The best people ask the toughest questions

I’ve talked a good bit over the last few weeks about learning to ask better questions, and I’ve seen two people in particular that consistently do a fantastic job of it.

Todd

I was on a “book club” call with Todd Stanton a few weeks ago, and we were very fortunate to have the author of the book on the call with us. As the author was explaining an idea from the book, Todd said “ I agree with your previous point, but not this one. Why do you believe that angle to be true? “.

He wasn’t being rude or pedantic — it was a fantastic question that caused all of us to stop and think and it led to some great conversation.

Evan

The other that comes to mind is Evan Chasteen, who replies to many of my LinkedIn posts (and many other posts too) with questions that cause me to re-think my premise. It’s fantastic.

With many people on LinkedIn, when I view their activity I quickly filter to just “posts”, because their comments are generally just short praises (“Congratulations!” or “Great post!”). Those aren’t bad, as giving praise is a great thing, but as a third-party to the conversation it doesn’t do much for me.

Evan doesn’t comment like that, so I often just search to see what he’s saying on other random posts. In one recent…