Talk Less, Listen More

In a recent post, I recapped five of my biggest takeaways from side-hustling. I purposely left one lesson off the list because it’s so important that it deserves its own segment.


Growing up we were always told to listen to our teachers, parents, and other authoritative figures. This isn’t the type of listening I’m talking about, and in many cases, I would actually offer the opposite of that advice.

I’m talking about listening to learn and build relationships. People love to talk about themselves, but only when they know there is someone who’s listening. Here are two tips to make you a better listener:

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Ask The Right Questions

An indicator of a good conversation isn’t how many questions you ask, but if you ask the right ones. Often times we fall into a habit of thinking about what to say next, instead of actually listening to what the person is saying. Don’t do this.

Most people listen with the intention of replying, but not understanding. The best conversationalists and networkers are the ones who are able to understand as well as they are able to talk. Curiosity and enthusiasm are contagious. They also make you instantly likable. Asking follow-up questions is a great way to show that you are engaged and interested in what the other person is saying.

Never Rely on Technology

When conducting interviews for my book, I used an app called CallRecordNow to record my conversations. I intended to transcribe the audio later on in the writing process. What I thought to be a helpful productivity hack, was actually a massive crutch. Since I knew I could play back the conversations, I rarely took notes and occasionally let my mind wander. It was only when I lost nearly 60% of my interviews (shoot me a message if you want to hear this story) did I realize how foolish this was. Not only did it hurt me, but also the quality of my discussion. It wasn’t until I realized I was unable to remember main talking points from three separate interviews that I realized how bad of a listener (and notetaker) I really was.

Shell-shocked, I reached out to my friend for advice. He’s the owner of a multimillion dollar travel agency and also happened to be one of the people whose interview had been lost. I told him what happened, begged to speak with him again, and asked if he had any advice for this situation.

His advice: “Always listen :)”

My advice: Always listen, take notes on key ideas, and always hit the damn “merge call” button when you are trying to record a conversation.

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© Randy Ginsburg, 2020 | Want to chat? Email me at