What I’ve Learned Running a Mentorship Organization

This guest post is by Carl Shan, the co-founder of CompassPoint Mentorship. CompassPoint Mentorship is a national mentoring venture that pairs up high-school mentees with college mentors for e-mentoring with an emphasis on life guidance.

To learn more about getting involved as a Branch Leader, Mentor or Mentee, visit www.cpmentorship.com

You can get in touch with Carl at carl@cpmentorship.com


“Too often we underestimate the power of a touch, a smile, a kind word, a listening ear, an honest compliment, or the smallest act of caring, all of which have the potential to turn a life around.”

– Dr. Leo Buscaglia

I started CompassPoint three years ago when I was a freshman in college. At the time, I had no intentions for it to expand to anything beyond just a few friends reaching back out to the high-school that we had all graduated from.

Now, three years later, CompassPoint has grown into a national non-profit with Branches throughout California and Maryland. From the original team of just my co-founder and I, CompassPoint has grown to 6 national team members and 15 Branch Leaders. Our team is all composed of students who believe in our mission of delivering free, personalized mentorship from college students to high-school mentees.

During my time helping navigate the direction of CompassPoint, I’ve learned a great deal about leadership, mentorship and myself.

I want to share three key lessons with you today that I’ve learned through my time working with CompassPoint. These lessons apply equally whether you’re a mentor, a leader of an organization or just someone who is curious about growing yourself.

1. Listening Trumps Talking

This piece of insight sounds so obvious, and yet it’s so elusive to integrate into one’s life. Bestselling author Stephen Covey once remarked “Most people do not listen with the intent to understand; they listen with the intent to reply.”

When I started CompassPoint, I initially envisioned that I would be recruiting the most intelligent, knowledgable and mature mentors to dispense their worldly wisdom to high-school mentees.

However, over the course of the time I’ve spent observing and learning from great mentors, I’ve noticed that the most valuable trait they possess is not that they give great advice. Rather it’s their ability to be excellent listeners.

Their mentees are comfortable in conversation with them because they know they are being listened to, and as a result feel able to have honest and open conversations.

I’ve also incorporated this insight into my own leadership by spending more time getting feedback from my team on the direction of CompassPoint than I do spend time trying to dictate my vision of what the organization should be.

2. Check in Frequently

It’s so easy to lose touch with a friend, mentor, mentee or acquaintance. I’ve done it many times, and it is not until later that I see how my lack of communication cost me what otherwise could have been a valuable relationship.

I believe that as a mentor, one of the most powerful things you can do is to check in with your mentee frequently. Many mentees may be comfortable or inexperienced with being the driver of engagement, and it may take just a few words of openness that makes it clear you care.

As a leader of an organization, I’ve also learned how valuable it is to have periodic reflective check-ins. My co-founder and I make time to check in weekly with each other, and then with each of our team members. We ask each other questions like ‘What are you doing well?’ and ‘What do you think you can be improving on?’

Our team members then go on to check in with our Branch Leaders, the students who actually organize a mentorship community at their high school. These Branch Leaders check in with their mentors and their mentors check in with their mentees.

This chain of accountability provides a system of checking in that speaks to the amount of care and attention that is being put in.

3. Be Available and Present…Always

Throughout my life, I’ve found myself in times where I’ve let my work and schedule overshadow my ability to be available to the people around me.

And yet, the most amazing mentors that I’ve encountered have been the ones that, even in the midst of work and pre-planned busyness, nevertheless focus the entirety of their attention on their mentees when they interact.

Bill Clinton’s famous charisma has often been attributed to his legendary ability to focusing his attention on the person he’s speaking with. It’s his trait of making himself available and present to anyone around you that I’ve been drawn to and have attempted to cultivate in my own habits.

At CompassPoint, I’ve made it clear to each of my team members that I want to make myself available for them to talk about anything. They can email, text or call me at any point during my day and I will respond. I want my team to know that I am available and present…always.


I believe that the three points listed above all reflect qualities to be found in the most amazing mentors and leaders. By listening deeply, checking in frequently and making yourself available, you are setting yourself up for the opportunity to shape another person’s life.


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