How winners handle any difficult conversation with a simple psychology hack

You know the feeling.

That one conversation. The one you keep putting off. The one that you should just “get it over with.”

But, no matter how many great articles you’ve read online or how many communication courses you’ve taken, it doesn’t get easier.

You probably know someone, who’s like a “conversational-ninja.” People who effortlessly handle every difficult conversation like it was nothing.

What’s their secret? What do they know that you don’t?

Let me give you an example:

Let’s say you wanted to lose weight. What could you do?

You could:

  • Do a Google search and look up the first and best “diet-plan” (get ready to go through over 30 million results)
  • Buy a weight loss book on Amazon
  • Hire a personal trainer

All those things are just tactics. And tactics are not the real problem.

The truth is, we’ve never had more knowledge about how to lose weight than we do now. So then, why is obesity a bigger problem than ever?

The secret to weight loss and how to handle difficult conversations is exactly the same.

It’s all about controlling your psychology. You can worry about the tactics later.

Now, I’m not saying tactics aren’t important because they are. But those tactics are useless if you don’t handle your psychology first.

Today, I’ll show you how to overcome any difficult conversation by controlling your psychology. I’ll also give you some specific tactics you can use.

Let’s dive in!


Let me give you a few examples of why psychology always comes first in difficult conversations.

See if you can spot something similar in these three examples:

  • The difficult conversation with your husband or wife about some issue that’s been nagging in the back of your head for way too long
  • The difficult conversation with your business partner where you have to figure out whether or not you both want to do the same thing
  • The difficult conversations with your kids after they’ve disappointed you in one way or another

Notice some similarities?

The most difficult thing in those examples is not figuring out what specific words to say… it’s not about finding the perfect time and place… 90% of the time the #1 thing holding you back from taking action in any difficult conversation is your own emotions.

Question is:

If the real problem is handling your own emotions, how do you consciously control them?

You do what’s called a “reframe.”

IBM has the perfect example of how to reframe a problem:

IBM lost $10 million because of a decision made by one of its VP’s. He was called to the office to speak to IBM’s CEO, at the time, Tom Watson Jr.

The VP was sure he was about to be fired, so he had already prepared his resignation letter. Tom Watson Jr. shook his head:

“Are you crazy? You’re not leaving us after we just gave you a $10 million education.”

Essentially, Tom Watson Jr. had two choices:

  1. He could focus on the $10,000,000 loss, or…
  2. Turn the problem upside down

Here’s what I mean:

Of course, losing $10 million is not something you plan for. The real lesson here is, that in ANY situation, you can always decide to look for the silver lining.

The situation is what it is. But, you can ALWAYS change the meaning you give it.

And the way you do it is by asking yourself some great questions.

Obviously, the questions you ask depends on the situation, and the type of difficult conversation you need to handle. But, in general, there are some questions that will work 90% of the time.

For example:

  • “What else could this mean?”
  • “What’s the one thing I can learn from this?”
  • “What is it I don’t understand or see right now?”

So, you control the emotional part of the conversation, by asking yourself some great questions beforehand. This is, by far, the most important aspect.

That’s the psychological aspect.

Let’s look at how you make sure that your next difficult conversation goes as smoothly as possible.


When people prepare for a difficult conversation, one of two things usually happen:

  1. They don’t prepare enough. They “wing it,” and hope their experience is enough to handle it
  2. They prepare way, WAY too much

Human beings are cognitive misers. This means, our brain always tries to find “the path of least resistance.”

Basically, we don’t want to do too much work, if we don’t have to. Our brain just can’t handle too much information at once (sorry to all of you self-proclaimed “multitaskers”).

In a difficult conversation, you really only need to do one thing:

You focus on ONE thing.

Here’s what I mean.

Let’s say you need to deal with a difficult conversation with an employee, your spouse, or your children. Here’s the best way to do it:

  • Focus on one main thing: This means ONLY one thing. This seems obvious, but, you’d be amazed how many people gloss over this part
  • Focus on one main outcome of the conversation. Ask yourself: “What’s the #1 thing I want my employee/manager/spouse/child to understand?”

Don’t give them vague generalities like, “just do better next time.” Instead, give them one specific, tangible, and actionable thing they can do.

Make it dead-simple for people to have success. Life is hard enough already.

Next, let’s look at how you’ll always be prepared for any difficult conversation in the future.


Let’s be real.

No matter what the situation, 80% of the hard work, always happens upfront.

For example:

  • Negotiation: The hard work happens before you ever sit at the negotiating table (i.e. building your network, research, preparing your resume)
  • Fitness: The hard work happens outside the gym (i.e. your diet, your sleep, your stress levels)
  • Sales: The hard work happens before you ever pick up the phone and call your first prospect (i.e. sales training, research, refining your pitch)

The same is true with difficult conversations. You do the hard work upfront.

Luckily, this is everything you need to know:

  • Ask a bad question, get a bad answer
  • Ask a great question, get a great answer

So, it would make sense to have some great questions ready before you need them. The solution is to prepare your questions upfront. I call this your “Questions Vault.”

This is how you use it:

You test different questions. You see the kind of response you get. And you save the best ones in your Questions Vault.

It can be something as simple as an Evernote file, that’s what I do. Take a look at my Questions Vault:

At this point, you need to control the temptation to make things fancy. Focus on making it simple, easy to remember and quick to get a hold of.

Here are a few questions you can use in your Questions Vault. They work in any difficult conversation:

  • “What’s your opinion about X?”
  • “What your biggest challenge right now?”
  • “How can I help?”
  • “What have you tried so far?”


Any difficult conversation can be boiled down this:

Control your own emotions by reframing the problem to make the conversation 10x easier.

Look at the problem from different angles. Show the other person you actually care about how they feel. Ask yourself some great questions to get your emotions under control.

It doesn’t need to be more difficult than it already is to handle difficult conversations.

Test out your different questions from your Questions Vault, and see how the situation changes. You’ll be surprised how a subtle shift in focus can change everything.

Here’s my challenge to you:

I challenge you to test your questions out today!

No more procrastinating. No more excuses. No more B.S. The real difference between average performers and true top performers is one thing:

They always take action as fast as possible.

Test out some different questions and let me know how it goes in the comments. I would love to hear about your success.

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