On Mentoring and Trust / When Someone looks up to you

On Mentoring and Trust / When Someone looks up to you

I recently read “On Raising Boys” and it brought out some very interesting points that I think apply to start-ups as well. One of the three key phases to development for a boy is having mentors in his teen years that are outside their main family unit, that have perspective, and come with authority in some field.  He can rely on this guidance to make important decisions outside of his direct family unit while building interdependence and confidence on his own.

Same goes for mentoring entrepreneurs.

I recently wrote about my mantra of Discover. Develop. Deliver. Which in very broad terms means I am always looking for young-at-heart entrepreneurs with fresh ideas. But equally important is the willingness to develop themselves  their product, the message, etc.

So here are some experiences I have drawn from mentoring lots of entrepreneurs over the years:

Know what you are mentoring to

Sounds crazy, but often the mentee does not know what they want out of the relationship. “Sounding board” is often the catchword for “ I need someone to talk to”. Rather than that generalization, I find I have always been more effective when we focus on a specialty need. It could be finances, business models, business development, partners, motivation, time management, you name it. But knowing what the mentee wants out of the relationship allows me to think on their behaf through the lens that they asked for guidance.

I don’t give personal advice when business advice is asked for- or vice versa.

I try to share my experience wherever possible. I tried this… I realized this…. I once had trouble with this… so that the entrepreneur can see things through another lens, and not be defensive about hearing “you should do this.. try this… break that. Entrepreneurs are tense enough; they don’t need an office parent telling them to eat their vegetables. I was reminded recently of one of my classics in this category: breakfast begins at 8. I work with so many younger entrepreneurs, who has a quite different idea of “bedtime” on “school-nights”. Rather than try to correct that behavior, I simply scheduled important meetings at 8am. They soon got the message that no matter what is done the night before, the bill is due in the morning. Here’s the link from Richard Dinan ‏ breakfast is at 8 🙂

And I try to help people discover the talents within themselves by asking questions. Lots of questions. Lots and lots of questions. Eventually, we run the table from vision to execution and are ready to make some bold decisions. Having what Covey called “the courage of our convictions” means all the available facts have been surfaced, and intelligent discussion held, and the best course chosen. It’s never a lock, but it sure helps to enter the rapids with some sort of thought out plan.

And, most importantly, I try to behave like someone whose opinion is often sought. That’s perhaps the most important lesson of all.

Work with a mentee that actually is coachable

Some mentees want window dressing: so-and-so is on my Advisory Board. Some want a sounding board, but have their minds made up anyways. Some are just lonely. To me, neither are a great use of mentor time.

The mentee that has a thirst to learn, a gift for presenting situations with options, a curiosity to experiment and learn gives the mentor a sense of usefulness that is so key. Good mentees have the elements of challenges or opportunities worked out in their minds, but often lack the confidence to make a decision or fear some blind spot they haven’t considered. Those are great examples of where mentoring can really help cut to the chase, or save some dead ends.

The biggest gift you can give someone is to beleive in themselves – AJ Joshi

If you are doing it to make everyone money, let everyone know. If you are doing it for charity, make sure it’s worth it.

 Ah yes, why do we do this. Mentors are rarely ever paid by the hour (though some coaches are, but I contend that is different). I mentor a lot of CEO’s and Founders where I own stock in the company and have quite a vested interest in their success. So by teaching them, I expect to add value to my position. Sometimes, the lessons actually shrink value in the short-term; but that’s why they are called lessons. The worst sin there is to repeat them. Good way to lose a mentor relationship.

But some mentor relationships are just plain charitable. While I have very little free time to take on non-commercial mentorships, sometimes I run across someone who I really believe in, and believe they could use my help. I guess the key point there is that both mentor and mentee know what the other is doing it for, and the ground rules are set and respected.

I’ve been told that time spent and value delivered does not necessarily correlate: you can do just about anything in two minutes… if you spent thirty years perfecting how to do it.


I mentor two kids and several entrepreneurs. Similarities are coincidental.