#94: You Know Less About People Than You Think
How to become a Supercommunicator
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Hey Friends,
Welcome to the 93rd edition of my newsletter.
I had a very busy week at work, as on Tuesday, we had our annual Tax&Legal conference, and on Wednesday, I had to fly to Warsaw for a gathering of the regional technology leaders.
Nice experiences. It was lovely to meet some people for the first time in person, but it was also quite tiresome, and I missed Zeno, as it was the first night I was away since he was born.
That’s why I will be quite brief today, and I want to talk about communication.
You Know Less About People Than You Think
We like to think we’re good at reading people.
It’s like that statistic saying that 80% of drivers think they are better than the average.
Well, it turns out we are not the best communicators.
Or at least not yet.
I was reading Charles Duhigg’s Supercommunicators the other day, and it explained that real connection happens when we go beyond surface-level interactions and uncover what’s really driving people.
Too often, we communicate based on assumptions—without realizing that we’re missing critical pieces of the story.
We see a colleague who seems disengaged in meetings, and we assume they don’t care.
We hear a blunt response from a team member and label them as difficult.
We think we know why people act the way they do.
But the truth is, we usually don’t.
And every interaction operates on three levels:
Practical - The facts: What’s being discussed?
Emotional – The feelings: How does this person feel about it?
Social – The relationship: What does this mean for our dynamic?
Most people stay stuck on the practical level, assuming that a problem is just about facts or logic. But more often, the real issue is emotional or social.
Imagine you’re leading a meeting, and a team member keeps pushing back on a new idea. Your instinct might be to assume they’re being difficult or resistant to change.
But what if:
They had a past project fail similarly and are afraid of repeating the mistake.
They feel unheard in decision-making and are asserting their voice.
They’re going through some personal stuff that’s affecting their ability to process change.
You won’t know unless you ask.
How to Truly Connect with People
Get comfortable with not knowing
Instead of assuming, adopt a mindset of curiosity. When someone’s response surprises you, ask yourself: What else might be going on here?
Ask deeper questions
People open up when they feel genuinely seen. Instead of “How’s it going?” try:
“What’s been on your mind lately?”
“What’s something challenging you’ve been dealing with?”
“If you could change one thing about this situation, what would it be?”
Use ‘looping’ to confirm understanding
Before offering advice or solutions, reflect back on what you hear:
“It sounds like you’re frustrated because this change feels rushed—did I get that right?”
This small step makes people feel heard and encourages them to share more.Create a culture where people can be real
If people fear judgment, they’ll only share surface-level thoughts. Make it clear that honesty is valued by saying:“It’s okay to disagree; I want to hear your real concerns.”
“I appreciate you sharing that—I know it’s not always easy to speak up.”
Try This This Week
Next time someone reacts unexpectedly, pause. Instead of assuming, ask: “Hey, I noticed you seemed concerned about this—what’s on your mind?”
Have a deeper conversation. Ask a colleague or team member one non-work-related question that goes beyond small talk.
Notice the levels of conversation. Is a disagreement actually about facts, or is there an emotional or social layer underneath?
The best leaders don’t just communicate well—they uncover the deeper truth behind words, helping others feel truly understood.
Recommendations:
Kindle Scribe.
I’ve had my kindle scribe for a month or so already and I love how the writing feels. I’ve had a Remarkable 2 before and I would say the writing experience is very similar, but I find the Scribe more useful as I can also read on it and it syncs my books and my audiobooks too.
This post about why both ideas and execution matters
This interesting take on AI Agents.
Well, I hope you liked this edition.
Stay Antifragile,
Leo
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