Lesson Learned: Make sure to spend time and energy evolving and growing yourself as your organization grows

Alan Gilbert
2 min readJul 18, 2023

This blog post is the last of a series of leadership lessons that I have learned from 40 years in tech. I hope that people have enjoyed reading them as much as I enjoyed writing them. They have helped me understand everything I have learned over the years, and have “scratched my itch” to give back to the community.

The best founders, particularly those who are first-time entrepreneurs, devote considerable time and energy to ensure that their growth as leaders parallels that of their businesses. They understand that the areas they once prioritized while leading a small team of five no longer hold the same significance when overseeing a company of 50 or 200 individuals. Consequently, they redirect their focus towards high-leverage and impactful activities, such as growth strategy, fundraising, and enterprise sales.

They foster personal growth through continuous self-development, seeking guidance through coaching, and a relentless drive to learn and improve. Furthermore, they cultivate leadership qualities in others and delegate tasks and decision-making to enable them to focus on the company’s most important areas and decisions. They dedicate their time to strategic matters, while effectively delegating more tactical responsibilities to skilled operators. This cascades further as leaders foster the development of other leaders, relinquishing less critical decisions to their capable hands.

This approach has two additional advantages. Firstly, it allows organizations to stay nimble as they grow, enabling timely decision-making in critical moments. Secondly, it ensures better tactical decisions as they are made by people with the deepest understanding of the subject matter. To allow all of this to happen, company leaders have to do a great job of communicating the company’s strategy, mission, and vision, enabling each decision-maker to act as their proxy.