Last month I gave a talk at Innovate Pasadena on mentoring. I shared some reflections on what it has meant to me to have mentors in my personal and work life, and what it means to me to be a mentor when I have the opportunity. I talked about my former staff members who still call me up, the new people whose journey I have joined, and how all that creates an ecosystem of mutual support, vibrant feedback loops, and trusted opinion testing.
It is worth noting given the inescapable subjectivity in this meditation that this is simply how I think about the world, one mentor’s opinion as it were, and not meant to be an encyclopedic statement for all worthy mentors at large. That said, here are some of the key ideas I covered:
What is mentoring? My definition: One person who has ideas and experience to offer engaging in a relationship with another person who has ideas and experience to offer. It’s a two-way street. If it’s not a relationship—which means give and take—it does not work.
What isn’t it? It isn’t me making the hard decisions for you that you don’t want to make for yourself. I think of this as a Socratic dialogue where I get to ask you a lot of questions. You’re going to do all the work, because it’s your work, and I won’t let you dump your work on me.
Am I going to step on your fingers or tell you you’re awesome? Yes. It depends on what you need. This is jazz. I go with the flow. BTW, if you’re not awesome, I’m not going to be interested at all. If I’m hard on you, it’s because I need to be, not because I want to be. If I don’t say anything at all, it’s because I have given up—that’s the worst thing that can happen.
What’s the difference between consulting, coaching, and mentoring? I have given a three-day seminar on this, but think of it this way: When I’m consulting, you’re paying for my experience to fix a problem; you want a recommendation and you want it backed up. When I’m coaching, you’re paying me for my time to bring out the best in you. I think of both consulting and coaching as relatively shorter-term assignments that surely can be extended, and while mentoring encompasses elements of both, I think of it as a longer-term engagement, even if sporadic. When I’m mentoring, we’re both investing in a relationship that helps you do your job, that brings both of us benefits, tangible and intangible. I don’t expect anything when I consult except to get paid on time, which is why I don’t do much of it. I don’t expect you to give back when I’m coaching, I expect you to perform. When I’m mentoring, I expect to get something back from you, even if it’s just satisfaction, but I also expect to learn things from you that I can redirect elsewhere.
Can your boss be your mentor? Yes, if you are very lucky. I’ve had a few bosses who were fantastic mentors. They were 100% in my corner. They were not competing with me. I have also had awful bosses who said all the buzzwords but couldn’t have cared less if I lived or died as long as I made them rich. If you don’t have a good boss, and odds are you don’t, especially if you’re an entrepreneur, then find yourself a mentor. I promise you, the mountain climb ahead is going to hurt a lot less if you have someone who really cares about you—other than your spouse, who is truly tired of hearing all your business problems and probably can’t help you more than she or he already has.
How do I find a mentor? They will probably find you, and the question is, will you be paying attention? Almost no one fills out a mentoring application or posts a listing on Craigslist to be a mentor. Coaches and consultants do that. Mentors opt into a relationship as it naturally expands. Keep your eyes open! If someone is taking an interest in your work, go with it. Incubators and accelerators offer formal and informal ways to meet industry experts, but so do community centers and shared-interest groups. If someone invests in your company and he or she is showing an interest in more than your financial performance, spend more time with them. Do things for people all the time and they will do things for you, often when you least expect it and most need it. You don’t have to ask, “Will you be my mentor?” In fact, most of the time I find out years afterward that someone thought of me as a mentor. It happens naturally.
Will I open my Rolodex to you? OK, first, what’s a Rolodex? The answer is yes, selectively, as trust builds. If I’m financially invested in your success and I think you’ll do well with an open door, I may open it. If I’m not personally invested in you but I think there is a win-win introducing you to someone I know, I may do it, but understand, my network and my reputation are among my most important assets, so if you take advantage of my network, it’s one and done.
Do I get compensated? This can be tricky. Sometimes there is money involved in mentoring, sometimes not. First and foremost, if I admire your commitment or like what you’re brave enough to be attempting, I just do it because thank goodness someone did it for me. I have about 200 or so people from past gigs whom I still call back for free. If you worked for me in the past and reach out to me and you weren’t a turd, I’ll always call you back promptly. Sometimes in a board situation I might get paid something meaningful at liquidity. Sometimes if liquidity is a long way off and it makes sense for everyone involved given the time commitment, I might take a retainer fee. Often I get involved in a project on pure spec with the vague potential of phantom equity. A lot here depends on how much sequential time is involved, as well as how curious I am about your vision. Free or paid, cash or stock, what matters is that we both feel good about it, that the material and spiritual rewards all feel fair, and we are always transparent in our expectations.
Do you have to listen to your mentor for it to work? Yes, you have to listen. You don’t have to do what I say, but I have to know you’re listening. If you’re not listening, then why am I talking? If you just want my contacts or my money, I’m not a mentor, I’m something else. If I say something and you decide you don’t want to do it, that’s cool; just explain your thought process so I know that we are in this together. If you blow me off or don’t afford me that level of respect, I am going to bail.
Must you pay it forward and backward? You must. If you’re not planning to help someone down the road, don’t expect to keep my interest. Good people attract good people. If you join this club, expect to stay in it for life.