The Depth & Breadth of Startup Mentoring

Mentoring is a topic I enjoy discussing and writing about, both of which I’m likely to be doing more in the coming year. The reason is that, in our new venture, my partners and I are taking a serious approach to mentoring that we expect will have a big impact on entrepreneurs.

We recognize that, in the startup world, “mentoring” continues a march towards ubiquity. First-time entrepreneurs are more comfortable asking for guidance, accelerators line up dozens of mentors for portfolio companies, university programs increasingly bring in professionals to help students, and office hours have become a standard in entrepreneurial support.

I find these developments highly gratifying. Not only do I enjoy seeing young or first-time entrepreneurs feel more comfortable seeking cousel, but I also love seeing greater initiative and responsiveness from the mentors. We need to have a lot of this happen if we want to see entrepreneurs succeed.

Of course, there’s plenty of room for improvement. As I’ve written in the past, I still believe we need everyone to be a mentor, especially seasoned business owners and friends of entrepreneurs who don’t get out too often. But another area of opportunity for mentoring is to improve its depth.

Most of today’s mentoring is broad and shallow. In fact, you can argue that most of it really isn’t mentoring at all, but advising. It’s short-term (often one-time) and doesn’t involve much of a relationship. Mentors often simply provide a quick opinion or answer, give advice, and go on their merry way. Most will say, “let me know how I can help”, but it’s rare they’re called upon unless something magical was said during those initial talks.

Real mentoring, on the other hand, is narrow and deep. It involves building trust, building a relationship, and building understanding. It’s a long-term process that requires an investment on behalf of both parties, in both time and energy. It’s more about asking questions, stimulating critical thinking, and continuous learning. Real mentoring doesn’t involve advice or opinions; it involves experiences and discovery.

As I reflected on this comparison, I realized that it was largely a result of my experience “back in the day”. At that time, 10-20 years ago, mentoring was hard work. Mentors were hard to find, proteges put in a lot of effort managing the relationship, and it was a big deal to call someone a mentor.

And that’s what my partners and I expect to accomplish in our new venture. We need all the current advising to continue because it raises awareness, introducing “mentoring” to many more people, and making it more accessible. We believe that what we’re building is simply a necessary next step in the evolution of entrepreneurial mentoring.

We plan to complement the broad-and-shallow variety with the narrow-and-deep kind. We plan to take mentoring to another level, one that’s more permanent and has a greater impact on entrepreneurs and their companies. We plan to take mentoring back to being old-school.


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