• --j

3 Reasons most mentorships fail & How to avoid them

Successful mentorships are as rare as hen's teeth in this digital age of instant gratification. It's unfortunate, but it's true.

It is still possible to have a healthy or even thriving mentorship. Still, there are also reasons that mentorships are doomed to fail before they begin. I want to address three of the most common causes in this post.


One of the most obvious reasons that a mentorship fails is fear. More specifically, fear on the part of the mentor. Being chosen as a mentor does not automatically cure self-doubt or a general lack of confidence. When a mentor realizes the weight of their mentoring responsibilities, it can be overwhelming. Mentors often begin to question themselves. They begin to say, "What if my apprentice figures out that I don't have it all together?" or "I'm afraid I will give poor counsel or lead them down the wrong path, then it will be all my fault."

How to combat it:

Start off strong by being weak. I know that sounds counterintuitive, but vulnerability is the cornerstone of mentorship. Tell your apprentice that you will do the best that you can to pass on the things that you have learned along the way, but you reserve to right to be wrong from time to time. Tell them that you are not perfect, feel free to share with them some of your weak areas or areas that you are working on. If possible, tell them about your mentor and let them know that when you don't know what to do, you will reach out to them for counsel.

Lack of material

Mentorship is a long term commitment. When that begins to sink in, you realize that you will need a lot of material to maintain a growing apprenticeship. Some mentors run out of things to pass on within a matter of weeks or months.

This is why people who have not been adequately mentored, struggle with mentoring others. They are trying to pass on information that they have learned themselves. Conversely, someone who has been well mentored is (ideally) passing on generations of material that has been acquired through varied people, lifestyles, and experiences.

How to combat it:

This is the very reason I always say you need a Timothy AND a Paul in your life. If you have a mentor yourself, you are being poured into regularly. That means that you have a steady flow of wisdom and insight to pass on to your apprentice.

So, if you are struggling with a lack of material, find some new mentors in your own life. As you learn from them, put things into practice and pass them on to your apprentice.


Mentorship requires an uncomfortable level of transparency. For us to grow, we must be brutally honest with ourselves and those that we lead. Mentors and apprentices need to give an all-access pass into each other's lives. There certainly must be boundaries, but you need to be able to discuss things that are very personal and even sometimes humbling.

A mentor must be able to confess his own missteps for his apprentice to learn from them. An Apprentice must trust his mentor enough that he can share his most profound struggles. If there is no transparency, the communication will be vague and murky.

How to combat it:

Don't have stale "Apprenticeship meetings" in neutral locations like coffee shops or offices. Instead, meet in places where you are living and working, it is there that you will find authenticity. Spend time around each other's friends and families. It will help you to see things from a different perspective.

Ask the right questions. I give some great lists of questions for mentors and apprentices in my book "Letters to an Apprentice."

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