MentorMost people have this vision of a mentor being this friendly sage who dispenses wisdom in hushed tones just when you need it.  And that can and does happen. But I get asked a lot how to foster mentor relationships, and I offer perhaps a slightly different perspective on the value of a mentor.

About 15 years ago, I got really lucky.  I had two people come in to my life and business who both ended up being mentors to me.  The main reason I was (an am) lucky was not the timing, it was the fact that both of these mentors were very direct in giving me feedback.  That’s a skill and discipline that is harder to find, and these two men had it in copious amounts.  As soon as I would outline a challenge and then begin the (inevitable) process of self-defense and looking for solutions everywhere but within, they would call me out:  ”Why do you say that?  What are you doing about it?  How would you think that would be a solution?” These are all questions that I refused to ask myself.

These have been some of the greatest learning moments of my life. The value of a different perspective well-delivered is huge.  The mentor has to be willing and able to challenge you when you are hedging (we all do), call bullshit when you’re bullshitting (yup, we do that too) and help you work through the step-by-step process of changing.

Here’s a quick, recent example of the value of a mentor.  One of my mentors asked me to come to Canada to deliver an evening talk to a client of his.  This is a talk I’ve delivered probably over a hundred times.  But luckily, he was in the audience for the talk and listened along with the customer.  After the talk, we thanked the client and got in the car to go grab a beer.  Before he put the car in gear, he asked me, “What’s one thing that you think you did well?”  Not only did I answer this question, but he had an answer as well. Then he asked,“Now, what’s one thing that you would do differently?”  At this point, I knew what was coming…he was going to point something out.  And he did.  He said, “You have some key content in this talk, but there are a few items that are just out of order.  If you re-order them, they will be much more powerful.”  As we talked about it, it dawned on me that, in a talk I have given tons of times, there was a huge, simple improvement I could make.  And on the next talk the following week, I made that change and could immediately detect a more powerful impact on the audience.  It seems like a small thing, but it’s not.  THIS is how change and learning and improvement happen.  Without him, I’d still be giving that talk the same way.  But a strong mentor can help you take the good in any game you are playing and make it great.

Now that you know the value of a strong mentor, how do you actually go about finding one? Here’s a quick attempt to translate an organic process to a linear one:

1. Think about the people (teachers, colleagues, investors, friends) who have had an influence on you.

2. As you narrow your list, think about the similarities and differences these people have with you.

If they are too close to your perspective, scratch them off the list.  If they have had different leadership roles and life experiences than you, move them higher on the list.

3. Set up a call and ask each of them three key questions:

  • Would you gain value from helping me solve occasional challenges that I’m facing in my work?
  • Would you be available for a conversation once a quarter over a sustained period of time?
  • Would you be able to give me direct feedback without pulling punches?

4. If one of them agrees, suggest a conversation where you bring a challenge to the table.

If that conversation includes perspectives you haven’t considered and it makes you a little uncomfortable, you have probably found a great mentor.  If not, keep trying.

5. Send a thank you note, as a conversation like this is a gift and should be acknowledged as such.

Beware: if you’re not ready to accept criticism or change how you approach certain problems, you probably are not ready for a mentor. But once you are ready, choose wisely and get ready to learn a lot about yourself.

Craig Wortmann is the CEO of Sales Engine, a company that helps firms build and tune their sales engine. In his spare time (that’s funny!), he teaches entrepreneurship classes at the University of Chicago’s Booth School of Business. Don’t be afraid to connect with him on Twitter or LinkedIn.

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