How to encourage someone in 3 steps

Knowing how to encourage someone is key for:

  • Fostering lasting relationships
  • Developing crucial leadership skills
  • Helping struggling loved ones improve their lives.

… BUT if you do it wrong, it’s an easy way to frustrate everyone, or worse, come across as a know-it-all.

I’m not going to let that happen to you though. I want to show you a great system to help you learn how to encourage someone today.

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How to encourage someone

Here’s the secret to encouraging people you won’t hear from 99.9% of life coaches and self-help books:

You can only encourage someone if they want it.

Think back to high school. I’d be willing to bet that the majority of you have forgotten things from your math classes like the quadratic formula or whatever the heck a protractor does. BUT if I asked you all the words to a song you loved in high school — the one you blasted in the car with your friends and every morning on the way to school — you’d be able to sing it to me perfectly (vocal skills depending).

The same idea applies to encouragement; it’s only effective and ingrained in us when we want it. It’s human nature.

So if you try to encourage someone who doesn’t want it you’re just wasting your time.

This might seem callous but it’s actually very freeing. When you’re able to recognize who’s ready to be encouraged, you’ll know where to focus your energy when it comes to helping people who need it.

I’ve developed a three-step system to help you identify these moments to help you encourage anyone willing to improve themselves.

Step 1: Stop and listen

I got this email from a reader a while back:

From: “J.”

Subject: My question is your next blog topic.

My mother is a hot mess. In a sense, I arose from the ashes of poverty while she still hangs her hat there. She came to visit for Thanksgiving and asked me how I “made my millions” (slight exaggeration) so she could too. I don’t know how to tell her she sucks with money and that she needs to get her shit straight before she can dream of island vacations, or even owning a new car on her own.

Thoughts on how to tell a single mom who raised a half a dozen children who’s 60+ years old that she doesn’t know what the hell she’s doing and needs to get her shit in gear?

You’re the man. If you have questions, I’m available on my cell or by email.

All the Best,


Notice what is going on here. This reader wants to encourage his mother — but is being very judgemental. His moral righteousness is preventing him from realizing a key thing: His mother is starting in the same place he did.

He even acknowledges it saying, “I arose from the ashes of poverty while she still hangs her hat there.” But he still goes into a judgemental tirade about how his mother is screwing up.

His first step should have been to step back and acknowledge where she is in the journey. Like him, she also started from poverty. Unlike him, there were probably different potentially bigger barriers in her way, like raising children.

The worst people in the world are people who just learned enough to be dangerous (typically, people who just learned about paleo, weightlifting, or personal finance). They’ve gone through the journey of deciding to change their life, so now they believe everyone needs to join them … without realizing that three months before, they wouldn’t have wanted to hear any of that!

So if someone comes to you who needs encouragement, your first step should always be to stop and listen. Empathize with where they are in their journey.

Two other key points:

  1. Spend time building rapport. It’s easy to launch into how “simple” or “easy” the solution to someone’s problems is. Instead, spend the majority of your time just listening. The conversation should be 90% them 10% you.
  2. Acknowledge their feelings. There’s no better way to discourage someone than by telling them their feelings aren’t legitimate. If someone who needs encouragement comes to you, acknowledge and address their emotions — even if you don’t quite agree with them.
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Step 2: Measure how serious they are

Your next step is to discern if they’re ready to be encouraged.

Say a friend comes to you and is telling you about how he’s really struggling with his credit card debt. He also knows you recently got out of debt yourself.

You’ve listened to him talk, empathized with him, and now you’re going to ask him one simple question:

“How serious are you?”

This is key. If your friend’s answer is anything other than, “I’m very serious. I’m ready to do anything to get out of debt,” they don’t want your encouragement and probably just wanted to just complain or feel validated.

In that case, just smile and say, “You’re doing great. I’m sure you’ll figure things out.” Anything more than that would be a waste of time and energy for you.

However, if they communicate that they’re ready for genuine encouragement, move onto the next step.

Step 3: Give them genuine encouragement

Like giving a good compliment, encouraging someone requires authenticity. That’s why you should avoid giving meaningless platitudes like:

  • “Where there’s a will, there’s a way!”
  • “The universe never gives you more than you can handle!”
  • “What doesn’t kill you makes you stronger!”

In fact, NEVER utter any of the phrases above out loud to anyone. The world will be better for it.

Instead, a genuine encouragement acknowledges their struggles and offers a potential solution to their problems.

Let’s take your friend who’s talking to you about debt. After listening you ask, “How serious are you?”

SCENARIO 1: I want to get out of debt! I’m just awful with numbers and this economy is so lame and—

Stop. They don’t really want to know a great system to get out of debt. They just want to complain and for you to listen to them.

YOUR ANSWER: Yeah, it’s tough. I just make sure I’m paying my bills each month.

Another scenario:

SCENARIO 2: Yeah, I’d really like to get out of debt. I’m trying this new thing where I’m cutting out lattes each month and skipping every other meal.

They’re not looking for technical advice. They just want to feel better about what they’re doing. In this case, validate them.

YOUR ANSWER: Good job. That sounds difficult.

Final scenario:

SCENARIO 3: I’m serious. I’ve been reading a few blogs about budgeting. I’ve been contributing X% of my paycheck towards my debt. How did you do it? You got out of debt so fast last year, I want to know how. I’ll do whatever you did.

Now your friend is ready for helpful, genuine encouragement. They’re showing that they’re ready to accept what you have to say and are eager to hear it.

YOUR ANSWER: Great! It sounds like you’re already doing a great job with the research and paying down your debt. Tell you what, send me an email with the amount of your debt and income and we’ll talk about what else you could be doing to crush your debt.

Notice two things with the last example — these are important:

  • It seems unfathomably rare that anyone would actually say, “I’m serious. I’ll do whatever you tell me to.” Almost nobody ever says this, because almost nobody really wants advice to the level of following through. They want to complain, they want to feel validated, but fewer than 1 in 1,000 actually want to change their behavior. It took me 10 years to truly internalize this. Once you do, you’ll start to be more understanding and empathetic, instead of frustrated.
  • Even though they say they are 100% serious, I still didn’t dive into the deep, technical “how to” because they are not ready. You’re doing them a favor by parceling out your advice — and you’re giving them a minor barrier to see how serious they really are. Anyone can “say” they’re serious. This is an example of using barriers strategically.

Once you offer your advice, close with an authentic compliment for the person you’re talking to. This helps reaffirm to them that they are capable of handling the situation and ends your encouragement on a high note.

Here’s a great example of one:

You: “John, you’re going to do great. You’re one of the most motivated people I know.”

Them: “Why’s that?”

You: “After talking with you, I noticed you genuinely want to get out of your bad situation. Not only that, but you’re actively doing something about it. That’s something I couldn’t say for the majority of people out there.”

Look at how this compliment is authentic and observational. You noticed something about them and responded authentically to it. Not only will this encourage the person you’re talking to, but they’ll appreciate you all the more for it.

In his book “How to Win Friends and Influence People,” Dale Carnegie put it best:

“The difference between appreciation and flattery? That is simple. One is sincere and the other insincere. One comes from the heart out; the other from the teeth out. One is unselfish; the other selfish. One is universally admired; the other universally condemned.”

People aren’t stupid. They know a weak compliment (or “flattery” as Carnegie called it) when they hear it. They also know the value of a good authentic compliment and appreciate it.

Put these elements together and you can encourage anyone who’s ready for it.

Build the skills to encourage anyone

You can give people the best encouragement in the world, hand them the best tactics, techniques, and strategies, but it still won’t work until the pain of staying the same outweighs the pain of putting in the work and making a change.

That means having the intuition to recognize those moments and the confidence to jump right into those social situations.

If you need help getting there, I want to give you something to help.

My team and I have worked on something to help you take your social skills to the next level:

The Ultimate Guide to Social Skills

This is my FREE guide to help you navigate any confusing social situation. You’ll learn how to:

  • Make small talk. I reveal the common mistakes most people make and show you some simple ways to make small talk with anyone.
  • Overcome shyness and build confidence. These are my best strategies on overcoming anxiety and being confident in group settings.
  • Be more likable. Transform yourself into that person who can walk into any bar or party and talk to anyone with ease.

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