Employing or promoting individuals with a strong operator’s mindset into managerial positions is a common pitfall for many family businesses. While the dedication and efficiency of operators are invaluable at a certain level, an over-reliance on this skillset in leadership can stifle growth, innovation, and long-term sustainability. This article explores the issues arising from such appointments, drawing insights from Simon Sinek’s “Infinite Game,” Stephen Covey’s “The 7 Habits of Highly Effective People,” and Daniel Kahneman’s “Thinking, Fast and Slow,” and outlines strategies for fostering a balanced, strategic approach to management within family enterprises.

An operator, by nature, is focused on the immediate, the tangible.They excel at problem-solving in the here and now. These are crucial qualities for any business, especially in the day-to-day running of operations. However, when an individual with an exclusively operational mindset assumes a managerial role, several issues will arise:

• Short-Term Vision over Long-Term Strategy (Sinek’s Finite vs. Infinite Game): Simon Sinek, in “The Infinite Game,” argues that many businesses operate with a “finite mindset,” focusing on quarterly results, market share, and beating competitors. Operators are inherently wired for this finite game – achieving specific, measurable outcomes within a defined timeframe. A manager, however, needs an “infinite mindset” – one that focuses on enduring purpose, resilience, and continuous improvement, understanding that the game of business has no end. An operator-turned-manager often struggles to shift from winning the day’s battle to envisioning and building for the future. They might prioritise immediate cost-cutting over strategic investments in R&D or employee development, unknowingly compromising the company’s long-term health.
• Focus on the Urgent over the Important (Covey’s Eisenhower Matrix): Stephen Covey, in “The 7 Habits of Highly Effective People,” highlights the Eisenhower Matrix, which categorises tasks into four quadrants:
  • Urgent & Important: Crises, pressing problems.
  • Not Urgent & Important: Prevention, relationship building, planning, new opportunities.
  • Urgent & Not Important: Interruptions, some meetings, popular activities.
  • Not Urgent & Not Important: Trivia, busywork.
    Operators naturally gravitate towards Quadrant 1 (Urgent & Important) and Quadrant 3 (Urgent & Not Important) tasks because these demand immediate attention and provide instant gratification through resolution. A manager with a strong operator’s mindset will spend most of their time firefighting, reacting to crises, and getting bogged down in day-to-day urgencies. They struggle to carve out time for Quadrant 2 (Not Urgent & Important) activities – strategic planning, developing their team, and identifying future trends – which are crucial for long-term growth and preventing future crises.
• Decision-Making Biases (Kahneman’s Thinking, Fast and Slow): Daniel Kahneman’s “Thinking, Fast and Slow” introduces System 1 (fast, intuitive) and System 2 (slow, deliberate) thinking. Operators often rely heavily on System 1 thinking, making quick decisions based on experience and intuition to solve immediate problems. While efficient for routine tasks, this can lead to cognitive biases when applied to complex managerial decisions. They might jump to conclusions, fail to consider all variables, or be overly influenced by recent events (availability heuristic), rather than engaging in the slower, more analytical System 2 thinking required for strategic planning, risk assessment, and complex problem-solving. This can result in reactive, rather than proactive, management.
• Micro-Management and Resistance to Delegation: An operator’s ingrained habit of “doing” can manifest as micro-management in a managerial role. They might struggle to delegate effectively, believing they can perform tasks better or faster themselves. This not only burdens them but also stunts the growth and development of their team members, creating a bottleneck and disempowering employees.
• Inability to Adapt and Innovate: The operator’s focus on established processes can lead to rigidity and resistance to change. When market conditions shift or new technologies emerge, an operator-minded manager may struggle to adapt, prioritizing the comfort of familiar operations over the necessity of innovation. This can leave the family business vulnerable to more agile competitors.
• Creating Indispensable Dependency and Operational Fragility: Because an operator-minded manager is so deeply involved in the day-to-day execution and problem-solving, their teams often become overly reliant on their direct input and decision-making. This lack of empowerment and independent problem-solving skills among team members means that when such a manager eventually leaves the company, they leave behind significant operational difficulties. A whole mess with a big black hole. The team, accustomed to being directed and having issues solved for them, is ill-equipped to operate effectively without their constant presence. This directly contradicts Covey’s principle of interdependence (Habit 4: Think Win/Win; Habit 5: Seek First to Understand, Then to Be Understood; Habit 6: Synergise), where effective teams are built on mutual reliance and shared competence, not on the singular brilliance of one individual.
• Neglect of Scalable Control Systems and Processes: A strategic manager understands the importance of building robust, self-sustaining systems and processes that allow the business to operate efficiently without constant direct intervention. An operator, however, often focuses on immediate problem fixes rather than system-level solutions. They may not prioritize establishing clear protocols, documentation, and automated controls, because their “System 1” (Kahneman) preference for quick action leads them to solve problems as they arise, rather than investing the “System 2” effort into designing systems that prevent problems or allow others to solve them autonomously. This creates a reliance on individual heroics rather than institutional strength, leading to inefficiencies and vulnerabilities in the long run, and hindering the company’s ability to scale operations sustainably, a key tenet of an “infinite mindset” (Sinek).

The Importance of a Balanced Managerial Mindset

For family businesses to thrive, managers need to balance operational excellence with strategic foresight. This means cultivating individuals who can:

See the Big Picture: Understand how daily operations contribute to the overarching vision and mission of the company.

Think Long-Term: Plan for future growth, market shifts, and succession, rather than just the next quarter.

Prioritise Strategically: Allocate resources and time to important but not necessarily urgent activities.

Empower and Develop Teams: Delegate effectively, mentor employees, and build a culture of shared responsibility.

Embrace Change and Innovation: Continuously seek new opportunities, adapt to challenges, and foster a culture of learning

How to develop Balanced Managers

Balanced Managers do not grow on trees. So the following is needed to increase the chance of developing balanced managers:

Provide Strategic Training and Development: Don’t assume that a good operator will naturally become a good manager. Invest in training that focuses on strategic planning, financial literacy beyond basic budgeting, leadership skills, change management, and even courses on cognitive biases and decision-making. Consider external programs or bringing in consultants.

Mentorship and Exposure: Pair aspiring managers with experienced leaders who embody a strategic mindset. Expose them to board meetings, high-level discussions, and cross-functional projects that require a broader perspective.

Define Managerial Roles Clearly: Explicitly outline the strategic responsibilities of managerial positions during the hiring or promotion process. Ensure candidates understand that the role extends beyond day-to-day operations.

Implement Performance Metrics Beyond Operational KPIs: While operational metrics are important, introduce KPIs that measure strategic contributions, such as successful project implementations, team development, innovation initiatives, and long-term financial health.

Identifying a Lack of Strategic Mindset in Candidates

When employing or promoting individuals to managerial roles, look for these red flags indicating a potential lack of strategic thinking:

Hyper-Focus on Technical Details: During interviews, if a candidate consistently dives into granular operational details without demonstrating an understanding of the broader context or impact, it could be a warning sign.

“How-to” over “Why”: They might excel at explaining how something is done, but struggle to articulate why it’s done or what its long-term purpose is.

Lack of Vision and Future Planning: When asked about future challenges or opportunities for the business, their responses are vague, reactive, or limited to immediate operational adjustments.

Difficulty with Hypothetical Scenarios: Strategic thinking requires envisioning different possibilities. If they struggle with “what if” questions or scenarios that require abstract thought, it’s a concern.

Limited Interest in Industry Trends or External Factors: A strategic manager stays abreast of market changes, competitor actions, and technological advancements. A purely operational mindset might show little interest beyond the immediate confines of their department.

Inability to Delegate or Empower: Look for signs of micro-management in past roles or a reluctance to discuss how they would empower a team.

Resistance to Change: If they express skepticism or discomfort with past or hypothetical changes, they might lack the adaptability required for strategic leadership.

In conclusion, when family businesses,
consciously seek to identify and cultivate a balanced blend of operational and strategic thinking in their managers, they can overcome the “operator’s trap” and build resilient, innovative, and enduring enterprises ready for the infinite game ahead. They would avoid being traumatised everytime a manager choses to leave the enterprise discovering a mess he or she has left behind – an organised mess he or she could only operate with, using his or her operator’s mindset.