most to advance: Over the past 12 months, business administration degrees (AS and BSBA) were among the top-enrolled programs for retail learners.
Critically, 76% of Guild's retail graduates remain with their employer 12 months after completion. In other words, when frontline workers see a path forward — supported by strong coaching, clear advancement pathways, and the right mix of skill development — they stay longer, perform better, and move into roles that strengthen store operations. Guild data also shows that many learners achieve mobility before completing their program, indicating that skill-building is creating measurable value in real time on the floor.
The leaders in the room corroborated this, telling us that fewer frontline workers are raising their hands for leadership roles because the jobs feel overwhelming, under-supported, and insufficiently compensated for the responsibility required. Several emphasized the need to redesign the manager value proposition by connecting AI-enabled efficiencies to real advancement opportunities, certifications, and continued learning — much like the structured journey outlined in Guild Academy’s frontline leadership model. They also noted that organizations must intervene earlier — especially when new managers are first promoted — with coaching, mentorship, and resources that help them build confidence rather than burn out.
Where this leads
Retail leaders at the Meeting of the Minds envision a retail manager equipped to:
Build loyalty across employees, customers, and communities;
Leverage AI to remove friction and focus on meaningful human interactions;
Cultivate purpose and autonomy on their teams;
Balance human capability with operational and financial acumen; and
Lead through ambiguity with empathy, curiosity, and resilience.
This may sound like an optimistic vision, but it’s an actionable one. For retailers facing tightening margins, rising expectations, and a new generation of workers motivated by purpose over promotion, these insights point to a possible future where retail’s most human work becomes its most strategic advantage.
