Conventional wisdom is that as we advance in our careers, we make fewer mistakes.

This isn’t true.

We actually make more of a certain type: smart people mistakes.

These are mistakes we become prone to as we get smarter and think we know things that we actually don’t.

These are hard to catch and therefore hard to fix.

They show up in different areas of our lives and in our businesses practices, such as in relationship building and giving constructive criticism. They especially appear around the topic of mentorship.

The way that a first-time, aspiring entrepreneur should approach a mentor is completely different than how a successful entrepreneur should seek advice.

Yet, many fail to update their approach.

So, I interviewed four millionaire entrepreneurs to ask for their advice on mistakes to avoid.

1. Don’t Ask Conventionally Successful People for Advice

Instead, ask people who became successful quickly and against the odds.

Tim Ferriss, author of The Four-Hour Workweek and The Four-Hour Chef

When choosing teachers (in person or via books, video, etc.), I look for someone who has gone from zero to expert in six months or so. I try to find people who aren’t relying on superior genetics or other unteachable advantages. In other words, I try to find people who use better toolkits or replicable strategies.

Shinji Takeuchi is a great example. He is one of the reasons I mastered swimming after many failed attempts. Unlike most swimmers, he learned to swim in his 30s. He did this by questioning assumptions, rethinking all the so-called “best practices,” and he was able to become an expert in short order as a result.

(via interview on Art Of Charm podcast)

2. Don’t Settle for a Successful Mentor

Instead, ask for help from the world expert.

Brian Scudamore, founder and CEO of 1-800-GOT-JUNK?, You Move Me, and Wow 1 Day Painting

When I encounter a steep learning curve as we grow our companies from $100M to a few hundred million in revenue, I ask for help from my own “mentor board of advisors” (MBA)—a database of about 700 people I know I can turn to for very specific advice.

I always ask myself, “Who is the best on the planet in this hyper-focused area?” For example, if I wanted to improve our culture, I would fly down to meet Tony Hsieh of Zappos for lunch, as I did a few years ago.

I use the following tactics to get in the door with world-class experts:

  1. Ask twice. People like to be asked for help. So don’t be afraid to ask twice, because busy people sometimes need an extra pinch.
  2. Pick up the phone (sometimes). I remember cold calling James Sinegal, founder of Costco, after business hours and being shocked that he answered his own phone.
  3. Personalize your email. Show them why you believe that they are the best person on the planet to help you.
  4. Be super specific. I tap into a very specific skill of theirs, because it’s likely their biggest passion and they want to make time to talk about it.
  5. Be brief. I make my requests short and simple because these people are busy.

3. Don’t Ask Mentors What They Recommend You Do

Instead, ask them what they did in the same situation.

Aaron Steed, CEO of Meathead Movers

When I started my business (now 350+ employees), I was a dumb high school jock—hence the moniker “Meathead.” So, I decided to become comfortable being the dumbest guy in the room by asking for help in various areas. However, in this process, I ended up damaging my relationship with a mentor when he found out that I did not take his advice on how to handle a particular situation.

From this experience, I learned to not ask mentors what I should do, but rather to ask how they have handled similar situations. For example:

Bad question:
I have an employee who wants a raise but doesn’t deserve it. What should I do?

Good question:
Have you ever had an employee who wanted a raise but didn’t deserve it—what did you do?

4. Don’t Fall Prey to the Halo Effect

Instead qualify everybody (including experts) before you ask them for advice.

Benji Rabhan, Founder and CEO Of Apollo Scheduling

When getting advice, many make the mistake of asking experts for advice in areas where their expertise isn’t relevant to the situation or they’re not a true expert in the topic. This is a cognitive bias known as the halo effect.

To avoid this mistake, I recommend taking the following two steps at the beginning of any consulting or mentorship session:

  • Check for fit. I like to open two things: a summary of my goals and a threshold question, such as “Based on what I said, am I talking to the right person or is there someone else you think I should also talk to?” This gives them a socially acceptable way to admit if they aren’t a fit.
  • Make sure they’re a true expert. For any answer I receive from them, I ask them how they arrived at that answer. If I’m still unsure, I ask them why. If they’re truly an expert, they will have direct, objective answers, often based on empirical and historical evidence (most often from first-hand experience).

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