One lesson I’ve learned that I’ve used throughout my career and in life is the importance of how you open a conversation. It’s such a simple thing, but the key is not starting out with a yes/no question. A yes/no question puts your back up against the wall.

In order to make the most out of a conversation — doesn’t matter if it’s a sales meeting or a talking with a friend — give someone room to answer.

Here’s an example that I hear all the time.

“You doing okay tonight?”


Oh geez, what now? Where do you even begin this conversation now? You’re already backed into a corner that’s going to be hard to get out of.

A better approach looks like this.

“By the way, I’m Ralph Barsi. This is how I learned about this event. I didn’t even know about it until two days ago, but here I am. How did you find out about it?”

That’s an open-ended question, one that’s going to encourage a person to have a conversation with you. You’re going to get a longer answer and you’re going to get a lot more engaged answer, rather than an awkward one-word response.

If you’re headed to an event, it helps to have a goal in mind. What do you want to accomplish? Are there four people that you really want to meet? What have you done to prepare to just kind of run into them over there at the bar? What are you going to say to them? Besides open-ended questions, the other key to starting successful conversations is doing your homework.

The same applies when you’re about to call someone on the phone. If I’m going to call Sean Sheppard, you can bet I’m going to be looking him up. He’s got it all out there. You could learn all about Sean, and there’s 50 different things I could talk to Sean about. I could talk to him about golf, I could talk to him about seed funds, I could talk to him about startups, I could talk to him about GrowthX or cohorts, I could talk to him about B2B sales.

It’s not hard to get some information on someone in advance. A minute or two of advance work can clue you in on whatever they’re interested in.

If you come in with a game-plan, and start off your conversation with an open-ended question, you’re setting yourself up to succeed.

When you’re meeting someone, it could be a good 12 to 18 months before a particular person is  going to give you the time of day again. Earn the right by doing the homework and preparing to have very good conversation flow. Do not get in front of them going eight miles per hour slower than they are.