Maximize Your Mentoring: 10 Fundamental Rules to Make The Most Out of A Mentoring Relationship

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Mentoring can play a HUGE part in your personal progress.

Having the courage to ask someone to be your mentor can be tough.

It’s tougher making sure the mentoring relationship goes smoothly.

(If you get the yes!)

That’s why I broke down 10 Fundamental Rules to make the most out of a mentoring relationship.

Check them out below.

Rule # 0: Mentoring is a BIG commitment.

This rule comes BEFORE any other rule!

Why?

For you to truly understand —as a potential mentee—the PRICE of what you are asking for.

There is a common misconception regarding mentorship.

Where people think they’ll just as a potential mentor:

“Hey will you mentor me?”

and all of a sudden all the mentor say “Yes!” and BOOM all of a sudden you know everything they know!

That’s just not how it works!

Mentoring happens ONE conversation at a time.

In small UNITS of conversation.

GRADUALLY!

You are taking your prospective mentor UP a commitment ladder.

One rung at a time.

You can always crank up the speed (on a case by case basis)

Here is a rough sketch of the ladder:

THE MENTORING COMMITMENT LADDER

(ordered from low to high commitment)

RULE #1 : Be specific.

Part of what makes a mentoring relationship successful is:

the ability to ask questions that your mentor has ALWAYS wanted to answer BUT doesn’t get a chance to.

Why don’t they get a chance to share?

Since, they don’t have a HYPER-ENGAGED mentees.

Like You!

Thus, a BEAUTIFUL opportunity!

You are getting information that ISN’T in a textbook.

That means, with each passing conversation you are GAINING a competitive edge!

NOTE: working into specific questions will take some time. Because you need to know about the field.

This exercise below will help.

RULE # 2 : Do your homework.

“Chance favors only the prepared mind.”

Luis Pasteur, genius scientist who discovered vaccines

Doing your homework for mentoring is VITAL!

WHAT THIS REALLY COMMUNICATES:

• You are empathetic!

• You are in their shoes!

• You understand the world through your mentors eyes.

Such as:

“WOW! There are a lot of people trying to get in contact with me.”

“How do I know which people are worth my time to invest in?”

“Will this person that’s asking me to mentor follow-through?”

“There are A LOT of people who make the big claim they’ll do the work.”

It SHOWS your prospective mentor you are willing to do the work.

[NOTE: If you want to understand you mentors perspective better, here is an excellent Harvard Business Review Article: What Mentors Wish Their Mentees Knew.]

Since PEOPLE that reach out to them ALL THE TIME!

They’ve seen people “come and go.”

Make big claims.

Then fade off into the night.

HOWEVER, YOU are different.

Because you simply DID!

[Double Note: If you are looking for stuff to read before you meet with your mentor, check out this entrepreneurship reading list I put together.]

PERSONAL EXAMPLE: Connecting with coincidence

There was a particular expert I reached out to.

WHY? I was CRAVING for answers!

So…I cold called him.

BUT before I called…

• I read ALL of his books. (Listened via Audible.)
• I took notes.
• I even had references to specific passages and page numbers.

He didn’t pick up my phone call.

I was disappointed!

Thinking all that work had gone to waste, I was frustrated.

After a nerve-wrecking 24 hours, he called back.

I was prepared for the call!

I got the answers I was looking for AND then some!

Doing the prep work lead to:

• Paid Consulting Agreement
• lifelong friendship
• Guest Podcast Interview

Had I not been that prepared, the conversation would not have occurred.

Had I not read the book (and “done my homework”.)I could have easily missed that synchronicity/ coindience to connect.

Listen to the cold call story and how I ended up on his podcast here.

ALL that work paid off!

RULE # 3 : Perform.

The strength of the mentoring relationships is BASED on performance!

Take the information they give you and DO IT!

You MUST perform!

That means taking your mentors advice and getting results.

Thus, only ask for said advice when you are ABSOLUTELY CERTAIN you are ready to move forward!

Not a second before.

Because you will be dangerously wasting you time and the time of others.

Another key factor of performance is: PERSONAL GROWTH.

Your mentor will watch you grow over time!

Improve and form into the person you want to become.

Ensure you are doing that because that a big part of the journey that’s fun!

RULE #4 : Make it EASY for them.

The easier it is for the mentor, the more they will share with you.

Lower the friction for sharing.

EXAMPLE: In-Person Meeting

For an in-person meeting, bring the following:

• Notepad. for both parties to write on.

• 2 pens. In case your mentor wants to use one.

During the in-person meeting:

• Write stuff down and take notes FOR them.
• Draw diagrams summarizing some of the info.

DO NOT make your potential mentor type shit out for you- you’ve become a hassle for them.

Unless—they like to write.

The easier you make it for someone to SHARE knowledge with you and ACT on it, the sooner you’ll progress through mentorship.

pro tip: Send calendar invites

Know how to send calendar invites!

It’ll make your mentors life easier.

Here are tutorials.

• Google Calendar. How to Send a Google Calendar Invite
• Outlook. How to send a calendar invite in Outlook in 5 simple steps
• iCal. Invite People to Events on Your Mac

RULE #5 : Don’t ask questions to answers that can be readily found.

WHY?

It is a waste of your time AND everybody else’s time around you.

Show that you’ve followed Rule 3: Do your Homework.

You look for mentorship ONCE you’ve gotten past implementing the typical answers.

EXAMPLE: ASKING TIM FERRISS FOR ADVICE (SIMULATION)

For example, imagine you get a chance to ask Tim Ferriss how to write a book. A subject that he’s covered on many occasions. and you expect him to stay on a 1 hour call with you. —instead of redirecting you to the following posts:

• How to Write a Bestselling Book This Year

• How Authors Really Make Money: The Rebirth of Seth Godin and Death of Traditional Publishing}

That would be delusional!

INSTEAD: Come back having tried the idea getting results and asking for more detailed feedback.

note: if you don’t want to read “all” of their stuff then they might NOT be a good mentor for you.

RULE #6 : Do your own independent reading.

You MUST be reading/learning outside of your mentoring.

To be prepared FOR your mentoring.

Do not expect your mentor to teach you everything about their field.

It’s unrealistic!

Read industry-specific books.

Not just random books—outside your.

Treat mentoring like an Independent Study!

Independent Study defined as:

…a planned research process that (a) is self-directed, (b) is similar to one used by a practicing professional or is authentic to the discipline; (c) is facilitated and monitored by the teacher; and (d) focuses on lifelike problems that go beyond the regular class setting.

THE BENEFIT OF TREATING MENTORING LIKE AN INDEPENDENT STUDY

• Ask Better Questions. You’ll be able to ASK better questions.

• Learn Faster. You’ll have information to hook experience on to. Thus, you’ll learn A LOT faster! That’s why they suggest 2 years of experience BEFORE an MBA program. Experience you can grasp.

• Offer Value. You may stumble across things your mentor does NOT know and you share it with them. Subsequently, helping them start a new vein of research.

• Speak the language. By studying on your own, you’ll learn the language faster of that field.

Going back to being specific.

The more you KNOW about the field, the bettter the questions you can ask.

Yes- is it a lot at once? YUP.

However if you nail it- it’s worth it!

Ayou are learning A LOT more information at once.

You’re gonna go off and learn stuff and then bring it back to them.

That’s VALUABLE!

In the above definition; THEY are the teacher.

They are helping you progress and move forward and facilitating your learning.

LEARN!

RULE #7 : Be prepared to share snippets of your story.

Your mentor will eventually (if all goes well) be interested in part of your story.

Just like the great Dale Carnegie said, “to be interesting, be interested.”

Asking you elements of your story.

Elements such as:

“Why are you doing what you are doing?

“What is driving you forward?”

“Why have you become interested in this subject?”

Why Snippets versus the full story?

You don’t want to data dump.

Emotions can overwhelm a mentor.

Because they are REALLY listening.

Really listening to every word is hard work!

Will you show emotions with your mentor—absolutely.

Have certain snippets they can grab on to first!

You aren’t going to POUR OUT your story.

RULE #8 : Pick up the check.

PERSONAL RESISTANCE: “WHAT IF I CANT AFFORD IT?”

If you are just starting out and can’t afford lunch that’s fine!

Pick a coffee spot.

If you can’t pay for lunch, bake. Bring it with you.

Make something.

Your mentor may pick the place.

THE RATIONALE:

Reciprocity.

This dynamic can change over time. However, allow you default position to be—pick up the whole tab 1st!

RULE #9 : Always be ready for the quick call.

”Hey! do you have 5 minutes?”

“Hey! do you have 15 minutes?”

“I’ve got 20 minutes before my 5 o-clock. Let me call you then.”

“I’m in town these days. Are you around to grab lunch?”

“Do you have time to chat?”

All the above are potential real-life scenarios you’ll encounter with a mentor.

(Trust me. I would know as I’ve experienced all of them.)

Be ready to drop what you are doing and run!

If you picked your mentor correctly, take whatever chance you can to gain knowledge.

Take it!

Short of medical emergencies, book it.

• Show up early.
• Stay late.
• Have a parking spot picked at ready for them if you have too.
• Carry a notebook with you at all times.

My go-to notebook.

Picture of notebook.

A simple, direct relationship.

RULE #10 : Rarely reschedule.

Rescheduling often is an insult to the mentor.

If they were important enough to reach out to, but not enough to meet with- that’s just going to lead to bad juju.

If you have to reschedule, aim for ATLEAST 48 hours heads up.

Anything before that better have a damn good reason.

BONUS RULE #11 : Make ways to Make Your Mentor look good

This is an advanced concept.

One that you think about AFTER you’ve developed an in-depth relationship.

Once you’ve developed a long-term mentoring relationship, you are searching for ways to make THEM look better.

Find wins for them.

3 Wins you can think about

• Sharing new technology. It helps make their processes easier and faster! (e.g Roam Research)
• Bring them into consulting projects. Bringing dollars in always helps (and or impact!)
• Connect them with key people. Key person you know that you mentor wants to meet that you know? Make the connection!

BONUS RULE #12 : As you grow, reverse mentor.

When you know more than your mentor (in an area), teach them!

Reverse mentor!

Reverse mentoring defined as:

…reverse mentoring is to share expertise and skills with “older” people who need such competences and to build a community whose members support each other.

Article: Effectiveness of reverse mentoring in creating intergenerational relationships, Journal of Organizational Change MAnagement

In this case, I turn “older” as the person with less experience in the area you can reach them in.

For example: I was able to share a graph database called Neo4J with a mentor and he’s sharing an amazing list of sociology reading books.

I was SO excited to reverse mentor!

Because of how much information he has (and continues to) share with me.

Do the same.

• Tool your mentor up.
• Help them level up!
• The added benefit: It just levels up the people around you sooner!

NOTE: A SHIFT IN POWER DYNAMIC

Tread into reverse mentoring— delicately!

Since there is an EXISTING power dynamic there.

By reverse mentoring, you change the asymmetry in the relationship.

It goes from lop-sided to balanced.

Heres a proven word-for-word script:

“Hey [Mentor Name]! I’ve got something cool that I’d like to show you that I think you’d be interested in! Because it connects to [conversation topic we were talking about].”

Bonus: How to reject advice from your mentor

There will be moments where your mentors advice pushed you to clarify your own perspective.

Where you are picking your way.

That’s okay. You just need to be able to do that politely.

Here is an excellent article from Adam Grant talking about : How to Reject Advice Without Alienating Your Mentor

Great language:

I’ve collected some conflicting stances on this—would love to discuss and hear how you’d approach this dilemma.“

To be honest, that’s not what I was hoping you’d say. I know it wasn’t easy advice to give, and I need to reflect on it. I appreciate you looking out for my best interests.“

Although I didn’t end up going the route you suggested, you pushed me to clarify my priorities, and I’m thankful for your time and insight.

RECAP

Mentoring can be a foundational cornerstone for success.

If you leverage it and prepare accordingly you can have a DISPROPORTIONATE advantage!

Be ready and be prepared for that!

Be prepared by following the rules above!

Leverage and practice them.

You’ll thank yourself when you do!