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Pick Someone’s Brain and Hack Inside Information


If you need to pick someone’s brain and hack inside information be smart. Use the “Tell me like I’m stupid” strategy. Here’s how you can get better information and have a better idea what to do with it.

Pick Their Brains

Picking someone’s brain means gathering all the key information that you need to accomplish something. If you are clumsy and rude they will cut you off. If you are smart and focused you walk away with valuable inside information. The way you pick someone’s brain is to ask a lot of smart questions and encourage her to answer in the most complete, understandable way.

Hack Inside Information

The quality of the information you learn is directly dependent on the questions you ask and how well you understand the answers. People who either don’t ask questions or won’t admit they don’t understand constantly amaze me. Years ago I started asking people to make things very simple for me … I mean basic and rudimentary. Since then I get more, better information and have a better idea what to do with it.

Socrates The Sneaky

Socrates was the most famous of the Greek philosophers. Without dipping more than a toe into the pond of history, Socrates seemed to have been a former soldier who somehow managed to avoid work and spend his time discussing philosophy and asking questions. His technique has been called the Socratic Method or in Latin “lascivio stolidus.” That means playing dumb. Socrates would ask extremely simple questions and pretend to not understand so his students kept simplifying and simplifying. It worked really well for Socrates until he screwed up a very important question: “Which cup has the hemlock in it?” Since hemlock is a deadly poison, it wasn’t so smart to play dumb.

Million Dollar Answers – They’re So Easy It’s Stupid

tell-me-like-I'm-stupid If you want to hack inside information from top decision-makers, executives, clients and customers use the “Tell me like I’m stupid” strategy.

Corporate objectives – Tell me like I’m stupid.

Marketing goals – Tell me like I’m stupid.

Content needs – Tell me like I’m stupid.

RFP details – Tell me like I’m stupid.

Project specifications – Tell me like I’m stupid.

Meeting and event plans – Tell me like I’m stupid.

I’ve made the same request of U.S. Senators, CEOs, Chairmen of the Board, Corporate Presidents and a host of directors, managers, clients, ministers and folks at the Genius Bar at the Apple Store. No one was ever offended when I picked their brains.

How To Pick A Brain

There is a big difference between playing dumb and asking people to explain things in the simplest way. That’s what I’m suggesting. So here’s how to ask better questions, hack inside information and get more value from the answers.

Never say, “I want to pick your brain.” It sounds a little too gross and biological. Would you ask to pick their nose? Be smart. Before you ask the first question, you need to do two critical things. Skip these steps and your chances of success are pretty slim.

#1 – Decide what you need to know.

Few people have the time or patience for an aimless fishing expedition. Do some homework, have a clear objective in mind and ask questions to meet it.

#2 – Decide why they should tell you.

Why should that person take the time to answer your questions? Make sure you can provide a compelling motivation. This is the single reason most people don’t walk away with the high-quality information they need. The other person has no reason to give it to them.

Make It Easy To Tell You

It isn’t about you it’s about them and what they know. Unless it’s an investigative report for 60 Minutes you don’t want confrontation. You want cooperation and to make sure they don’t feel like you’ve wasted their time.

The Super Secret On Hacking Inside Information

It is basic human nature. People want to please you. Subconsciously they want to know that they gave you the answer you want and need. So make it easy.

When I ask them to tell me like I’m stupid I explain that I will ask some very simple, basic questions. I’m not really dumb but simple questions make it easier for them to explain in a way that makes sure I understand what they’re telling me.

99% of the time this is met by a laugh, a smile and a sign of relief. Suddenly we’re partners in the questions and the answers. I even ask if there’s a better way to word the question. It’s easy to hack inside information when people just tell you. Now let’s get down to business.

Tell Me Like I’m Stupid Strategy

Ask a specific question to get a specific answer. No trick or vague questions. Don’t expect the other person to guess what you mean, tell them.

Start with something very simple. Listen carefully and follow up on anything that might need additional explanation. Then go on to the next logical question, again very, very simple.

Accept what they tell you at face value. Don’t debate, listen for understanding.

Play back what they told you. When you repeat the key points it proves that you’ve heard them and it saves tons of time.

Stay focused. This isn’t a fishing expedition. Be precise, focused and very respectful of their time.

If You Don’t Understand It’s Your Fault

Tell me like I’m stupid simplifies everything. Instead of trying to decide if you should be asking a probing, leading, funnel, rhetorical, open or closed question – you can focus on understanding the answer. It’s like a trip on the interstate. The direct route is the most efficient but it can be more interesting to take a few side roads. You get to the same destination.

Now you may have a better approach to hack inside information and I’d like to know it. But, please, tell me like I’m stupid.

Let’s spend 15 minutes talking about your next project or challenge. Just click on CONTACT US or send an email to and get in touch.


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About the Author
Andy Johnston is a multi-faceted communication professional who has a comfortable way of working with people. Andy is an Emmy Award winning communicator known for his energy, humor, creativity and his unique ability to discover the key results that must be generated – and then to develop ingenious ways to engage and motivate audiences. He has broad experience in strategic planning, messaging, creative direction, marketing, and events. One of the things Andy says often is, “How can we make it better?”
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