This is a very painful subject for me. In family businesses with a long history of micro-management, a lack of formal organisational structure, and limited strategic focus, a unique type of leader often emerges: the Loyal Operational Generalist. They are many times some of the most if not the most important key employees of the family business until the family business grows to the stage that it needs to professionalise its governance, strategic focus and organisational structure.

Virtually all family business have a period (sometimes a way too prolonged period) that functions on personal relationships, immediate responses, and the owner-manager’s direct oversight. Chaos, while internally understood, is the default mode. In this reality there are always some leading staff members or managers that become skilled generalists—the “utility players.” They are masters of “doing a little bit of everything” and excel at firefighting and riding the internal waves of chaos. Their value lies in their comprehensive, often intuitive, knowledge of daily operations, allowing them to fill structural gaps and ensure things get done, albeit reactively

As the family business grows and matures, the need to professionalise becomes critical. The business begins to implement governance structures, establishes strategic focus, and formalises its organisational structure. This necessary transition directly challenges the foundation of the Loyal Generalist’s success. In this needed shift, roles become specialised, decisions move from ad-hoc to strategic, and authority follows the structure, not personal history. The business starts rewarding strategic thinking and specialised expertise. The loyal operational generalist suffers most. Their skillset—riding chaos and being operationally reactive—is now a liability. They lack the strategic skills needed for the new structure, struggle to delegate within defined roles, and ultimately are not deemed able to take up a top post they believe they should get based on their past loyalty and commitment to the family business. They often (always) feel their historical value is being erased and may perceive the new structures as unnecessary bureaucracy that slows down “real work” whilst that the family business is being unkind and short changing them for not rewarding them for their commitment over the years.

The loyal generalist’s comfort zone is the old chaos; the business’s imperative is the new order. Their operational depth, once a strength, prevents them from making the necessary strategic step up.

A family business has a responsibility to the loyal individuals who helped it survive the chaotic phase. However, this support must be balanced with the business’s future needs. The family business needs to offer specific training to convert operational knowledge into strategic thinking (e.g., financial planning, market analysis, long-term project management). Pairing them with an external, strategic mentor can be an excellent way to help them step up. Another avenue to explore is that instead of forcing a completely new role to such persons, it would be better to identify a new, strategic role that leverages their deep operational knowledge, such as Head of Operations or a strategic role focusing on key vendor/client relationships where historical knowledge is an asset.

However, there will be cases, where all the efforts will not result in having the Loyal Operational Generalist make the mindset change. This is where separation becomes inevitable, especially when the individual’s resistance actively undermines the professionalisation effort and risks causes significant damage. There are certain bright red signals, like when such Operational Generalists consistently bypass new governance, refuse to follow defined processes, or encourage subordinates to cling to old methods or when fail to transition from “doing everything” to “leading and thinking strategically,” creating bottlenecks and crippling the growth of the business and its ability to create strategies, policies or proper cascading performance measures. In essence when it becomes evident that such Operational Generalist become the principal barrier to the business’s evolution, the hard decision must be made.

The evolution of a family business from an owner-managed enterprise to a professional organisation is an essential, often painful, rite of passage. Family businesses make a fundamental and potentially fatal mistake when they stop the progress on their path to professional governance, internal structures, and strategic focus simply to appease individuals who cannot or will not adapt. Ultimately, whilst a business must nurture and care for all team members, the business remains to be greater than any single individual. Protecting a few legacy positions at the cost of crippling future growth means condemning the entire business—and all its stakeholders, including the next generation—to stagnation or failure.

In conclusion, leadership must be courageous. While compassion dictates offering a path for transition, the business’s mandate requires prioritising the professional structure that ensures long-term viability and success. It’s a transition that trades the comfort of the familiar past for the necessity of a prosperous future.