Episode 28: Is That Person the Real Deal?

Judging people in the tech industry is harder than you'd think.

In this world, surface impressions miss the mark all the time.

The person sitting quietly in a rumpled T-shirt might actually be a founder who has built up teams several times over, while the one who commands the room with sharp clothes and a fluent presentation might not understand the first thing about the actual work.

At first, I got it wrong a lot too.

I saw competence in people who spoke well, and a knack for execution in people who answered quickly. I even read a strange sense of reassurance into a confident demeanor. But over time I learned something: the words that put you at ease and the words of someone you can truly trust are two completely different things.

In tech especially, that difference is even more subtle.

Plausible-sounding words are always floating around here.

Innovation, execution, optimization, scalability, agile, pivot, update.

Some people wield these words with great skill. Listen for a moment and they look like someone who has already done half the job. The problem is that, more often than not, those words are just air — they carry no responsibility at all.

“It can be done.”

“That's not hard.”

“We can fix that part in the next version.”

“Let's just go for it.”

These words are fast.

Too fast.

And oddly enough, sometimes being fast alone makes someone look capable. But after you've collided with it a few times, you start to see it: a quick decision and an accurate understanding are not the same thing at all.

Some people reach a conclusion before the other person has even finished speaking. The moment they hear the question, they pull out an answer already prepared in their head. It doesn't matter what context the question came from, what constraints the other person is under, or what they're really worried about. What matters is answering quickly. Showing conviction quickly. And, if possible, seizing control of the conversation.

For a while, I mistook that attitude for skill.

But with time, I realized it was usually closer to a habit than to skill. The habit of speaking before understanding precisely. The habit of being optimistic without being ready to take responsibility. The habit of slipping away, when proven wrong, by saying “the situation changed” or “that's just how startups are.”

From then on, my criteria for reading people slowly began to change.

I came to look at something other than credentials, and to listen for something other than eloquence. And eventually I arrived at a single criterion that has held steady for quite a long time.

Is this someone who listens to me all the way through, and can say it back in their own words?

By now, this criterion has become the most powerful filter I have for deciding whether to trust someone.

The interesting thing is that this criterion doesn't apply to only one side. It holds when judging an applicant, and it holds just as well when judging a company. The employer and the applicant stand in different positions, but in the end they are looking at the same thing.

Does this person really understand?

Can this person stand behind what they've said?

The Employer's View: Why Some Applicants Feel Like a Risk

In the hiring process, many applicants strain to prove themselves.

They cite their achievements, lay out their tech stack, and pitch their problem-solving experience. Those things matter, of course. But when you're actually judging someone you'll work with, a different kind of moment tends to linger longer than you'd expect.

Say you ask a question, and the applicant doesn't listen to it all the way through.

They produce an answer before grasping the context of the question. They focus less on what I want to know than on how smoothly they can slot in the answer they've prepared. These applicants tend to leave a similar impression. They seem well-prepared, yet somehow they make you uneasy. The words are fluent, but you can't quite picture working alongside them.

Why is that?

Because that person reacted to the question rather than understanding it.

A truly good applicant responds differently.

They hear the question and pause for a moment. Then they restate, in their own words, what they understood.

“So the heart of your question isn't really whether I can build this feature, but how I set priorities within uncertain requirements — is that right?”

When you hear an answer like that, you feel it immediately.

Ah — this person isn't just trying to pass the interview; they've grasped exactly what this conversation is for.

From the employer's side, this is the exact moment trust begins.

When an applicant restates the question in their own words, it doesn't simply mean they have good communication skills. It means they know how to structure a situation, that they know how to interpret the other person's intent, and above all that they're unlikely to go charging off in the wrong direction.

From a company's standpoint, the truly dangerous person isn't the one who doesn't know.

It's the one who doesn't listen.

The one who moves fast without understanding.

In real work, information is always incomplete.

Instructions are never perfect, and requirements change often. The more that's true, the more what matters isn't the person who knows a lot of right answers, but the person who can re-extract the essentials even from incomplete inputs.

In the end, employers come to look for that kind of person.

Not the person who knows a lot, but the one who can listen accurately and reconstruct accurately.

The Applicant's View: Why You Shouldn't Join Some Companies

The interesting thing is that this criterion works just as precisely in reverse.

The applicant has to evaluate the company too.

Salary, benefits, title, tech stack — these matter too. But what really matters lies elsewhere.

Is this company trying to understand me properly?

Can this leader explain, in their own words, the work I'll be doing?

Sit through enough interviews and the dangerous companies give themselves away surprisingly fast.

They seem to be listening to the applicant while not actually listening. They've passed judgment before the answer is even finished. Or they describe the role while repeating nothing but abstract words.

“Just take the initiative.”

“Just approach it with ownership.”

“We're a startup, so you'll need to be flexible and do a bit of everything well.”

“Once you're in, there's so much room to grow.”

At first glance, these words sound like possibility.

But listen a little longer and it's unclear who actually owns the responsibility.

What you're supposed to do,

what problem you're supposed to solve,

what the standard for success is,

who makes which decisions.

If a company can't explain these questions clearly in its own words, chances are the structure hasn't been sorted out internally yet either. In the end, that ambiguity becomes the applicant's burden once they join. It easily leads to a position where expectations are high but the role is blurry, where the responsibility is large but the authority is undefined.

A decent employer, by contrast, talks differently.

“What our team needs right now isn't simply someone who's good at development, but someone who can take unclear demands and turn them into a form the team can act on.”

Or they might put it this way.

“The problem we're facing right now isn't a shortage of people; it's that we're losing a lot of context between planning and execution. That's why, for this role, the ability to keep things aligned matters even more than raw productivity.”

When you hear an explanation like that, you feel it.

Ah — this company at least knows what it wants. It understands its own problem at least well enough to be hiring for it.

This, too, is the exact moment an applicant comes to trust a company.

Language that describes its own problem precisely, rather than a dazzling vision. Sentences that lay out roles and responsibilities concretely, rather than abstract enthusiasm. That becomes a far more important signal.

Because what an applicant ultimately joins isn't the company's slogan, but its operating logic.

In the End, Both Sides Are Looking at the Same Thing

On the surface, the employer's question and the applicant's question look different.

The employer asks:

When I hand this applicant a task, will they really understand the context?

The applicant asks:

When this employer hands me a task, will they really explain the context?

But look a little closer, and the two of them are ultimately looking at the same thing.

Does this person really understand?

And when does understanding reveal itself?

I think it always shows up in putting things into your own words — in paraphrasing.

Anyone can repeat someone else's words verbatim. Stringing together fashionable phrases isn't hard either. But to digest what you've heard inside yourself, restructure the essentials, and make the other person respond, “Yes, that's exactly what I wanted to say” — that is an entirely different level of work.

That's the moment trust is born.

When someone can re-explain my words in their own language, it doesn't merely mean they remembered the content. It means they've taken that complex context into their own thinking. It means they've filtered, once, for what is essential, what is peripheral, and where the core of the problem actually lies.

And from that moment on, that person's words are no longer light.

The moment you speak in your own words, what you say stops being someone else's words and becomes your own responsibility.

That's why people who have their own language don't speak carelessly.

Nor do they make easy guarantees.

Instead, they listen precisely, organize carefully, and say only as much as they can stand behind.

I believe that difference ultimately reveals both a person's depth and their attitude at the same time.

Trust, in the End, Reveals Itself in Language

These days, when I size someone up, I look at this moment before their credentials.

After hearing a question,

how they say it back.

After hearing an answer,

how they make sense of it again.

It's the same whether they're the applicant or the employer.

People who don't listen all the way through are generally a risk. People who have no language of their own generally have no responsibility either. People who reach quick certainty without understanding end up pushing the cost onto someone else.

The trustworthy ones, by contrast, are generally alike.

They listen well,

they organize,

and they say it back.

Within that short process, both their thinking and their sense of responsibility come through together.

Good hiring, in the end, is less about finding good credentials than about finding someone who can properly understand what the other person is saying. And a good job move, likewise, isn't only about finding better terms. It's closer to finding someone who can properly understand and explain the problem you'll be taking on.

Applicant and employer alike are, in the end, taking the same test.

Can you listen to the other person all the way through,

and say it back in your own words?

Maybe trust always begins right there.

And am I the real thing? I don't know either.

Only the results will prove it.