What’s the Most Impactful Leadership Lesson You’ve Learned?

What’s the Most Impactful Leadership Lesson You’ve Learned?

Entrepreneurs often learn powerful leadership lessons on their journey, and we’ve gathered insights from CEOs and Founders to share their wisdom. From the importance of valuing team members to the necessity of remaining flexible and adaptable, discover the eight impactful lessons these leaders have learned.

  • Value Your Team Members
  • Embrace Selective Micromanagement
  • Foster Collaborative Work Cultures
  • Empower and Trust Your Team
  • Commit to Lifelong Learning
  • Lead by Example
  • Distinguish Effort from Success
  • Motivate and Value Your Team
  • Remain Flexible and Adaptable


Value Your Team Members

As an entrepreneur, I’ve learned that the most impactful leadership lesson is valuing individuals within the organization. While the work itself is significant, it’s the people who drive it forward. By showing genuine appreciation and respect for their contributions, I’ve witnessed firsthand how it cultivates a positive and motivated team. 

When people feel valued, they’re empowered to excel and produce exceptional results. So, as a leader, prioritizing the well-being of the individuals within the team is essential for building a thriving business.

Andrew Barry, CEO, Curious Lion


Embrace Selective Micromanagement

Micromanaging is seen as a cardinal sin by many in the management world. However, I’ve learned it can be essential for leadership to be effective. When applied in the right way, micromanagement can speed up learning and development. 

Hand-holding entry-level staff and taking the hand-holding approach, rather than allowing them to figure it out themselves, helps instill a level of judgment. Equally, when dealing with high-detail projects, not micromanaging can allow a tiny detail to turn into a huge problem. As a leader, embrace micromanagement when it’s needed. It’ll certainly pay off in the long run.

Geoffrey Bourne, Co-Founder, Ayrshare


Foster Collaborative Work Cultures

For the longest time, people in leadership have often maintained a hierarchy that bars certain positions within the company from directly communicating with higher-ups unless they go through a very tedious, structured process. 

However, due to the rise of start-up and remote work setups, a more decentralized work culture has started to thrive, allowing for a more transparent, accessible, and amicable discourse between leaders and employees. 

This has certainly fostered a more collaborative and creative environment, allowing employees to have autonomy over their work, as well as the feeling of having ‘a seat at the table’.

Jamie Frew, CEO, Carepatron


Empower and Trust Your Team

The most impactful leadership lesson I’ve learned? Empowering your team. Giving them ownership. Trusting them to make decisions. When you micromanage, you limit your team’s potential. You stifle creativity and innovation.

As a leader, your role is to provide vision and direction. Set clear goals. Then step back and let your team shine. It’s not always easy to relinquish control. But when you do, amazing things happen. Your team feels valued. Motivated. They take pride in their work.

Empowered teams go above and beyond. They find solutions you never thought of. They drive the business forward. If you want to be an effective leader, start by empowering your team. Give them the tools and trust they need to succeed. The results will speak for themselves.

Casey Jones, Founder and Head of Marketing, CJ&CO


Commit to Lifelong Learning

One of the most impactful leadership lessons I’ve learned as an entrepreneur is that the journey of learning never ends.

In the dynamic landscape of entrepreneurship, there are always new challenges to tackle, trends to adapt to, and opportunities to explore. Whether it’s navigating market shifts, refining our business strategies, or fostering a culture of innovation within our team, I’ve come to realize that staying open-minded and continuously seeking knowledge is essential for driving sustained growth and success. 

Embracing a mindset of lifelong learning not only enables me to stay ahead of the curve but also empowers me to lead my company with agility and resilience in an ever-evolving business environment.

As an entrepreneur, I’ve learned that the path to leadership is paved with an insatiable thirst for knowledge and an unwavering commitment to personal and professional growth.

Bradford Glaser, President and CEO, HRDQ


Lead by Example

The most impactful leadership lesson I’ve learned as an entrepreneur is to lead by example. Your team looks up to you as the CEO, so it’s important to show them the work ethic, dedication, and passion that you expect from them. 

By rolling up your sleeves and getting your hands dirty alongside your team, you not only earn their respect but also inspire them to give their best. Remember, actions speak louder than words in the world of leadership.

Alex Stasiak, CEO and Founder, Startup House


Distinguish Effort from Success

The most impactful leadership lesson I’ve learned as an entrepreneur is to always keep in mind when evaluating the performance of your team, effort is not the same as success. The people you are managing may have put in a ton of effort into something but not actually achieved results. 

It’s important to take time to evaluate what they are doing and whether it is working. If it isn’t, it’s time for them to pivot. Not being satisfied with trying hard, but actually ensuring your employees are getting the results needed to grow the organization, is key to being a successful leader.

Tim Johnson, CEO, Health In Tech


Motivate and Value Your Team

One of the biggest leadership lessons I’ve picked up as an entrepreneur is just how key it is to keep your team motivated. It’s not all about just gathering a bunch of skilled people together. It’s really about creating a team that’s not only effective and resourceful but also has that growth mindset. 

I’ve discovered that motivation really starts with making sure everyone feels like they’re valued, that their voices are heard, and that they have the power to step up and make decisions.

Loren Howard, Founder, Prime Plus Mortgages


Remain Flexible and Adaptable

The tech industry is notoriously fast-paced, and rigidity can spell doom for even the most promising startups. A pivotal lesson for me was the importance of remaining flexible and adaptable, not just in our product development but in our leadership approach. 

This mindset enabled us to pivot when necessary, embrace change as an opportunity for growth, and maintain resilience in the face of challenges. It taught me that a successful leader must be willing to constantly learn, unlearn, and relearn to navigate the ever-evolving landscape of the tech industry.

Alari Aho, CEO and Founder, Toggl Inc