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🤦 The Biggest Mistakes People Make When Finding Mentors

Here we continue the series on mentoring!

I’m super mentor-able.

Not sure if that’s a flex but I’d like to think it is.

Somehow, I’ve been able to find and attract amazing, world-class mentors to help me on my journey.

Hope you enjoyed last week’s edition about the 5 types of mentors that helped me go from intern to CEO over the last 10 years.

Check it out here. (My mum told me it’s really good and she’s never lied to me).

Initially, we said this would be a 2 part series but due to popular demand, we’re extending it a little more. This week, we talk about how to attract mentors and next week, I’ll go over some growth hack style tactics and specific examples on messaging people on LinkedIn etc.

The Sweat of Desperation 😰

Before I go too hard in finding mentors and spamming people on LinkedIn, I think about what exactly I want to achieve by meeting people. An easy way to start is to think about what questions you want to be answered.

The worst way to start this search is to start by asking them for jobs or trying to push them for introductions.

The worst time to start reaching out to mentors is when you are ready to start a new job.


It’s been known for a while that in dating scenarios, people who are desperate for a partner give off a ‘sweat of desperation’ which makes them less desirable to others.

When you project desperate energy to others, it can often lead to poor results.

In this article, I’m going to show you how to find great mentors, and show you how NOT to give off the sweat of desperation 😰

Great Things Attract Great People 🧲

Most of my mentors come to me when I’m not actively looking for them. I’m simply building something interesting, and people find me and reach out.

Most of my mentors, investors and even team members at EntryLevel have found me because they like the work that we do.

While most of us won’t start companies, doing great work can attract great people to come help you.

How do you attract great people?

Well, perhaps you share insightful posts on LinkedIn. Or, you publish a little project you’re tinkering with. These are small things that can help attract great people.

I find that when people share their projects and message me asking me for feedback or thoughts on it, I’m more likely to help them. Their approach is specific, actionable and easy for me to engage with.

In summary, go build something, or work on a project or portfolio that can attract people to help you and give feedback.

Passionate Listener 🎧

Mentors are people.

Many people like to share their stories and talk about themselves.

If you build your listening skills then people will want to talk to you and tell you more.

Being great at responding and excited about what people are saying will make them think “wow that person was amazing, I want to talk to them again.”

I’ve done calls with people where they have said very little, and I thought ‘they’re a great person, I should chat to them again.’

If I’m getting mentored or supported, I’ll try and talk as little as possible. You can do this by asking great questions.

Ask Great Questions 🤔

Good Question

Asking great questions is difficult.

Being able to ask questions in a way that makes mentors excited to answer and allows you to pull actionable advice will improve your ability to learn.

Daniel is our Product Manager at EntryLevel. One of the traits that made him stand out early on was his ability to ask great questions and made me feel incredibly listened to.

We’ve not worked together for over 4 years across 3 separate companies.

Here are 3 things Daniel does that I’ve noticed:

1. He asks specific questions over vague ones. When he asks me for help or advice it’s very specific and actionable. It makes my life easier to create an answer and it gives him actionable advice. Here are some questions from our chat log:

  • “When I create a new feature request, how should I go about finding the relevant stakeholders?

  • ”How can I get a team member on my side, if they disagree with my action plan? It’s about the situation with … X”

2. He’s prepared and knows what he want’s to ask upfront. He’s thought about what information he wants to gather and the questions he wants to ask before going into a situation

3. He avoids leading questions & strict scripts. Daniel asks questions in an open-ended way and doesn’t try to force a judgement.

For example, he wouldn’t ask: “I’m building a product strategy document and I’m going to do it this way. What do you think?”These types of questions could be good for feedback on work. But, if you’re trying to figure out the best way to do something, you don't want to lead with a question where the response could be “Yes, that looks fine” Instead, he will say: “What do you think are some resources I could look at for building a great product strategy?” OR ”How should I go about making a product strategy for the EntryLevel Platform?”

Be like Daniel. Ask Great Questions.


Speaking of which… do you have a great question for us? Treat us like a Mentor!

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 for the following weeks.

We’re stockpiling some great questions that we will be answering in a future community newsletter.


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We promised you some practical tips. Stay tuned for next week when I go through some of my exact tactics for reaching out to people.