The one on one meeting, that awkward recurring time on your calendar to talk with your manager about "whatever you want".

It can be intimidating given the open format and the lack of agenda, but with a few quick tips you can approach one on ones with confidence and maybe even a little excitement.

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My First One on Ones

I didn't have one on ones at my first software engineering job.

I quite liked having almost no meetings and getting to focus on my work and maximizing productivity. Sure, I was able to get a lot done but I wasn't growing and learning as much as I should have been. I felt like a 10x engineer who shipped more code than most of the team but I wasn't becoming a better engineer and I wasn't growing and becoming a more valuable part of the team.

At my second job, the two founders put time on my calendar for one on ones, but I didn't know what to expect.

They said this was my meeting and I was responsible for the agenda. It was on me to bring up any points I wanted to talk about.

Honestly, I would rather skip it and not have to awkwardly talk to my bosses about my feelings. It would take time away from building and shipping a bunch of new features, and I was concerned that they were judging my performance or other soft skills. I was laid off from my previous job too, so I had a constant fear of being suddenly laid off again in almost all of these meetings.

Looking back, I really goofed and didn't take advantage of my one on ones.

The real truth is, one on ones are a massive opportunity for you to explore and get honest feedback that you wouldn't otherwise be able to get.

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Why One on Ones are Wonderful

How great would it be if you had the opportunity to talk one on one and get the undivided attention of someone successful or someone you admire and look up to?

What if you had this opportunity with someone like Elon Musk or Steve Jobs.

Your boss is probably more successful than you and I'd guess has more experience doing what you do. You could probably learn a lot from them to help accelerate your own career. They've been in your shoes. I dreaded one on ones before I understood this, there's a really important mindset that you need to have going into these meetings in order to get the most out of them.

I tried to list a few dumb things to talk about like my weekend plans, and a few questions for the other person to get them talking more to take up time.

Then I flipped a switch. I realized one on ones are not for your boss to judge your performance but for you to have a private conversation with someone who is already where you want to be in a few years. You're getting paid to talk to a mentor.

Its your opportunity to dig into their brain and learn from them, ask questions, get advice, learn how they deal with challenges and tough situations.

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The Results of Doing One on Ones Right

I changed my mindset from...

"How can I talk slowly about enough dumb things so that the meeting ends"

to...

"What questions do I want to ask today to help me grow, learn, and develop skills so that I can one day do their job"

And I saw a massive change in my results.

I got a promotion to senior software engineer basically as soon as I started asking better questions and focusing on growth and leadership instead of raw code output and productivity. Then I got a 25% raise, followed by another 10% raise the next year. For better or for worse, LinkedIn recruiters see the recent promotion too and won't leave me alone.

I was always thinking productivity and code was what managers wanted from me. It's not.

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How to Get the Most Out of Your One on Ones

Prepare Questions & Topics

I always spend at least 15 minutes before a one on one to carefully think about what I want to dive into and learn.

If I struggled with communication or personnel issues with a teammate, I bring it up and ask how they would have approached the situation.

I get a lot of thoughtful insight from doing this and can go into more situations with my manager's advice in the back of my mind.

Write Down Notes During the Week

I have a special tab in my notes app for each person I have one on ones with. During the week as things happen, I leave a few notes for myself to bring up in my next one on one.

It's much harder to try and recall everything that happened at the end of the week. I would highly recommend you attempt to makes notes as things happen during the week instead.

Review Your Calendar

Check you calendar and see what you did over the last week or two.

Doing this reminds me of important things that happened. Talking through them or asking how my manager would deal with a similar situation is hugely beneficial.

This practice also opens opportunities to talk about how your time is spent. If you notice you've had more meetings than usual, call it out. Maybe you notice a lack of meetings and call out that the team should be collaborating more, call that out too.

Take time to reflect on your calendar and how you spent your time and you can learn and improve on it.

Don't Waste Time

I tried to waste time in my early one on ones.

I didn't want to be doing them and they felt awkward and forced. As a result, I got no value from them which made me not want to do them even more. If you feel that you really have nothing to talk about it is better to cancel that session and save both you and your manager time.

Ideally your preparation before will lead to some questions or topics that you can ask for advice about. None of us are perfect and thinking you can't improve or learn from someone with more experience is very naive.

Prepare for your one on one (even just a little helps) and if you truly run out of topics you can end early and save some time anyway.

Closing Thoughts

Cherish your one on one opportunities.

They are not a forced meeting between you and your boss to make sure you are happy and stick around a while longer. One on ones are your opportunity to learn from someone who has been where you are and faced most of the challenges you have yet to face.

Remember, you are getting paid to talk to a mentor.

Take advantage of this opportunity and you will level up as a developer by doing so.