The Mentoring Roles You Need In Your Life

Some assumptions about getting mentoring

Let's start with some assumptions I'm making.

  • Everyone is busy. Few people walk around with signs on them that say, “I mentor.”
  • No one knows what you need. It's not like you walk around with your own sign.
  • You won't ever get what you never ask for. I know that's a horribly written sentence. Sorry.
  • Given all of the above: you will need to be proactive.

Five mentoring roles you need

The Instructor

The first way to get the mentoring you want is to find someone who has done exactly what you want to do, and ask them, directly, for their help. This is like asking a former quarterback for some help if you're trying out for the quarterback position.

If what you are trying to do hasn't fundamentally changed over time, this approach is fantastic. But that's a big if.

You could ask me about raising venture capital. I did a lot of it in the nineties. Guess what? Everything is different. While some principles remain the same, a lot has changed. So my help won't be very helpful.

The Wise One

If you don't have a specific person who has achieved your specific goal, or if things have changed over time – then that first approach won't be very helpful to you. Instead you need a way to learn and grow without asking for specifics.

I like to look for people who've been doing what they've been doing for a long time. They're bound to have some wisdom that I don't even know I'm missing.

Instead of asking for specific help, invite someone to give you generic and broad, but impactful advice. Ask them to share insights that have had a big part in their own development. Take from it what you will. But trust me when I tell you that there's gold there if you're talking to the right person.

This may not require more than a session or two. But it's remarkably helpful. Often it's a simple truth or question that will rock your world for ages. I was asked, “What would you try if you were guaranteed you wouldn't fail?” and it sent me in directions I never would have guessed.

The Coach

I like to think about this kind of influence like the coach that would take us out to the field for weeks before our sport officially started (in high school). We'd do a lot of running. A lot of drills. A lot of general conditioning that would help us perform better when things finally started up – because we were in better shape.

Look for someone that has a program. A routine. A set of questions that have proven useful and a set of exercises (homework) that can get you working on stuff that you've been ignoring.

Often your blind spots are where they work best. Because they'll get you and your future in shape.

What's great about coaches is that you can hire them for different kinds of objectives you have – from learning new disciplines to tightening up things that you know are a bit soft.

The Analyst

You've used Google Analytics right? Now imagine it was a person. You know, the kind that tracks a lot of your data and then – out of all that massive amount of data – asks you the single question that turns it on its head and makes you rethink everything.

I was once asked, “What would it take for you to hit all of next year's projections this year?” – what the what??

But it was an interesting and challenging question. These days if I find myself working with someone who's really smart, I ask to look at their data, because I know two things:

  1. They're likely to know all the other generic wisdom I have for them
  2. The data is likely to show me something that they've missed because they're hip deep in things

So, as you talk with people, listen for the people that ask you questions about metrics and data measurements. They're likely to be drawn to those kinds of conversations and may be able to help provide some quick insight, if you have the data.

Again, another big if. Make sure you're collecting data on every aspect of your professional life.

The Personal Trainer

I use the metaphor of a personal trainer because it's one people understand. But I hate them. Let's just get that out of the way. I hate them for the very reason I recommend them. They're always motivational. They're upbeat and praising things.

And frankly, if I'm sore, hurting, and in pain (yes, they sound the same but to me it's bad enough that they get three words), I hate cheery people. But that's just me.

The reason this role is so critical to your success is because making changes after insight has arrived isn't always easy. You have routines. You have processes and structure that are designed to reinforce the old way of doing things.

So finding someone who reinforces the new way is well worth your time and energy. Find someone upbeat. Cheery even. And someone who can help motivate you, however you need it, to keep making the changes you need to.


You're likely to ask me which one is right for you. The answer is any of the above. Or all of them. All together. Or in series. Or just one. The answer is that it's up to you. I've had people in my life fill every one of these roles. And I've worked in each of these capacities with some of the folks I've mentored over the last twenty years.

There's no perfect answer.

Except not getting any help at all and staying stuck in the same routines that will keep delivering the exact same results as always. If you want new results, better results, then start looking for these five mentoring roles.