The real reason why people do shocking things, as told by Chris Voss, how to be a great leader, and 3 ways to have difficult conversations.


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Por and Thalia Toha: Entrepreneur Magazine author | CEO descoberto pelo Player FM e nossa comunidade - Os direitos autorais são de propriedade do editor, não do Player FM, e o áudio é transmitido diretamente de seus servidores. Toque no botão Assinar para acompanhar as atualizações no Player FM, ou copie a feed URL em outros aplicativos de podcast.

If you’ve known me for a long time, you know that I used to be super shy, quiet, and would avoid conversations that I know I needed to have.

I don’t know where this came from. It might’ve been the playground insults that happened whenever I tried to raise my hand and said something. Yeah, I was that little Asian kid who just stayed out of trouble most times.

In some ways this followed me to this day.

And it just made difficult conversations all the more difficult for me. You know, the ones you know you needed to have with your boss, your colleagues, your friends, family, or even your clients and employees.

And it wasn’t until I was well into my professional life do I truly realize what I’ve been missing out.

Turns out, difficult conversations are a wealth of opportunities, not obstacles.

It’s about being all ears and in turn discovering something that supports other people, which then somehow fills you up with relief or even gladness.

This opportunity of discovery comes in many shapes. But from what I can see, there are at least 3 types of difficult conversations that we need to know (and have), to create the massive impact that we wanted to make.


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  1. Bearing bad news to someone you respect.

Ever been SO terrified of breaking bad news to someone you respect that you avoid them for as long as you can?

Years ago when I used to work in corporate America, I used to do this whenever something went sideways. Particularly if I had to share it with someone I admire, respect, or even fear. This often happens if a boss or anyone who has a high stake in you is watching.

It’s mortifying.

But here’s the weird part about it. Delaying the difficult conversation will make it WORSE. SO much worse. The few times I’ve put off sharing bad news, I regretted it.

Whenever there’s bad news that you have to share, share it as soon as possible.

  1. Being upfront with a peer.

You know, sometimes telling someone the truth is not always that simple.

In the past, I was surprised to find that someone who was quite close to me, would just refuse to tell me their thoughts. And I had to hear from other people MONTHS after I first learned that they had been talking behind my back.

And it could very well be that they never did confront the matter because they were afraid that I would look at them differently.

If you’ve ever felt this way about something or someone, there is this concept of Black Swan. The Black Swan is essentially a deep seated motivator and reason behind people’s actions—which former FBI Chris Voss talks about in his book.

I dived into this concept some more in this week’s podcast.

If you have to face difficult conversations with a peer or colleague, discovering their hidden motivator, which they themselves might not even know, is a HUGE service not just to them, but also to you.

And NOT trying to discover it, is actually a disservice to your relationship.

  1. Being all ears for the people around you.

It goes without saying that listening is something we all need to do more.

But what most people don’t talk about, is that sometimes, all there is left to do, is simply to listen, and NOT talk.

Particularly if you have people under your wings whom you’re in charge of. Sometimes the best way to support them is to be all ears.

I saw this happen right before my eyes recently when I went on an excursion with a guide. I had the BEST time ever. Hannah wasn’t only great at sharing her knowledge, she was also highly in tune with how everyone is feeling. She didn’t bulldoze everyone with her agenda.

She listened.

We felt safe.

And I gave her a big fat tip as a way to thank her for something only few people cared to do.

The secret, as it turns out, to success, has less to do with the hustle bravado mentality that’s being paraded out there. It’s more to do with who cares enough to raise their hands and have conversations that needed to happen.

This is true in business, and in life as well.

Tell me, what other types of difficult conversations out there should I add to this list?




In this episode, you will take home:

  • The three different types of conversations every successful people know to have.
  • The people you will need to support to have these conversations. And,
  • Ways to have these challenging conversations.

Here are the show notes to help you listen and get the most out of this episode:

  • 3:43 Why difficult conversations are a place of opportunity to be impactful.
  • 4:25 The skill that few have developed that are actually critical.
  • 5:03 The source of some of my biggest professional milestones.
  • 6:00 The part of the morning that most adults fear, that you didn’t know you also have.
  • 6:45 What Tim Ferris, New York Times best-selling author, said about successful people.
  • 7:45 Why you should have difficult conversations sooner rather than later.
  • 8:06 The time I connected with someone I haven’t connected with a long time.
  • 9:15 The real difference between having challenging conversations earlier rather than later.
  • 10:29 The time that I messed up royally and I didn’t want to have a conversation that I should have.
  • 12:02 What your mentors, boss, people you respect, would’ve done if you have difficult conversations with them sooner rather than later.
  • 12:25 The secret to having a difficult conversation with someone you respect.
  • 14:35 Why having difficult conversations with your peers or colleague is important.
  • 16:34 The time I was on the receiving end of a difficult conversation that should’ve (but never did) happen.
  • 19:09 What hostage negotiator for FBI and author of Never Split the Difference, Chris Voss said every person HAS to know before you walk into any difficult conversation.
  • 20:16 The real reason why someone does things that you never expect or that you don’t understand.
  • 23:09 What we tend to do in difficult conversations that we should avoid.
  • 24:44 The conversation you shouldn’t overlook if you have employees, clients, or people looking up to you.
  • 25:35 How to balance your work life, and taking care of people in your charge.
  • 26:30 The time I felt so safe that any conflict or conversation is never impossible to bring up.
  • 27:57 The type of environment you should create for people in your charge if you want to be great at what you do.
  • 30:25 The one common thread across all difficult conversations, that you should not ignore if you want successful conversations.


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