Shaun, my Uber driver this morning, grew up in Atlanta. He had a smooth, caramel-colored complexion and a voice to go with it. He was young and instantly likeable. What made him likable? I’m trying to figure that out.

He was a talker. I don’t normally warm to talkative drivers because I like to spend my commuting time working. But Shaun talked because he was curious. He asked questions, all kinds of questions. And he asked as if he were really interested in my opinion.

He told me how he ended up in LA (on a whim), how he was working two jobs (to save money to start a career). Then he asked me all sorts of questions about what kind of career I would recommend.

I was charmed by his total lack of bravado (which I would have expected from a man of his young age) and his trust in me.

When we arrived at my destination, I wanted to keep talking. Heck, I wanted to adopt him. I gave him my card. I have a good feeling about him. Maybe one day he’ll give me a shout, ask me a question about his career. Maybe one day I’ll be able to help him.

Achieve More in Your Career – Faster and Easier – With a Mentor, Part 2 

It was 1983 – the first “Financial Newsletter Publishers’ Roundtable,” and I was representing a small but up-and-coming publisher based in South Florida.

During the last several hours of the otherwise convivial meeting, the discussion turned towards the “immorality” of selling subscriptions for $49 a year. People were upset. Some were livid. And their ire was directed towards me.

It was confusing. Embarrassing. I felt like I was being ambushed.

What I didn’t know going into the meeting was that the $49 that we were charging for our newsletters was half that of what everyone else was charging. They felt that we were trying to break into their market by discounting our prices. They were right. But I didn’t expect them to care.

After the meeting ended, I was in front of the hotel, about to get into a taxi to take me to the airport, when one of the attendees came up behind me and asked if he could share the ride. I agreed, mentally preparing myself for a lecture. None came. He talked about the weather and the meal we had for dinner the previous night. Finally, I had to interrupt him and ask him why, considering the way I had been attacked in the meeting, he would want to ride with me.

“Oh, that,” he said. “Don’t worry about that. It’s just politics. There is business and there is politics. Politics is bullshit. We are going to move to the $49 price next month. You guys have done a great job with it. People gripe in public, but in private we don’t pay attention to any of that.”

I can still remember the feeling I had. I couldn’t believe that he had been excoriating me a half-hour earlier, and now he was saying he was going to follow our lead. It was a watershed moment for me. I knew I was learning something important, something I would never forget.

There are hundreds of other brief conversations I’ve had with friends and colleagues and strangers that gave me new insights and ideas about my businesses or my role in business – each one a lesson that had immeasurable value to me as I moved forward with my career.

In Part 1 of this essay, I talked about traditional mentorships – where an experienced businessperson works closely with a younger person for a long period of time.

Today, I want to talk about this other type of mentorship – the conversation you have with a speaker at a conference or an author at a book signing or a guest at a wedding… or any other chance encounter.

For lack of a better term, let’s call these experiences – solitary and removed as they may be – transactional mentorships.

Chance Encounters Can Change Your Life 

Is it possible to accelerate your progress in your career by increasing the number of such experiences?

I think it is. Moreover, I think it’s possible to develop a “bullpen” of smart, powerful, and influential players in your industry that you can call on not just once but whenever you need help.

I’m talking about people that would normally be unapproachable.

It can happen. I’ve seen it happen. It’s happened to me. But it can also go badly wrong. To develop your own A-Team of supporters, you have to do more than collect phone numbers. You have to spend some time to figure out a good reason why each one might want to help you. In other words, you have to make the relationships fair. You have to figure out a quid for the quo.

The Quid Pro Quo in a Transactional Mentorship

As I explained in Part 1, “Traditional mentorships work because the benefits of the relationship are shared. The mentee advances his/her career by following the good advice of the mentor, and the mentor shares in the increased value of the business as the mentee contributes to it. At the same time, the mentor has the satisfaction of helping someone else succeed, while the mentee has the comfort and support of someone with power and privilege.”

A transactional mentorship is a different kettle of fish. Since there is no common business interest between mentor and mentee, there’s no natural quid pro quo either.

But you can create one.

At a business conference, industry event, book signing, and so on, experts come expecting to answer questions. “Paying” for the answer you get is as easy as prefacing your question with a compliment – telling the expert something specific that you liked about his book or his speech or his business. Although doing something so obvious may seem cheesy to you, it won’t come across as cheesy if you say it with sincerity.

You can make the same sort of ego payment on paper or in email: one specific and sincere compliment followed by one specific and sincere question.

Note: When I say make the compliment specific, I mean specific to that particular person, to his particular career, or to a particular accomplishment of his.

And when I say make the question specific, this is important. The compliment will let him know that you admire him. But it is the question that is the quid for the quo, because it gives him the pleasure of solving your problem or otherwise giving you his advice.

As someone who has played the role of transactional mentor countless times, I can attest to the fairness of the deal. I’m always flattered to be asked and happy to answer questions, because it makes me feel good. The transaction is balanced. It’s a win-win.

Making the Most of a Transactional Mentorship 

Having a brief interaction with an expert in your field can be extremely valuable. Even better is to convert it into something more.

How is that done? That’s the million-dollar question. And there is no single answer. We are talking about building a longer-term, balanced relationship when the obvious factors – knowledge, access, influence, and wealth – are all on one side. And it’s going to be different for every potential mentor on your list.

This is what I recommend…

You begin with that first contact. It could be a chance in-person encounter… or it could be a quick email that you send to your prospect. You say something specific that is complimentary. And you ask a specific question. (If you’re doing this by email, you can expect to get an answer 20% to 50% of the time.)

Follow up with a personal thank-you note. Make it a handwritten note. Thank your prospect graciously, but don’t go on too long. Insert your business card. It will probably be tossed, but it will be glanced at. And that will increase the chance that he will remember your name.

After you’ve had a chance to implement his suggestion, write to thank him again and to announce the good news – that it has had some positive effect on your life/career. Keep this note brief, as well. And specific.

A month or two later, contact the prospect again. This time, you can do it via email – and this time, he is almost certain to remember who you are.

The purpose of this contact is to remind him of the great help he has already been to you… and ask for a quick personal meeting to talk about your career. In his office, if possible – or, if he’s located out of your local area, via a 15-minute phone call.

If he agrees, and you get along, you’ve got yourself an “occasional” mentor. An important person in your field who would be willing to take your call or respond to your email whenever you have a question.

How great would that be?

What to Expect From This Relationship

Keep in mind: This is not a traditional mentorship where there is a financial quid pro quo in place. With occasional mentorships, there is natural imbalance. The mentor’s reward will always be something he or she can do without, so it’s going to be difficult to maintain equilibrium. There will always be a tendency towards entropy. It will be the rare occasional relationship that continues for years.

Compensate for the fragility of the relationship by having not one but a half-dozen or a dozen people on your occasional mentor list.

Be polite. Be complimentary. Be specific. And be thankful. Make it a habit and your career will take off.