One-on-Ones: How Regular Mentoring Can Boost Your Career Growth

When I started my first real job out of college, I had no idea how to operate in the real world. A university education does very little to prep you for the realities of the business world, even if you were like me and graduated with a business major.

My first year as an IT consultant was rocky. While I had 17 years of school under my belt, the skill I perfected most during that time was learning how to get good grades (as opposed to learning for learning's sake). I was proud of my grades and my test scores. I assumed I would jump into the business world and hit the ground running. But instead I ran headfirst into a brick wall. I had all this information in my head but no idea how to actually apply it!

I continued to struggle to the point where I had a mental breakdown at work, in front of some of my co-workers and the client. I didn’t know it at the time, but I was struggling with depression. And while I did know about my severe anxiety, I lacked the tools to properly manage it.

Throughout my whole life I ignored both my anxiety and depression, pushing it deeper and hoping it would just take care of itself. Impostor syndrome crippled me to the point where I would hide in my cubicle, paralyzed with fear because I couldn’t figure out how to get my work done.

I probably would’ve been placed on a performance improvement plan after much longer, but (as embarrassing as it was) I firmly believe that mental breakdown saved my job. After seeing my struggles boil over, my team realized that I needed help. While my team did many things to help me at that difficult time in my life, the biggest positive change was making a simple addition to my schedule:


Soon after my breakdown, I began to meet with a senior developer on my team. He is a great guy who truly cares about helping others, and he delicately helped me work through transitioning from school to work. We started meeting weekly to talk about how things were going on the project, where I was in my career development, and how I was doing with life in general. We made concrete plans to help me complete my work and grow my skills, and we developed a set of emergency protocols that I could use whenever I started feeling overwhelmed.

It worked brilliantly. A short 30 minute session every week was all it took to change my trajectory and turn me into a solid contributor. I still struggled for far longer than I’d like to admit, but simply knowing that somebody else had my back and cared about my development gave me the hope and energy I needed to improve my skills and finally learn to work in the “real world”.

After that, I made sure that one-on-ones were a part of every team I was on, and by doing that I was able to find the mentorship I needed to make it through the early stages of my career. Even six years into my career, I deeply value my regular one-on-ones, both from the mentor and mentee perspectives. They are an indispensable tool for personal and team growth!

While not all your co-workers will be dealing with problems as extreme as the ones I faced, my story is meant to show just how powerful one-on-ones can be. They can take your team to the next level by helping everyone improve themselves and their work.

If your team isn’t conducting regular one-on-one meetings, you’re missing out on an incredible enabler that will create a better workplace environment, increase your team’s performance, and help each individual reach their potential.

As a consultant I’ve been on a wide variety of teams. In my experience, the happiest, most productive teams all held regular one-on-one meetings. This article will cover (1) why one-on-ones are important to your team’s success, (2) what typically happens during a one-on-one, and (3) how to get one-on-ones started on your own team, whether you are managing others or not.

Why One-on-Ones?

One-on-ones strengthen bonds by increasing the amount of communication you and your teammates have with one another. In the normal flow of business, many of the conversations we have with our teammates are regarding the specific tasks we need to accomplish that day. While those conversations are important in their own ways, what’s typically lacking in the average person’s daily communications is a deliberate forum for praise, constructive criticism, and meaningful dialog.

Sitting face-to-face (or screen-to-screen for remote workers) and having an uninterrupted conversation with another person is a powerful experience. Group conversations are fun, but how often do you do a deep dive into your hopes and dreams in front of a crowd? In order to be vulnerable, we have to feel like we can trust the person we’re talking to. Establishing trust takes time, and it’s often easier to do in conversation with a single person. Regular one-on-ones are a deliberate practice crafted to create a space where truths can be spoken and where meaningful dialog can occur.

That’s not to say that every one-on-one is an intense, soul-searching endeavor where you pour your heart out to a co-worker. Most aren’t! But the regular practice of meeting with your teammates builds stronger relationships so that when the need for a deep conversation arises, it can take place in an environment of trust and support.

Once trust has been established, you can have candid conversations with your co-worker. You can go over your concerns with the direction of your project, give each other constructive criticism, and discuss career aspirations.

What Is a One-on-One?

While there are many different formats for one-on-ones, I personal strive to touch on these three areas:

  • How is the person feeling about their current work?
  • What are their career aspirations?
  • Who are they outside of work?

The first two topics allow people to discuss information about their past, present, and future work life. If their current work isn’t ultimately benefiting their desired career path, this is an opportunity to express that concern and make plans for change. It's also a great time to get help on immediate problems that are blocking your ability to finish your work in a timely manner.

The third topic helps build trust by getting to know them on a more personal level. It’s amazing how little you sometimes learn about a person even if you’ve sat next to them for years. Giving people space to share their passions helps them be seen as a whole person, not just a cog in the machine. In addition, sharing your whole self gives people more opportunities to find common ground and develop a deeper connection and friendship.

These meetings should be long enough to allow for substantial conversations. I typically schedule one-on-ones once a week for 30 minutes. The frequent cadence allows for quick turnaround with any questions and a shorter feedback loop for sharing constructive criticism. However, depending on the needs of your particular team, you could use a variety of schedules. I’ve been on teams where one-on-ones are every other week, once a sprint (if you’re working in an Agile environment), or even once a month. The further apart the meetings are, the longer each meeting should be. Don't let meetings slip any further than a month though, since they're more likely to completely disappear from the calendar and they won't become a habit.

One-on-ones are also opportunities to meet with people at different levels in the company. I've found it helpful to have less frequent — but still regular — one-on-ones with people a few levels above or below you in the organization. I meet with my manager’s manager about once every six weeks. This gives me time to ask higher-level questions about the overall direction of the project I’m working on and valuable face time with people I don’t necessarily work directly with on a day-to-day basis.

How to Start Having One-on-Ones in Your Own Team

If you’re a team lead, it’s pretty easy to start the practice of regular one-on-ones with your team. Send out a few calendar invites and you’re off and running! Make sure to set the context for why a new meeting has taken up their precious time. If you need inspiration, touch on some of the points in this article to help your team understand the importance of one-on-ones.

If you aren’t responsible for others on your team, it’s a little more difficult to start as a team-wide practice, but you can request meetings with your managers and start a personal practice. Encourage your teammates to do the same, and talk to your manager about making it a team practice!

Once you have regular meetings going, do your best to not let them slip off the calendar. Often, one-on-ones become the first meetings cancelled when things get busy, but always try to reschedule instead of completely cancelling them.

In addition, consider which person should own the invite. I like to own my one-on-one invites since they're some of my favorite work meetings so I make sure I never miss one! But if you're prone to ignoring your calendar, ask the person to keep track of it and pester you when you start missing them.

You should seek out one-on-ones with someone who has more experience than you, ideally your direct manager. This gives them a platform to coach you regularly, reducing the likelihood of any surprise feedback on your yearly review. If there are problems with your behavior or areas in which your teammates are hoping you’ll grow, you can receive that feedback here.

Being open to frequent feedback facilitates a culture of mentoring, as people begin to realize that hearing feedback is not an attack on one’s character. In fact, it’s a sign that your teammates care about your professional development. They want to see you grow and succeed!

Finally, look for ways to be both a mentor and a mentee, even if you're a junior member of the team. Everybody has things to learn from and to teach others, so one-on-ones with peers can also be a wonderful experience.


One-on-ones will dramatically change your team's dynamics. By regularly meeting with teammates to discuss current concerns, future career goals, and life in general, you'll forge deeper relationships that will help you work better together. These meetings will help you make friends, see new perspectives, become better at your job, and give you a little break from your day-to-day work.

If you have any other one-on-one strategies that I missed here, please reach out! I love learning new things and adding to my one-on-one toolbox.

This is the fourth of nine articles delving into the processes that every effective development team should use. Stay tuned for more!

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