How Do I Talk To Coworkers Without Feeling Awkward?

Here is how to make conversations feel natural, confident, and easy, using the simple habits that helped me in my first year out of college.

By
Josh Felgoise

Dec 16, 2025

Mad Men

No one tells you this, but one of the hardest parts of your first job is the small talk. Not the job itself. Not the assignments. Not even the meetings. The really uncomfortable part is standing in the kitchen wondering what to say to the person getting coffee next to you.

Every guy knows that feeling. You want to seem friendly but not awkward. Confident but not forced. Normal but not boring. And somehow that pressure makes everything feel wrong.

When I started my first office job, I felt all of that. But over the past year, I learned a few simple things that make talking to coworkers so much easier. None of this is about pretending to be someone you are not. It is about showing up in a way that makes conversations feel natural instead of stressful.

Here is what actually works.

Start by looking like someone who wants to talk

Before you even speak, your body language answers the question for you.

When I walk into the office, I always take out my AirPods. I said it in the episode because it changed everything for me:

“You truly never know who you’re going to see right when you walk in.”

If your headphones are in, you look closed off. If your eyes are down, you look unavailable. Even if you are friendly, people pick up the opposite signal.

This lines up with what workplace researchers have found about approachability and first impressions. Harvard Business Review has written extensively about how small nonverbal cues shape how coworkers perceive openness and confidence Harvard Business Review on workplace communication.

Sometimes the easiest way to talk to coworkers is to look talkable.

Say hi, even when it feels boring

One of the most important things I learned is that small talk does not have to be interesting. It just has to happen.

In the episode, I said exactly this about the kitchen conversations:

"Just being present and not blocked off.”

That is the whole game. Show up like someone who is willing to say hi and ask a simple question. That is it.

Talking to coworkers becomes awkward when you try too hard.
It becomes normal when you stop overthinking it.

That same overthinking pattern shows up in dating and social situations too, which is why I broke it down in What Jealousy Is Trying To Tell You. Different setting, same mental spiral.

Use the coffee chat mentality (it works everywhere)

If you want to feel less awkward, learn how to ask simple questions that make people open up. Your goal is not to impress them. Your goal is to understand them.

These are the exact questions I mentioned in the episode:

  • What is the best thing about working here

  • What is something you would change

  • What are you working on right now

  • Explain your role to me as if you were explaining it to an old person

That last one always gets a laugh. It breaks the tension. It makes the conversation feel normal.

This is why the coffee chat mentality works.
It gives you a structure when your brain wants to panic.

Have a two minute version of your story ready

When coworkers ask what you do or how you got there, you do not want to freeze. You want a simple, clean version of your story you can say without thinking.

I explained it in the episode like this format:

“I got an internship at X, realized I liked Y, and that led me to apply for this job where I can do more of Z.”

That is all you need.
Short. Confident. Human.

You do not need a perfect story.
You just need something that makes people feel like they understand you.

This is the same principle I talk about when it comes to careers more broadly in How Do I Write a Resume That Actually Works?. Clarity beats complexity every time.

Follow up when it makes sense

If you have a good conversation with someone, send a quick DM or message later.

It does not have to be formal. Something like:

“Great talking today. Loved hearing about what you’re working on.”

I also really think:

“You truly never know what can come from that connection years down the road.”

That is real.
The people you talk to now are the ones who open doors for you later.

Long-term career growth often comes from weak ties, not close friends, something Forbes has covered extensively in articles about networking and opportunity Forbes on networking and career growth.

Know that everyone feels awkward at first

This is the part no one tells you.
Everyone is faking confidence in their first job. Everyone feels unsure. Everyone wonders if they sound weird.

I said something in the episode that every guy needs to hear:

“All the things you have to get done or want to do on top of a nine to five job still stress me out.”

If you’ve ever wondered whether confidence can be learned instead of magically appearing, I went deeper on that in How Do I Act More Confident?

You are not the only one navigating this.
Once you understand that, conversations become easier. The pressure goes away. You show up as yourself.

Ask questions even when you feel dumb

If you want to stop feeling awkward, ask questions.
It sounds simple, but it is the fastest way to gain confidence and build relationships.

I think this is really true:

“Realistically, you start off not knowing anything and the only way you’re going to know something is if you ask.”

Asking questions does not make you look inexperienced.
It makes you look engaged.

People remember the new hire who wants to learn, not the one pretending to know everything.

Be the guy who gets things done

One of the easiest ways to earn respect is to take initiative.
You do not need to make a big announcement.
You do not need credit.
Just be reliable.

You said it best: when something needs to get done and no one is doing it, be the person who steps in.

Coworkers trust people who act, not people who point out problems.
Trust is what makes conversations easier.
Trust is what makes you feel like you belong.

FAQ: What Guys Actually Ask About Talking To Coworkers

What if I run out of things to say?
Ask a question about their role or their weekend. People love talking about themselves more than you think.

What if I feel like they don’t care about talking to me?
Most people are just busy or distracted. Your job is to be open, not to take things personally.

What if I’m naturally quiet?
You do not need to be loud to be friendly. You just need to be present.

How do I avoid sounding awkward?
Stop trying to be impressive. Be curious instead. Curiosity always comes off confident.

How long should small talk last?
Thirty seconds is enough. You are not performing. You are just being a person.