I struggled through young adulthood with a baby face. Nobody gave me any respect – and I don’t blame them – because I looked like a kid. And what does a kid know? Nothing. So, in the social strata of the business world, I was relegated to the “nice to have around but can’t possibly know anything” category.

But when I hit age 30 everything changed. Oh, I still had a baby face, but my genetically dominant predisposition for premature grey hair kicked in. In a matter of months, I went from a hair color that was a shade darker than “desert beige” to something like “bright white.” (Think of Cruella DeVille, but without the black-half of her mane.) All of sudden, people ascribed wisdom to me based on a hair color that is usually associated with people of antiquity. This was a nice change because I had more smarts than my baby face would suggest, but I was far from the wise sage that my grey tresses portrayed.

Years have passed, and now my face has caught up with hair. I don’t yet qualify for the “Senior’s discount” at Denny’s, but every part of my appearance looks like I should be shopping for caskets. I’m not particularly upset by the physical toll that age has ravaged on my appearance because I have finally acquired a modicum of wisdom that might be useful to others. Bottom line: I think that the planets have finally aligned and the circumstances of my life are such that I’ve got something to offer as a mentor.

I’m in the process of mentoring a few guys right now. I meet with them, one-on-one, every few weeks or so. This is not a new process for me because I’ve been in mentoring relationships almost continually since I was in college. But in the past I’ve usually been the mentee. Only recently have I had the opportunity to sit on the other side of the table at Starbucks and assume the role of mentor. At another time I’ll reflect on mentoring from the perspective of the PBM (“person being mentored”). But in this blog, I’d like to offer three key principles for mentoring from the perspective of the mentor.

Let The PBM Come to You.
I know what you’re thinking: you’ve got lots of wisdom, and you’re itching to share it. You’ve learned many lessons the hard way, and you’d like to help someone else avoid the agony that you’ve endured. But it doesn’t matter how many answers you have; you have to keep them to yourself. Put a cork in it until someone asks for your advice. Otherwise, you’ll be guilty of premature exclamation, which doesn’t do anyone any good.

I’ve always stayed away from a mentor that was on the prowl for a protégé. That scenario always has the smell of desperation. Now that I’m more frequently in the role of a mentor, I adhere to that same principal – I don’t initiate the mentoring process (even though I might find many instances when someone is floundering and needs some guidance). Mentoring must be initiated and pursued by the PBM; otherwise, the PBM may lack the realization of his/her need for guidance, and most likely will lack the commitment to stay with the process long enough for it to be productive. Your time is valuable. Use it on someone who is anxious to acquire the wisdom you have to offer.

Let the PBM Set the Agenda
As a mentor, it shouldn’t be your goal to create a “Mini Me” clone of yourself. (Or, if you’re into sports analogies instead of movie trivia, then you shouldn’t be trying to put your number on someone else’s jersey.) Let the PMB set the agenda for your mentoring sessions. Yes, you’ll have to give up control, but this relationship isn’t about control or your assessment of the PBM’s deficiencies. It is about the specific advice that the PBM wants from you, even if you think there is another issue that should be discussed.

Mentoring is not:

- Like a teaching relationship. Your role is not to impart information or instruction. The PBM could find a book or a video to get information.

- Like an athletic coaching relationship. You shouldn’t be trying to improve someone’s skill set (ala golf coach Butch Harmon), and you won’t usually have permission to criticize or berate the PBM’s performance (think Bill Parcells, or if you’re old enough, Woody Hayes).

- Like a “life” coach relationship. You don’t need to come prepared with an arsenal of open-ended questions designed to allow you to tiptoe through the PBM’s mind in an attempt to stimulate self-realization.

- Like being a parent. You don’t need to solve this kid’s problems (even if he is your kid).

At its most basic level, mentoring is straightforward: the PBM is dealing with a set of circumstances, and you’re being asking for your insight. That’s it. Your responsibility ends with the articulation of your perspective on the problem.

Let the PBM Reject Your Advice
With all your wisdom (not to mention the time you invest in the mentoring relationship), it may be difficult to watch a PBM decline to follow your advice. But that is the prerogative of the PBM. Remember that she or he is not coming to you to solve the problem; rather, they want to add your valuable insight into their reservoir of information to help them make a better-informed decision for themselves. You don’t have ownership of the problem, and you certainly don’t have ownership of the PBM. So, don’t be offended if the PBM takes an approach that is different from what you suggested.

If the PBM consistently and continually rejects your advice, then perhaps the mentor/mentee match-up is less than ideal. But don’t consider abandoning your mentee simply because he or she departs from your advice from time to time. Remember, while it is difficult to see your advice rejected, it is even more difficult to watch the mentee follow your advice and then fail because of it.

Wisdom is a lot like manure. It works the best when it is spread around. Mentoring is a way to pass your wisdom along to someone who is anxious to receive it. Grey hair is not a prerequisite, although it will make you appear more distinguished when you’re sitting at Starbucks.

A few months before I started Cedarcrest Capital LLC in 2004 I sat down for lunch with a college buddy who founded E-chalk, a company which supplies a technology platform for schools to link parents, students, and teachers online.

Eager to start my entrepreneurial career, I quizzed him about what founding a company felt like. I think I expected him to tell me about his then four-year venture using words like “Freedom!” “Excitement!”, “Satisfaction!”

Instead, the main word I recall from our lunch was “Ignorance.” Specifically, he related to me a cautionary tale: The best talk he’d heard at a conference on business start-ups he’d recently attended focused on ignorance as the key to entrepreneurship. What the conference speaker meant was that if the average entrepreneur truly knew how hard it would be to build a company, nobody would ever begin. It takes ignorance to want to start a company from scratch.

My friend’s weary look, four years after founding his company, told me he wasn’t kidding. In all my excitement to begin, I’m pretty sure I had no idea what he was talking about.

Shortly after that lunch, I walked into my attorney’s office to begin the process of creating Cedarcrest Capital LLC.

Before I even sat down, he commented to me: “You’ve got the grin of a guy who just quit his job and is starting his own company.”

“Yup!” I said, smiling widely.

He said, wisely I now understand, “You’re going to lose that grin. But hopefully, some day, you’ll be able to get it back.”

The optimism of that meeting has not left me in the subsequent years, but I have certainly had the smugness challenged. Four years since founding my own company, I’ve come to appreciate their thoughts even more.