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5 Questions You Should Never Ask Your Mentor

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Do you have a mentor? Do you know what are the best questions to ask and what you should never ask? In this video, I share 5 type of questions to avoid asking your mentor.

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A few weeks ago I was asked by an old high-school friend for business advice.

He was just starting off and was wondering if he should go to the bank and take out a $10K loan to get started.

Fearing a series of bad decisions on his part, I invited him to a Founder's Dinner so he could meet successful entrepreneurs and learn from real world experience…

… not what the people down at the “Business Center” in my hometown were telling him.

During that lunch, he sat quietly and listened super attentively.

Then, with little warning, he broke his silence to ask a dangerous question to one of the entrepreneurs.

“What did you do in the beginning? How did you get started?”

And I was like…

“One second … sorry to interrupt, but I think it’s important that we clarify the question.”

You see, he was trying to learn how he should get started by understanding how they did.

But what he should’ve asked is NOT how they did it….

… but how would they do it today if they were starting over.

It’s a subtle difference that changes everything.

That question – for the purpose of learning – is one example of something you should never ask a mentor.

I’ve got 4 more “faux pas” questions in this week’s video.

Avoiding these questions will not only help you improve your relationship with a great mentor…

… but by asking better questions, you will yield more valuable and practical advice.

If you’re ever lucky enough to have someone take you under their wing and guide you through the challenges of building a company, then you don’t want to ask these questions.

It’s just not worth the risk of losing that person in your life.

My first 3 mentors provided an incredible amount of wisdom and extended confidence in my abilities.

Any chance I get – like this video – I always thank them publicly and honour their contribution to my journey.

So here’s your chance.

Leave a comment with the name of the mentor(s) – maybe the first one if you have dozens – that guided you in your life.

Feel free to tell the story of how they came into your life.

I look forward to reading each one.

Have an incredible day!

With gratitude,

– Dan

Don't forget to share this entrepreneurial advice with your friends, so they can learn too:

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ABOUT DAN MARTELL
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“You can only keep what you give away.” That’s the mantra that’s shaped Dan Martell from a struggling 20-something business owner in the Canadian Maritimes (which is waaay out east) to a successful startup founder who’s raised more than $3 million in venture funding and exited not one… not two… but three tech businesses: Clarity.fm, Spheric and Flowtown.

You can only keep what you give away. That philosophy has led Dan to invest in 33+ early stage startups such as Udemy, Intercom, Unbounce and Foodspotting. It’s also helped him shape the future of Hootsuite as an advisor to the social media tour de force.

An activator, a tech geek, an adrenaline seeker and, yes, a romantic (ask his wife Renee), Dan has recently turned his attention to teaching startups a fundamental, little-discussed lesson that directly impacts their growth: how to scale. You’ll find not only incredible insights in every moment of every talk Dan gives – but also highly actionable takeaways that will propel your business forward. Because Dan gives freely of all that he knows. After all, you can only keep what you give away.

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32 comments

  1. Dan Martell

    Ask a better question, live a better life. This is especially true with mentors. There’s also a series of questions you should never ask a mentor. That’s what I share in this video.

    1. Dario Lascano

      This is glorious, I have been researching “spiritual guidance all rooms booked” for a while now, and I think this has helped. Ever heard of – Banulian Lonameron Breakthrough – (do a google search ) ? Ive heard some amazing things about it and my buddy got amazing results with it.

    2. Alan Park

      Dan, what would you do today if you want to learn more about businesses (not talking about books), but daily operational useful activities so you can build yourself to create a company in the future?

  2. Mzolisi Dywili

    1. Never ask “How did you do that”, ask “how would you start it today”?
    2. Never ask for step by step road map.
    3. Never ask for money
    4. Never ask for a hand out
    5. Never ask them to be a customer

  3. Cynthia McCrea

    Well, that is what the 8(a) government contractor (minority business) Mentor – Protégé program NEVER shares! Your’s was filmed in 2016 and it’s now 2021 and we are all still watching!

  4. Kunal Sampat

    My mentor Jeff has been amazing. He helped me when I had a challenging time at work. I always thought being results driven was all that was needed to succeed. I used to completely ignore people’s perceptions about me or my work. Jeff helped me realize how, at a deeper level, we’re fundamentally the same as humans.

  5. Nick Cuttonaro

    GREAT video Dan!! So inspiring, and inspires me to do a video over business mentorship on my channel. Whats one thing your mentor told you that you still use in your daily work life?

    1. Dan Martell

      Nick, so much… one of my favorites is “Be long term greedy.” – meaning don’t try and take everything out of an opportunity from the beginning. Leave more for others, make money for others and it’ll help propel things forward.

  6. Robert Quinn

    I’m at the very beginning of my journey. This is one of the first videos I’ve watched, in preparation to meet a mentor. I just started attending free pitch nights and meetups at a local startup co-working company. To this point, I have been a fly on the wall. This is solid advice, and I will take it to heart moving forward.

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