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.
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.
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 comment he left on a post of mine, he essentially said “I’m not sure I agree with that, and here’s why…“, which led to some great discussion.
Like Todd, I am 100% convinced that Evan does this for the purpose of pushing the conversation forward to help us all learn, and not just to be contrarian.
By asking questions that are both tough and fair, these guys make every conversation that they’re a part of better for everyone involved.