How to Have Deeper and More Meaningful Conversations

with guest Jordan Harbinger #MakingBank S6E5

Sometimes breaking the ice with new people in your life seems unusually challenging. Everyone has their own interests and areas of expertise, and it can be hard to find common ground or get through jargon you may be unfamiliar with, even when you are genuinely interested. And other times, you feel yourself having the same surface-level conversations with everyone you meet. If you want to go deeper and start to have more interesting conversations, take notes from Jordan Harbinger.  

Jordan is a Wall Street lawyer turned podcast interviewer known for his approachable style and his knack for frequently securing high profile guests. The Jordan Harbinger Show was selected as one of Apple’s Best in 2018, and today the show sees over 11 million downloads every month. Jordan speaks five languages and has worked for various governments and NGOs overseas, traveling through warzones, and even getting kidnapped (twice). Jordan says his ability to talk his way out of, or into, any situation is the only reason he’s alive today. 

During his interview on the Making Bank podcast, Jordan shares his experience learning the importance of having deeper and more personal, insightful conversations, both on his podcast and in his everyday life. He draws on his years of expertise from teaching networking skills, and how to use those interpersonal social skills in order to have better conversations. 

Do Your Homework 

Whether you’re meeting someone new in your personal life or trying to charm a new client or supplier, knowing a little background is vital. Research, research, research. Find out what this person specializes in. Have they written books, have they published their work in professional journals? Is there a certain belief or idea they’re known for? Get to know as much about them on your own as you can, and spend twice as much time doing so as you think you should. 

Jordan believes this level of preparation is so important because it allows him to be a more active participant in a conversation that could otherwise be out of his comfort zone. Jordan estimates he spends 10-15 hours researching and preparing for every conversation with every guest he invites onto The Jordan Harbinger Show. That way, rather than passively listening to a guest share their knowledge and saying, “Wow, that’s so inspiring,” he’s able to ask informed questions, unpack complex ideas, and engage the guest more deeply in their respective specializations. 

Meet People Where They’re At 

Even with tons of research and prep at your disposal, it’s important to still let the expert drive their own conversation. The point of having background knowledge of your own is so you’re able to rephrase their jargon and expertise into layman’s terms and analogies, which frees up your conversation partner from feeling like they need to “dumb down” anything they say. By signaling that you’re familiar with their work and have a base knowledge of their particular field, they’ll realize that they can get more specific and dive deeper into the subject.  

Jordan talks about the importance of signaling that you’ve done some preparation of your own during his interview with Josh. Sometimes, he explains, experts will have got into a habit of sharing their same “soundbites” during every interview. However, when their conversation partner can say, “Well, that part of your book said something else,” or “What did you think about that article last month on this topic,” that expert will have to divert from their usual “script” or soundbites to have a more organic, in-depth conversation. 

Make Networking Interesting 

Jordan shares how his podcast has evolved over the years, but in the beginning he focused on teaching skills, especially networking. He now has a free online course on networking, but The Jordan Harbinger Show has moved away from teaching skills and focuses more on sharing a variety of vibrant, engaging, and insightful stories from interesting people all over the world. And yet, in a way, this is still networking.  

Bringing more intention and preparation into the way you have conversations will only benefit your networking skills. Knowing how to tap into someone’s interests and experiences, and being able to keep up when they get technical or specific, is what helps to create a memorable, unique interaction in someone’s mind. In a networking environment, you can meet dozens and dozens of people at a time. You’re going to best remember the people that made you feel heard and showed genuine interest and engagement in what you had to say.  

So, don’t be afraid to guide your conversations deeper and away from the surface level. Signal that you’ve done your own research, ask questions that reinforce your base knowledge, practice active listening by rephrasing key points back to them, and you’ll open the door to more interesting discussions.