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Providing Better One-on-Ones

Goal Setting
Coaching / Training / Mentorship

21 July, 2021

Jibin Jose Jose
Jibin Jose Jose

Senior Engineering Manager at

Jibin Jose, Senior Engineering Manager at, takes pride in his approach to managing each member of his team on an individual basis.


As a manager, one of the first big lessons that I needed to learn was how to give a real one-on-one. What is a manager supposed to do during one of these meetings? What are we supposed to talk about?

I started to do a lot of research into the topic. I asked for a lot of advice from some of the great managers that have mentored me in the past, as well. It took some time to get used to the practice of it. Eventually, I realized how valuable one-on-ones are when familiarizing yourself with the people on your team.

Actions taken

I’ve seen a lot of new managers put too much pressure on themselves to deliver the perfect one-on-one. They end up making the process really complicated, much more so than necessary. This may be due to stress or inexperience; you enter a mindset where you suddenly feel obligated to solve everybody’s problems, all at once. The intention is good, but this is the wrong way to go about it.

A common misconception is that a manager needs to be able to answer every question up-front. Some managers may be too embarrassed to reveal any indicator of weakness or uncertainty. They place a lot of value in accuracy, when, in reality, the most important part about the one-on-one is the trajectory of the person in front of them.

When you set these expectations for yourself, it will be much more difficult for you to open up to your report authentically. What should a leader’s attitude be when entering a one-on-one? My opinion in this area has not changed much over the years.

My advice to the reports that I meet with: know the job very well. Most organizations will provide a very explicit definition of what a given position entails. Being very familiar with these requirements puts them in a good position to succeed within the company. I emphasize that the most important part of their performance is how they approach these responsibilities. They are always able to train themselves in any areas that challenge them professionally.

Another pitfall that many new managers fall into: they enter the one-on-one with a rigid itinerary, following it to a T during the meeting. Some of them may even bring the same “checklist” into meetings with all of the people that they manage. This is a terrible habit. You need to engage with the person in front of you, not a list of deliverables or metrics.

This is where flexibility comes into play. Having a list of topics to fall back on is perfectly acceptable; always be willing to deviate from this list if something more important comes to light during these meetings, however. It has to be a candid conversation. Your people will feel suffocated if you focus more on what you have to say than on what they have to share with you.

Showing empathy within twenty minutes’ time is not an easy thing to do with somebody who you barely know. An excellent manager is able to build a bridge and to establish a healthy, functional working relationship. Show the person in front of you that you care. Be objective, but always show kindness.

Lessons learned

  • My advice is to start casually. One-on-ones, by definition, require you to be open with the person in front of you. Listen intently to what the other person is telling you. False promises should never be given in lieu of something more substantial.
  • At first, don’t talk. Just listen. Avoid interrupting, and take notes when necessary. Ask specific questions and offer actionable advice. After your first few meetings, things will become much easier. You will need to deliver your fair share of difficult conversations, but to avoid them would be to allow the underlying problem to grow.
  • I learn new things about my team every time that I meet with them. I hear new concerns from people who have been working under me for years. Sometimes, these revelations are shocking. There is always something new to hear.

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