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The Perilous Struggle: Why Founders Battle to Prioritize Working on the Business Over Working in the Business

How often do you find yourself canceling that vision session with your own team to accommodate a client or to simply cross a task off your list? Is it a one-off or a pattern of behavior? As founders, we’re often entangled in the perpetual challenge of balancing our roles—working on the business versus working in the business. While both are crucial for organizational success, prioritizing one over the other can be a formidable task. Let’s delve into the reasons why we grapple with this dilemma and the potential consequences of failing to strike the right balance.


Immediate Gratification vs. Long-term Vision:

One of the primary reasons we struggle to focus on working on the business is the allure of immediate results. The daily operational tasks offer tangible and often instant outcomes, providing a sense of accomplishment. On the contrary, strategic planning and visionary thinking, essential components of working on the business, require time and patience. The tension between short-term gains and long-term vision can lead founders to prioritize tasks that offer immediate gratification, neglecting the broader perspective that could secure the organization's future.


Micromanagement Tendencies:

Founders who have risen through the ranks or founded a business from the ground up often have a deep understanding of the intricacies of daily operations. However, this intimate knowledge can sometimes transform into a micromanagement mentality. The fear of losing control or the belief that no one else can perform certain tasks as effectively can lead founders to immerse themselves in the day-to-day affairs, leaving little room for strategic thinking and growth-oriented activities.


Lack of Delegation Skills:

Delegating responsibilities is an art that many founders struggle to master. The reluctance to entrust crucial tasks to others may stem from a desire for perfection or a fear of potential mistakes. Unfortunately, this hesitancy to delegate can trap founders in the never-ending cycle of working in the business, hindering their ability to focus on the higher-level aspects that contribute to organizational development.


Failure to Establish Systems and Processes:

Leadership involves more than just putting out fires and addressing immediate challenges. Creating robust systems and processes is paramount for sustainable growth. However, in the rush to handle day-to-day issues, founders may neglect the establishment of efficient frameworks that would eventually streamline operations. The absence of these systems makes it difficult for founders to step back and work on the business, as they remain entangled in the chaos of managing daily tasks.


Shortage of Time Management Skills:

Effective time management is a critical skill for leaders navigating the delicate balance between working on and in the business. The constant barrage of emails, meetings, and urgent matters can easily consume a founder’s day, leaving little time for strategic thinking. Founders who struggle to prioritize and manage their time effectively find themselves caught in the reactive cycle of addressing immediate concerns, neglecting the proactive steps needed for long-term success.


Overplaying Our Strengths and Comforts: 

If given the choice, most of us default to working on the things that play to our natural talents and acquired expertise. However, there's a fine line between gravitating and outright neglecting essential tasks or responsibilities that may not align with your natural inclinations. It becomes problematic if someone constantly avoids or dismisses important conversations simply because they find them less enjoyable or challenging. This behavior could be more indicative of a lack of flexibility, reluctance to step out of one's comfort zone, or a potential blind spot in recognizing the broader needs of the team or organization.


We may never get a day-off from this perilous struggle but by addressing the root causes—whether it be the allure of immediate results, micromanagement tendencies, delegation challenges, lack of systems, time management issues or overplayed strengths and comforts—we can learn to cultivate a balance. It’s a challenge, yes, but also a necessity towards sustained success. We say to all our clients, “be suspicious of your instincts,” especially when you prioritize other organizations and teams over the health of your own.

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