The New Skill We All Need to Build Better Connections

Have you ever befriended someone and felt a wave of awkwardness when a compliment was exchanged?

Not because it was fake or insincere, but because it left both of you confused. You brush it off. They shrug it away. And the gift of compliment that was supposed to deepen the connection feels...hollow.

I’ve done that—a lot.

And I’ve accidentally roughened and even sabotaged some connections by giving compliments that didn’t land. You’ve probably done it too.

This happened to me twice recently.

The first was with a friend I deeply admire—someone who’s accomplished so much that being around him made me feel inspired. One night, as we talked about his entrepreneurial journey, he shared a perspective that left me speechless. The only response I could muster was:

“Wow, you’re very smart and wise, it's crazy”

To my surprise, he waved it off: “I’m not smart; I’m dumb.” An awkwardness ensued, and I couldn’t figure out why.

The second was on a date.

She showered me with compliments: “You’re so funny and smart.” Instead of feeling flattered, I felt a surge of doubt. What did I say that made her think that? The praise felt vague, unearned, and out of place.

Later that evening, as the conversation fizzled out, she told me we were incompatible. Her compliments earlier? They didn’t feel genuine anymore.

Both moments made me realize something: many compliments I give and have received are judgments, not connections. Without context or specificity, they can feel empty, awkward, or even manipulative.

It may sound stingy to fret over a compliment—and it’s not about obsessing over every word you say or others say. There are times when it’s okay to keep things simple, especially with close friends.

But small moments like this compound over time. They’re worth reflecting on because our words, however small, shape how others perceive us.

The world is craving connection more than ever, yet we’re becoming more isolated by the day.

We live in an age of infinite information and fleeting interactions. Social media has replaced in-person connection for many, leaving people hungry for depth.

Work-from-home culture and the speed of modern life have turned relationships into surface-level exchanges. Third spaces are deteriorating and people are more desperate for connection than ever.

In a world where loneliness is on the rise, mastering meaningful communication isn’t just a nice skill to have—it’s essential.

You and I both crave it: a connection that feels real, human, and grounding. But here’s the truth: it won’t happen on its own. We need to take it upon ourselves to become the facilitators of this connection.

When we communicate, what we say is often a fraction of what we mean. Think of it as trying to capture an entire landscape with a single photograph—your words—to get part of the picture but not the full scene. Similarly, the words in our minds rarely translate perfectly to the ears of others.

This gap between intention and interpretation is one of the biggest barriers to connection.

Compliments, in particular, suffer from this misalignment. A vague “You’re so smart” might feel genuine to the speaker but leave the listener wondering, What does that even mean?

To bridge this gap, we need to become more intentional with our language. By grounding our praise in specifics—connecting it to someone’s actions or traits—we can create compliments that feel meaningful, authentic, and grateful for the other person.

Why Conventional Compliments Feel Inauthentic

What does it mean to be judged?

“You’re ugly. You’re stupid. You're lazy”

Most of us understand how harmful negative judgment can be. But as the duality of the universe, judgment also exists in the positive:

“You’re so beautiful. You’re so smart. You did great.”

On the surface, these seem harmless—even kind—but they carry the same weight of expectation.

When we judge others, even positively, we impose our perception of “right” and “wrong” onto them.

Vertical Relationship of Praises

A good way to understand judgment is through the lens of Adlerian psychology in The Courage to Be Disliked. It warns against both praise and rebuke, arguing that they create a vertical relationship—where one person places themselves above the other as an authority.

Think of the classic “Good job!” from a parent, teacher, or boss after a chore or assignment. It might seem encouraging, but it’s a subtle assertion of authority. It's positive reinforcement to keep you going at what they want from you (their idea of the best career, max productivity for the company).

The person giving the praise becomes the judge, and their approval becomes something we crave. This dynamic often leads to resentment because nobody wants to live under someone else’s expectations—not even well-intentioned ones.

We want to act because we choose to—not because someone else projects their desires onto us or manipulated us.

For reference, praising is one of the tools explained by Robert Greene's The 48 Laws of Power to manipulate people.

Flattery creates the illusion of trust while subtly positioning the giver to extract something from you.

We’ve all met someone who over-compliments—“You’re amazing! You’re the best!”—and instinctively felt their insincerity. Their words aren’t about seeing you; they’re about taking from you.

This is why conventional compliments often feel hollow or even uncomfortable. We don’t want to be judged—positively or negatively.

What we truly crave is to be valued for who we are—not for what someone else thinks we should be.

I’ve felt this deeply. At one point, I craved validation. I longed for people to tell me I was smart, capable, or worthy. But what I really needed wasn’t their approval. I needed to feel seen—not judged, not manipulated—just appreciated.

Appreciated, accepted, and loved for everything that makes me me.

My strengths, my flaws, and the impact I’ve had on others. The slightly awkward dumb humor I use to make people laugh. My attempts to connect with others and interest in others. The mistakes I’ve made along the way and learned from.

I wanted to be noticed, accepted, and understood—not for meeting someone else’s expectations, but for all that I am.

People everywhere are dying for this—to feel seen, understood, and valued.

And the simplest way to receive that gift is to start giving it to others first.

Mindful Compliments

The key principle to meaningful compliments isn’t praise—it’s presence.

Gratitude, authenticity, and curiosity are rooted in the present moment and create connection. When you express gratitude, there’s no expectation, no neediness, and no judgment.

You’re not labeling someone based on your past perception of them or hoping for something in return for the future. Instead, you’re simply acknowledging the impact they’ve had on you. It’s not a vertical relationship, it’s a horizontal relationship where both people are on equal standing.

So, how do you do this?

Instead of offering vague praise, shift to mindful acknowledgment. Instead of focusing on the praise, focus on: "How has my life been improved by this person?"

One simple framework, inspired by Non-Violent Communication and shared by Newell of Knowledge, involves three steps:

1. What they did: Identify a specific action that the other person did that made your life easier.

2. Why it mattered: Explain the particular need of yours that was fulfilled.

3. How it made you feel: Share the effects of your emotions honestly.

Specificity is the key to making this framework work.

Here are some examples:

• “When you invited me to hang out last weekend, I felt cared for because I’d been feeling lonely all week.”

• “When you shared your story about your startup journey, I felt affirmed and inspired. I’ve been uncertain about my next steps, and your words gave me affirmation and clarity.”

• “I really love your jacket. The bold colors and unique design make it stand out—I admire your attention to detail.”

When you compliment in this way, notice what happens:

• The pressure lifts. They don’t feel like they have to prove anything to you.

• People have clarity of the impact that you have on them so there is no room for doubt—you're simply stating how you feel.

• The relationship deepens. You’re not passing judgment; you’re simply sharing your experience and an appreciation between yourselves.

This approach shifts compliments from being about them meeting an expectation to being about you appreciating their impact. It’s authentic, grounded, and free of manipulation.

For example: if you’re reading this article right now, I feel grateful and heard. It makes me understood and valued that you took time out of your day to take interest in what I have to say.

Seriously, thank you. And Happy Thanksgiving.

Until next time,

- AL

PS: Checkout my youtube channel, I'll be uploading to YouTube more frequently.