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Mentoring is at the Heart of Entrepreneurship


Latest posts by Jason Scott Montoya (see all)

Teaching and mentoring is at the heart of entrepreneurship. As business owners, we’re teaching our prospects how our company can help solve their problem. With our team, we’re teaching and communicating our vision and how we’re to take care of our customers. With our company leadership, we’re teaching how to guide their respective functions of the business. The capacity of our company is based on our team’s collective capacity to lead. The best way to increase this capacity is to teach our leaders.

So how do we best go about this?

Let’s start by understanding the four levels of teaching, how it applies to business and then a framework for how we can take action.

The four stages of teaching

The first of the four stages is when we are the student. We are taught by the teacher. We listen, and we ask questions. Once we’ve gained an understanding, we become a practitioner. We practice what we’ve learned and realize the nuance of what we’ve been taught. Real world challenges force us to adapt our perspective and a deeper understanding of the underlying principles emerge. We’ll eventually gain experience, leading to a deeper wisdom as to how it all fits together.

Our third stage is teaching students and practitioners. This is our opportunity to fill the gaps of what we know, and more importantly, to understand how we know what we know. Our students reflect our strengths and weaknesses and they act as a real-time mirror. Practitioners challenge us with how the principles and fundamentals actually help them in the real-world.

The fourth and final stage in mastering our craft is teaching teachers. It’s the step that ensures the insights we leave behind will live on beyond us. It becomes a legacy for generations to follow. In this stage of teaching, we are two steps removed from the student and our diluted level of control illuminates additional challenges and growth opportunities as we learn the final gaps in our own understanding of what we teach. This is both the most challenging and rewarding stage to operate within.



The stages applied to our business

In many ways, these stages reflect the progress of a small business. When I first wanted to launch my company, I acted like I knew what I was doing, but deep inside I was scared and unsure of how to make it happen. I was the student and I tapped into teachers around me, both good and terrible ones. I learned from these teachers, but I was always delaying the actual jump into full-time entrepreneurship.

It wasn’t until I got a push from my wife to either launch the business or get a job that I made the leap from student entrepreneur to a practitioner. I quickly realized the limitations of my head knowledge as real business challenges came at me from multiple directions. How do I find new clients? How do deliver on the work I’ve sold? How do I hire people to support me? How do I manage all of these dynamics all at once? Chaos descended upon me, and the business and the stress and anxiety soon followed.

My lack of maturity as a business owner hindered my ability to effectively address these questions and I struggled through the process. But, I learned and I grew as I cultivated a team around me. As I got a handle (after many years) on what I was doing and was able to make progress, I shifted into teaching my leadership team. How could I empower them to lead the company without my constant hands-on involvement? This is when I taught what I knew to my team while simultaneously tapping into resources and programs for effectively handling their respective functions of the company.

As they got a healthy handle on their respective role in the business, the challenge shifted to them teaching those that followed their lead within their respective functions of the business. This also changed how my leadership team needed me. How could I teach my leadership team to teach and guide those within their area of responsibility? As a small business owner, it’s much easier to go past my leadership team and deal directly with those people to make things happen, but doing so can be short-sighted. These downsides can make it challenging to build a scalable business. The key is to embrace these challenges and changes to grow our companies. If we do, we can set a plan for anticipating and moving to and through these stages.

I’ve established four checkpoints below to help us navigate this path.

Take action on mentoring others

Flourishing as a small business owner requires we share what we’ve mastered. Sharing what we master is about teaching what we know and sharing stories of failure and success. In our journey toward success, we’ll pass four mile markers that let us know we’re moving in the right direction. These four checkpoints will help us take actionable steps through the four stages of teaching in our life and business.

The first checkpoint is when we are seeking others out to share our insights and stories. Others share of their current business challenges and we feel an immediate connection. Impulsively, we share how we overcame in similar situations. After sharing with multiple people, we’ll realize how much our insight helps, but we’ll also face the challenge of our own limitations. We only have so much time to share one-on-one what we know.

Out of this limitation, we’ll pass our second mile marker where we decide to broadcast what we know. Through short form writing or public speaking, we’ll begin communicating our insights publicly with others so more people can benefit than those we have time to meet with individually.

As we continue to share with others in this capacity, we’ll realize the limitation of our broadcasted insights. While it will help many, it fails to address the intricacies of each individual’s circumstances. It’s at this point where we’ll need to dive deep into the lives of others in ongoing mentorship. At the same time, we still have the limitation of time, so we’ll leverage group mentoring so we can go deep and wide. This place of actively mentoring others is our third milestone in our journey to share what we’ve mastered.



As we progress down this road of teaching, we’ll soon realize that we won’t always be available or even alive to help others. So, how do we help people beyond our capacity or lifetime? How do we leave a legacy that will impact generations to come? It’s at this point where we seriously explore a permanent beyond-us system that can help many more when we’re unable, unwilling or not around. Here we write a book, create video courses, record audio podcasts and tap into multiple mediums to capture what we know in a way others can tap into when it’s more appropriate and relevant to them.

With a mindset of creating a beyond-me system, we capture the mindset of creating a scalable and profitable business model. The scary challenge is recognizing the lifetime of our involvement in the business and being ready and willing to let our company go. It’s not until we learn to actively release that we’ll consistently experience growth. Proactively letting go allows us to embrace the journey of progress.

Originally published May 2, 2017.



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