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If you don’t have someone regularly challenging your thinking my recommendation is to get someone to fill that role … today.

It could be a friend, a peer or a mentor. Or, as you’ll see below it could be someone you have never met and will never meet.

I’m sure you are finding that your boss, your customers, and your partners will regularly Challenge Your Thinking. What I’m suggesting here is you have somebody outside of that network of contacts to challenge your thinking too.

I have a few suggestions below to help. Including Informational Interviews.

Mentors fill this role well

A lot of people don’t think they have mentors. And, in the classic traditional sense they might be right. But, people that have friends that Challenge Their Thinking on a regular basis could be considered mentors. Appreciate them for what they provide for you. Often times at no cost to you. Except sometimes to become completely exasperated with their non-stop questions.

Build on that! Ask them for more.
Ask them to Challenge Your Thinking

What does Challenge Your Thinking mean?

It means everything from just asking you to vet your assumptions to as deep-of-a-dive as you want. It’s better to go deep with a friendly audience that is willing to allow you to flounder a bit.

  • It can be everything from asking for how you came up with an idea and where you expect it to end up.
  • It can be a series of tough questions about where you got your data and how you’ll prove your assumptions.
  • It can be dependent upon how much time you want to put into it and how much ideational energy you want to put into it.

Brutal Honesty

Someone challenging your thinking can really put you to the test. They can push you and your thinking processes to verify that your ideas hold water. Ask for and expect … Brutal Honesty.

Brutal honesty is tough love. But it’s worth it.

These two words came from a friend, peer and mentor in my early days at Microsoft. And he meant it. And, he would expect it in return. He would expect me to challenge his thinking too. Brutal Honesty is a two way street.

Challenging Your Thinking in the Real World

There are options available to you today that allow you to Challenge Your Thinking indirectly using online options, social networking and even interview loops.

Online, On-the-Phone and In-Person Options

  • Interview Loops – I can tell you from personal experience that Amazon does an amazing job asking tough questions that get you thinking. Amazon has a data driven culture and if you cannot quantify your thinking … you are sunk. Even if you aren’t looking aggressively for your next role it’s worth it to evaluate some roles that look interesting. Use them as Informational Interviews to Challenge Your Thinking.
  • Quora, Medium and Reddit – All of these tools serve a slightly different, but somewhat overlapping purpose. You can ask questions, you can research ideas and answers, and you can submit your own thoughts. Use them to Challenge Your Thinking.
  • Use The Socials – Yes, you can use the social networking tools like Twitter, Facebook and LinkedIn. Your mileage WILL vary. So, take everything with a grain of salt and consider the source. However, for some ideas you want to vet and sanity check The Socials can be a great way to Challenge Your Thinking.

Nota Bene: Validate anything you find. Like everything there are no guarantees that the information you find is vetted for accuracy. This includes your original thinking too.

Why do any of this?

In some cases it’s a thought experiment. Just to prove out your thinking and to allow someone else to poke holes in your ideas. Other times you really want to sanity check an idea. Having a group of friends — no matter where they happen to be in the world — is a great way to Challenge Your Thinking.

Sometimes these CYT sessions can turn into collaborative projects where you might want to pool your resources to create something. Other times you may discover that your idea needs some work. And, of course, as you find your groove and you get your trusted advisors on board to regularly Challenge Your Thinking you may just launch the next great product that takes the market by storm.

It’s a two way street. Don’t always assume people want you to be their Brutally Candid and CYT sound board. But, make the offer.

As you get better at Challenge Your Thinking scenarios you will likely find your skills to be in demand and that your truly Stand Out in Your Career.

Who is Challenging your Thinking?

What are your best examples of Challenge Thinking?