That phrase gets tossed around in leadership conversations all the time. It usually sounds like praise. Meaning someone is adaptable, flexible, and capable of doing a little bit of everything.
Most people forget the rest of the line… master of none.
In theory, broad experience should create stronger leaders. People who understand different parts of the business should make better decisions. But in practice, the results are a little more complicated.
Years ago, while working at Harris Teeter Supermarkets, the structure was simple. People stayed in their lanes. If someone worked in produce, they built a career in produce. The head of that department had decades tied to the produce business. They knew growers. They understood seasonality. They could redesign a process or make a pricing call without needing a dozen approvals.
They could make decisions quickly because they were an expert.
That credibility ran through the entire org-chart. Store managers trusted them. District leaders trusted them. Associates respected them because they started in the same trenches.
The same pattern existed in loss prevention. The people running the program, even before I joined the team, had spent years in the field, investigating cases, walking back rooms, learning the rhythm of retail operations. When they trained a store team or reviewed a case, you knew the advice came from experience. Expertise lived inside the building.
Later, working in a much larger national retailer, the philosophy looked different. Career growth meant movement. Leaders were encouraged to change roles across departments and divisions every 2-3 years. The idea was to build well-rounded leaders who understood the entire organization.
That system produced strong leadership skills. People became good at navigating the corporate complex, managing relationships, developing future leaders, and preparing for the next big role. But it also produced something else.
Generalists.
The produce leader had plenty of leadership experience, cross-functional relationships, and had a clear view of how the organization operated at the highest levels. Did they know when California transitions to Salinas or Yuma for leafy greens? No chance. The same pattern showed up in other departments.
Loss prevention felt it too. Some knew and understood the risks to the business. And some were great at navigating them. They just couldn’t do both. Investigations, security design, and safety response all benefit from leaders who have handled real cases, walked stores after incidents, and seen how problems actually develop. Without that experience, decisions lean more heavily on reports and policies instead of judgment built in the field.
Leadership strength increased, but operational depth thinned out.
The tradeoff matters because expertise catches small problems early. Someone who has spent years in loss prevention learns to recognize the signals before they turn into real damage. They can spot risks to the business that others might overlook and stay steady when a crisis unfolds because they have seen similar situations before. Those instincts come from repetition, not theory.
The difference shows up in shrink results, safety outcomes, and operational consistency.
This is not a criticism of one model over the other. Smaller or regional organizations often grow deep experts because careers stay inside departments for bench strength and succession planning. Large national organizations often build broad leaders because scale demands mobility.
Both approaches bring value. Both carry risk. The opportunity sits in combining them.
Protect subject-matter expertise. Roles in areas like fresh foods, safety, and loss prevention benefit from leaders who have lived in that work.
Create dual career paths. Not every expert needs to become a jack of all trades to advance. Reward mastery in areas such as investigations, safety leadership, or merchandising.
Give leaders broader exposure without abandoning depth. Rotations should expand perspective while allowing people to maintain a core discipline where they remain the undisputed expert.
Retail does not have a leadership problem. It has a balance problem between leadership and expertise. Going with the grain means choosing one model and defending it.
Going against the grain means building leaders without losing experts.
