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From Entrepreneur to Organizational Leader: Leading Through Critical Transitions

Many leaders are faced with the challenge of taking their organizations to another level.


This transition comes in many forms, such as an entrepreneur who has successfully taken the company to a point that will require a team of leaders to continue the progress; a family business that has been around for years that must hand it off to the next generation; or a company that exists successfully in its market and sees opportunity in a larger or expanded market.



This is where organizations often hit a wall. The problem, as with individual career development, is the behaviors that created success at one level all but guarantee failure at the next.


For example, as entrepreneurs drive their business to success, they should turn a blind eye and deaf ear to all those who say it cannot be done. They must be aware of all the obstacles facing the fledgling organization and overcome them, often through sheer determination.


As the organizations grow, however, their capacity is reached and they become the bottleneck. The tactics that bring an organization to life become the behaviors that stunt their growth.


Responsibility Turnover


Entrepreneurs must transition from the hero leading the charge and creating a successful start-up through sheer will and determination to steward leaders whose influence strengthens a management team and creates scalable alignment with the mission.



It is critical to identify this behavioral change as an emotional process more than a cognitive one. People don’t do what they do because of what they know, they do it because of how they feel. How many times do parents ask their children, “Why did you do that – you know better?” That’s the wrong question. Seeking to understand feelings would be more fruitful.


Likewise, it is no wonder entrepreneurs, who have invested their energy and identity to bringing organizations to life, have trouble turning the company over to someone else. Contrasting perspectives are seen emotionally as the enemy to progress and a personal affront. An entrepreneur struggles to distinguish the feedback of pessimistic naysayers from those who could be trusted advisors. The habit of going full speed ahead without considering the risks that were required in the organization’s infancy ceases to be a necessary survival technique and becomes destructive.


When this happens, the introspection required to improve leadership and results lies outside the realm of consideration. The leader is often seen as ego-centric, with self-awareness viewed as the missing characteristic. Therefore, entrepreneurs are not aware of their full effect on their organizations.


Research and experience show the twin characteristics of great leadership to be humility and strength of will. In a culture where humility is interpreted as weakness, it is a characteristic that proves to be a prerequisite for influential yet invisible leadership. Humility alerts entrepreneurs to habits that restrict empowerment of the next generation of leaders and helps overcome them.


Overcoming Personality


Because this transition is so difficult, many think it’s impossible. The very term entrepreneur creates an insurmountable obstacle. It’s often believed by labeling a personality type, one can categorize and predict behavior. If you want to avoid change and excuse your behavior, identify your personality type and say, “That’s just the way I am.”


To overcome the behavioral obstacles to leading at the next level, you have to identify what you really want and do what it takes to get there. The key to change won’t be found in the deterministic thinking of personality typing. You can begin the journey by identifying a compelling value proposition.


The process of leading through critical transitions lies in three overarching components:


First, identify a compelling vision for your future role. This will be something worth working for. It will bring personal fulfillment and be aligned with the ongoing needs of the organization.

Second, create an organizational structure starting with the leadership team you trust. This does not mean cloning yourself. This would only serve to increase overhead without embracing the diversity of thought or skill required for the larger organization.

The third and most difficult step is to change habits. This is where the combination of humility and strength will be required in large doses.

With a compelling vision, the right team of leaders, a solid game plan and good coaching, the entrepreneur can learn to become a leader of greater influence while unlocking the potential of the organization.

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