How to Have More Engaging Conversations

How to Have More Engaging Conversations — with Jordan Harbinger

If you want to have to have epic conversations with anyone — and learn the best conversation starters — Jordan Harbinger is your man.

Jordan is the co-founder of the top 50 iTunes podcast Art of Charm… a show that 4 million people listen to each month. 🔊

Art of Charm features amazing stories from impressive guests like Shaq, Tony Hawk... and Noah Kagan, DUH. 😃

In total, Jordan has interviewed over 1,000 different entrepreneurs, celebrities, and world-class performers.

If you’re looking to improve your conversation skills in business and life, you’ll love this podcast episode.

3 key things you’ll learn:

  1. How to avoid awkward conversations — and impress anyone you meet
  2. The biggest conversation mistakes 99% of people make
  3. Our FAVORITE questions to ask people (which lead to amazing stories)

1. How to have better conversations

After starting Noah Kagan Presents, I’ve interviewed some incredible people who are world-class at what they do.

But making a podcast isn’t easy.

Behind-the-scenes, it can be hard:

  • How do I bring out the best stories in people?
  • What are deep conversation starters to get the conversation flowing?
  • Which fun conversation starters will keep the other person engaged?

One of the biggest mistakes I could make is forcing prepared questions. If I go into an interview feeling super rigid, I won’t let the fun stuff flow.

These lessons aren’t just about podcasts either…

In a job interview, if you practice too much you sound robotic and weird. 🤖

During a date, if you’re constantly bombarding the other person with pre-prepared questions you’re definitely not getting lucky. 😞

If you over-prepare for a customer call, and you know everything about your client, you sound creepy. 👎

The key to good conversation is preparation + curiosity.

Prepare questions to help you push past any awkward situations — but make sure they’re focused on curiosity.

What REALLY excites you about the person, job, or business?

Curiosity is the simplest way to get great stories.

For example, when I asked Jesse Itzler what inspires him he told me about his “life resume” and trying new things is his motivation.

I asked this question because I was genuinely curious what inspires a dude like Jesse to invite a Navy SEAL to live with him for 31 days.

In other words, I was willing to sacrifice non-related questions because my first question inspired a great story.

Next time you’re talking with a potential customer, at a party, or on a date, embrace curiosity with your conversation starters.

2. How to find great conversation starters and ask great questions

There are multiple ways you can ask questions. Funny conversation starters, deep conversation starters… there are tons of choices.

But most of the time, people totally screw it up.

Most people get lazy and ask boring questions that lead to boring answers. 😴

For example, I get asked all the time why I started Sumo.

I’ve said the same responses thousands of times, and now I don’t even think about it:

  • “I got fired from Facebook and wanted to start my own company”
  • “I wanted freedom to do my own thing and work from anywhere”
  • “I enjoy marketing and wanted to make software to help other marketers”

Honestly, if you ask me questions like this, it’s boring for you too!

You’ve heard answers like this before. They’re generic. You don’t learn anything you couldn’t Google.

But with a simple tweak (thanks to Jordan), you can get MUCH more interesting answers…

Use “how” to ask open-ended questions which lead to ultra-engaging stories.

For example, asking me, “how did you come to the idea of starting Sumo?” would deliver a far more engaging story than ,“why did you start Sumo?”

I tried this recently when I met up with Daniel Schreiber (who recently started a tech company) with a question about how he decided to start a company after law school.

The story he shared was more interesting than if I’d just asked: “Why did you start Lemonade?”

Some other fun conversation starters:

  • What’s a recent challenge you had with [X]?
  • [X] seems to be a trend right now. What do you make of that?
  • What moment inspired you to do [X]?

These kind of questions open up the floor and give the person you’re talking with the chance to respond in an interesting way.

Next time you’re talking with someone new, think about how you can open up your questions in order to get better answers.

3. How to prep for conversations, meetings, and interviews

Did you know Shaq is a trained law enforcement officer?

During a recent interview, Jordan was able to find sides of Shaq we’ve never seen.

Conversation starters with Jordan Harbinger and Shaq

That’s no small feat when you consider that Shaq has been in the public eye for more than 20 years (and been interviewed thousands of times).

So what makes Jordan stand out from other interviewers?

It’s all in the prep work.

When it comes to preparing for interviews, Jordan goes to the next level.

Jordan spends at least 10 hours researching and preparing for every interview he does.

This means:

  • Reading and watching other interviews
  • Searching online for any press coverage and stories
  • Reading books (or listening on Audible)

Remember, the goal isn’t to be overly-rehearsed. It’s not to sound robotic. It’s not to sound boring.

The point of preparing is to find questions other people haven’t asked before — and have a backup plan in case you get stuck.

For example, when Jordan interviewed Tony Hawk, he researched the early skateboarding days. He realized that when Tony started skateboarding, no one cared about skating.

Jordan asked: “How did you decide to keep skating even though nobody cared about it?”

This set Tony off into a bunch of cool stories about his experiences of skating in the 1980s and 90s when no one was watching.

These stories would never have been uncovered if it wasn’t for Jordan’s research and curiosity.

Next time you have a big interview, date, or sales opportunity, ask yourself:

  • What conversation starters will get the person to share?
  • How can I prepare… but not overly prepare?
  • What questions has that person not been asked before?

Listen below for my full conversation with Jordan, including:

  1. More lessons from interviewing 1,000+ famous people (like Shaq and Tony Hawk)
  2. How to have engaging conversations with anyone
  3. Conversation starters — and how to avoid awkward conversations in business and life

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2 responses to “How to Have More Engaging Conversations — with Jordan Harbinger”

Joel Widmer
October 21, 2017 at 9:47 am

Insanely entertaining and helpful interview packed with actionable takeaways! Loved the podcast interview questions and have already started using them. Jordan's examples were interesting too. Made me want to hear the unedited interview!

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Daniel
October 17, 2017 at 1:09 pm

These are all great points. The "how" one is particularly interesting - although I would love to see an interview with Simon Sinek where someone only asked him "How?" instead of "Why?"

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