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5 Types of Mentors that helped me go from intern to CEO

Hi all,

Welcome back to Level Up, where people come to win at work.

Let’s talk about mentors. This is going to be a 2 part newsletter series.

Part 1: This Newsletter - the myth of mentors and the 5 types that have helped me succeed.

Part 2: How to attract great mentors and practical tips for finding them.

The Myth of Mentoring

I used to think that having a mentor meant having one person who guides you throughout your whole career.

You learn their skills, you take their advice and (hopefully) shortcut the process that helped them succeed.

What took them 10 years can take you just 5 - with their advice.

The truth is, this unicorn of a mentor is a myth. There is no one “perfect” mentor who can help you conquer all your career goals.


Perhaps, you don’t want the exact skills or behaviours they have for yourself. Maybe you just want 1 or 2 skills they have.

They could have incredible technical skills but have terrible communication.

Or maybe you want to forge your own path - one that no one has done before.

I quickly found out that I needed to reframe how I thought about working with mentors.

I asked myself, ‘how can I engage a mentor to get what I want out of them?’

Now, I have dozens of mentors that I talk to when I have specific problems or questions.

This gives me a diverse set of experiences and data points to craft my own unique pathways.

The 5 Types of Mentoring

I’ve worked as an engineer, product management, CEO, operations manager and many other jobs. Through all of these roles, I have had over 50 mentors.

There are 5 types of mentors I’ve come across - each with their own strengths.

Here is how to make the most of each type of mentor.

The Level 49 Player

Who are they?

This is a person who is an expert in their craft. I say Level 49 because it’s next to impossible to get a hold of the level 100 players because they are time-poor, inaccessible and probably won’t reply to us. So, instead, we focus on people who are very skilled at their craft but have the time and are excited to share their skills.

Ajay, EntryLevel's CEO, reaching out to Elon Musk on LinkedIn. His message reads "Hey man, love your work. Coffee next week?"

Elon, one day we’ll get that coffee and I hope it’s as awkward as all my dreams about it.

This mentor is someone you want to learn a skill from.

Perhaps, they are really good at public speaking.

You want to understand how you can gain that skill.

These people are great to help you fast-track your learning process.

Questions I Ask:

  • “What kinds of resources and tools did you use to learn X?”
  • “Who are the best people to follow for this skill?”
  • “What are some things you would recommend to focus on?”
  • “What mistakes should I avoid making?”

Pro Tip: Be specific with Level 49 players - they know the details of their craft, and this is what you want to dig into.

The Evangelist

Who are they?

We also want mentors who will go beyond advice and open doors for you.

These are the mentors that have a network and can help you find the right opportunities.

Attracting these mentors is hard, but well worth the effort.

Start small, by making real genuine relationships who have similar skills to you.

You’ll be amazed by how many people you can reach just by having 5-10 friends who are in the workforce.

When I was in my first year of university, I went to society meetups and became friends with the 4th and 5th years.

Since they knew people in the industry and other people, my network grew with them and I received opportunities by being connected to them.

Becoming friends with people entering the workforce can be a really powerful thing - just make sure to help others as much as you ask for help.

Questions I Ask:

  • “No pressure, but if you know anyone who would be great to talk to about insights into X, would love an introduction”
  • “Who do you think would be the right people to get help with this?”

Pro Tip: When asking the Evangelist questions, be generous and don't be too direct or demanding.

The Co-Pilot

Who are they?

This is the type of mentor who you want to help you steer your career and learn in the right direction.

Imagine someone in the seat next to you helping you pilot the aircraft across its journey.

These mentors are most helpful when you get honest feedback from them.

So, when you ask questions, make sure they feel comfortable enough, to be honest with you, and don't get too defensive about your work.

Meme of the Rock in a car. He says "I'm doing this to break into data science." The girl in the car says "I've tried that and it didn't work." The Rock looks at the girl, shocked.

Questions I Ask:

  • “Here’s my context and where I’m coming from. XXX, what would you do in my position?”
  • “Here’s a piece of work I did, do you have any feedback? Be as brutally honest as you need to be”

Pro Tip: Getting people to solve your problems can be a powerful tool. It comes down to framing it the right way. I often tell people my context and scenario to see what they would do in my shoes.

The Story Teller

Who are they?

Sometimes, you just want to hear stories and recounts that could inspire you or you could pull insights for yourself.

We know people who are successful but they can’t really explain how they became successful.

When you ask an elite basketball player how they consistently shoot 3-pointers, they just say something simple which might not make sense to you.

Questions I Ask:

  • “I would love to hear how you broke into this space. It’s amazing how you’ve gone from X to Y”
  • “I’m curious, why do you do this job?”

Pro Tip: Get creative, ask some questions to learn more and listen intently.

The Mentee

Who are they?

This one is often overlooked, but you can learn a lot from mentoring others.

There are so many mentoring sessions that I’ve done in the past that end up being a two-way exchange.

Spiderman meme. Mentor and mentee pointing at each other.

I came to mentor someone, but I ended learned so much in the process. Either, I’ve consolidated my own thinking or they have shown me things I haven’t seen.

Try to help others as much as possible and you’ll see things flow back to you.

Questions I Ask:

  • “What are some of the things you want to achieve? What help do you need?”
  • “What kind of people are you looking to meet or talk to”

Those are the 5 types of mentors or mentoring styles I’ve experienced.

Your goal isn’t to have 1 or 2 mentors, it’s to have a network of people you can call upon for different problems and needs.

Once you have a crew of mentors, you start to learn and excel faster than ever.

Here are my parting words to you:

I may not know how to solve every problem, but I sure know who to call when they arise.

- Probably Someone On the Internet

Do you have a question about work❓❓❓❓

Click ‘reply’ and send us your question and we’ll pick 1 or 2 to answer each week! We’ve already started preparing some answers in the following weeks.

Date originally published:
Oct 4, 2022
Date last updated:
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5 Types of Mentors that helped me go from intern to CEO

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