Fear No Awkwardness — Chatting is Good

Fear No Awkwardness — Chatting is Good

This post can be considered as part 2 of The Power of One-on-One Meetings and Personal Connections.

Although just a week ago, I wrote The Power of One-on-One Meetings and Personal Connections, I was still hesitant about the one-on-one meetings I had scheduled today. Those amazing feelings from previous one-on-one meetings had left me. I was, once again, skeptical and wondered if these meetings would be any good at all.

The good news is all one-on-one meetings I had today went great! Same as last time, I enjoyed them thoroughly and was glad that I had them.

I want to use this post to not only document and reiterate lessons I learned, but also to serve as a reminder to myself, as I know this won’t be the last time I feel skeptical about one-on-one meetings or, in general, things outside of my comfort zone.

Deep down is the fear of awkwardness.

One of the meetings I had today was with an engineer I never worked with before, so, obviously, it was our first one-on-one meeting. The meeting was scheduled for 30 mins. I worried that we might run out of topics and had to sit in awkwardness, so I thought of a few topics ahead of time.

To provide more context, the goal of the meeting was for us to get to know each other better. To be honest, this goal was where my fear of awkwardness steamed from. Another bit of context is I was, and will continue to be in the next few months, working remotely.

Back to the meeting; it turned out I didn’t need to use my topic list at all. After some small talks, I briefly shared my background before joining Gusto. Then, my colleague started to share his life before Gusto. That 30 mins went by like a breeze as I was so fascinated by his stories.

Before our conversation, all I knew was he was a sharp engineer as I heard many great words about him. I had no idea that he had many spur-of-the-moment adventures, including from not knowing much about poker to being a full-time poker player at Vegas and then accidentally started a successful startup without much technical experience and held onto it for six years. I was blown away by his stories.

Human is multifaceted. We are not just engineers.

In an office setting, it’s easy for us to think of our colleagues as their professions and forget that they are much more profound than that.

It’s only when we look beyond their professions and learn about who they are as a person, we can connect with them at a personal level.

Personal connections are invaluable.

The work-related advantages of having personal connections with colleagues should be self-evident. It not only helps us understand each other better but also makes us look forward to going to work.

What I want to emphasis on non-work-related benefits. Considering we spend a big part of our day, if not life, at work, most of our time are spent working with our colleagues. Don’t you think it would be a bit sad if, after spending all this time together, all we got from each other were things related to work? Our lives might be much enriched and more wonderful if we also learn and get support from our colleagues—the people we spend eight hours a day with.

In my case, I was so inspired by my colleague’s experience that I wanted to learn more about it and had many questions and ideas wanted to share with him.

Sharing ideas and thoughts with someone interesting is one of the most wonderful things. When we stop thinking of our colleagues as their professions and remind ourselves that they are much more than that, we will start to discover fascinating things about them.

Chatting is Good

This kind of discovery happens naturally when you chat casually. I realize I mostly bond with my colleagues during “unproductive” times: when we chat while setting up a pairing station before pair programming or during lunches when we talked about random subjects.

See things from others’ perspective to get a pulse of the team.

Another one-on-one meeting I had was with an engineer I had been working with for a while. This is one of the many one-on-one meetings we had. But this time, I made the meeting an hour long since I noticed our past meetings always ran short.

Since the meeting was much longer, we actually had time to go in-depth into a few topics he brought up. I had more time to listen to my coworker. I saw a fuller picture from his perspective than what I used to get. I was able to better understand how he felt about the project and the team. I recognized some of his concerns resulting from a lack of context and addressed them by providing more information. Without this meeting, I wouldn’t have recognized my coworker had these concerns in the back of his mind and this information which seemed unrelated was actually relevant.

We were also able to cover other topics such as what he wanted to work on next and feedback he had for me.

It was a productive meeting because both of us left with a clearer picture in mind. My coworker had his concerns addressed and also knew what was coming up next. I got a better sense about how he felt and his interests, which would help me make more informed planning decisions.

Overall, I find these one-on-one meetings are great for making sure each person on the team is happy. They help me keep a pulse on the team, which is one of the most important things for leading projects.


My career plan for the year is to grow into a tech lead. I’m excited about all the learnings ahead and would love to share this journey with you in a brutally honest fashion. I will be sharing my weekly learning on the blog.

In the next few months, I will focus on growing in the following areas. You can expect to see posts related to them:

  • focusing on the big picture of the project instead of near-term implementation details;
  • balancing my efforts between leading projects and coding;
  • work-life balance for long-term productivity;
  • the human side of software development: making sure everyone riding with me enjoys the ride and feels fulfilled and inspired.

2 Comments Fear No Awkwardness — Chatting is Good

  1. EDDISON LEWIS

    Yes, whilst the professional relationship at work is critical, eventually, people do connect on a personal level which could lead to overall enrichment to one’s lives………………..

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