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 4 millionaire entrepreneurs to ask for their advice on mistakes to avoid.

Don't Ask Conventionally Successful People For Advice

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

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 thirties. 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)

Don't Settle For A Successful Mentor

Instead, ask for help from the world expert.

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:

Ask twice.
Pick up the phone (sometimes).
Personalize your email
Be super specific
Be brief

Don't Ask Mentors What They Recommend You Do

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

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?

Don't Fall Prey To The Halo Effect

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

When getting advice, many make the mistake of asking experts for advice in areas where (1) Their expertise isn't relevant to the situation or (2) 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.
Make sure they're a true expert


Special thanks to Ian Chew and Sheena Lindahl who volunteered their time to edit this article and do research.