Make Room For Questions

My grandmother called it "the gift of gab." More recently people have termed it, "being conversational." Whatever you call it, the art of small talk is a valuable skill to have when your world requires you to thrive in frequently changing settings.

In my career, I've been fortunate to find myself in many new and diverse circumstances, which fuels my soul-level need for variety and discovery. The frequent newness was in part because of my life circumstances when building companies - single with no kids when my business partners were all married with young children. "We have an amazing opportunity, but it's in Hong Kong next week. Send Andy, he'll make it work."

But the other reason was the result of the roles I've played in various organizations, particularly in the sales and partnership side of the house. When you're on the front lines of an organization, success hinges on your ability to walk into a new room and walk out with something of value. But that kind of success isn't only available for people whose careers depend on it. It is something I think we all should practice a little more.

To get better at "the gift of gab" you have to know how to both lead and follow the verbal dance. There is a give and take that you can observe when watching every great conversationalist that I believe breaks down into two parts: Purposeful Questions and Generous Answers.

Purposeful Question:

One of the best first impressions you can make is not with what you know but with what you ask.  Voltaire said, “Judge a man by his questions rather than by his answers.”

Anyone can make a statement that shows an understanding of a subject or a situation, but there real next level conversationalist can ask a question that does this AND expands the value of the conversation for all those involved. When getting to know someone, ask questions that give them as much space as possible to answer how they choose to, but also for you to have something to build on.

Are you originally from this area?

What keeps you busy these days?  

What about that is most exciting to you?

These are three questions that I use for when I am speaking to someone I don't know well, but want to find out if there is something more to our interaction that I haven't discovered yet.

Generous Answers:

If the conversation ever turns to you, you can be a team player and generous even when speaking about yourself. So many times people's responses seem to be crafted simply to satisfy the answer to the question.

Them: So what's your story?

Me:   I'm an executive coach in NYC.

The next level way to do this is to fill you answer with loose and easy to grasp threads that the other person can pull on to continue the conversation.

Them: So what's your story?

Me: I grew up in Texas and learned pretty early on I was good at selling. I've sold life insurance, private jets, and startups.

In the second example I gave the other person at least 5 different threads they could pull on. I gave them five different ways they could choose to take the conversation if they chose to be curious. They could grab onto Texas, selling, insurance, jets, or startups. And if they were a next level conversationalist, they could ask about what I omitted: my family, where I live, or what I do now.

Both of these ideas, Purposeful Questions and Generous Answers are things that don't feel natural when you first start to focus on them, but thankfully they are something you can practice almost daily. The more you bring an awareness to how the conversation is going, how you are showing up as a conversational partner, and the value you are creating in the process, the less painful small talk will be.

What is your favorite question to ask when getting to know someone?  

Quote I'm Thinking A Lot About

“Be regular and orderly in your life so that you may be violent and original in your work.”​ — Gustave Flaubert

Book I Haven't Even Finished But Know I Will Reread This Year

This might be the quickest book to make it into my top 10 books for life ever. I haven't even finished it, but it is so good, I am already telling everyone I know, and now you, that they must read it. (Get it here)

It is the most snackable book I've seen in a long time, there are no chapter numbers, just text until the point is made.

There are no connected philosophies or big throughline concepts that you have to hold in your head and build on, just wisdom from lived experiences shared with examples that resonate.

There is not a good way to summarizethe book except to say that I've never underlined a book more. It is exactly what Rick Rubin said to Andersen Cooper,

"I know what I like and what I don't like. I am decisive about what I like and what I don't like. The have confidence in my taste and my ability to express what I feel has proven helpful for artists."

Yeah, you know, artists like Johnny Cash, Linkin Park, Jay-Z, and Adele to name a few.

Question That Got Me Kicked Out Of Walmart's Tech HQ

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