How To Make One-on-Ones More Exciting

Karthik Gandhi

Senior Engineering Manager at Stripe



At the beginning of my career, one-on-ones were mainly about chatting. If a person was more gregarious and outspoken, the conversation would take its jovial course, but if they were reserved or reluctant to talk about personal life, the conversation would stall. That approach would make me connect more with a more talkative or sociable group, which I thought was not fair. People on the team should be appreciated for their contribution and not their personality. That challenged me to come up with one-on-ones that would give everyone on the team an equal opportunity to speak up, either online or asynchronously.

One-on-ones should have its purpose other than chit-chat. A chit-chat can help develop personal bonds, but then we are talking about means and not the purpose. Their purpose, in my opinion, should be to help reports be more productive, help them in their career development, and coach them to untap their hidden potential. I wanted to structure and standardize one-on-ones to make them more beneficial to different people on my team with their different personality types.

Actions taken

My one-on-ones are structured to include three parts:

Planning for personal growth

This part of the conversation should focus on a particular person and not on what they do in a company or team. I would initiate a candid discussion about their strengths and areas of improvement and their competencies in various domains. For example, if they are engineers, domains would range from distributed systems and back-end to project management, programming languages, and process development, to name a few. I would have them self-assess their competencies rating them with 90 points if they are doing great or 100 if they could write a book on a subject matter, but most would be rated somewhere much below that. I would also ask them to share with me the rating they would aspire to accomplish. Based on their responses, I would develop an annual plan, typically in January, coupled with quarterly goals.

My approach proved to be particularly helpful in situations of severe attrition where people thought that a company treated them as expendables. By focusing on their career and growth, they had been sent a clear message that the company cared about them. Moreover, these conversations gave me valuable insight if some people were in the right role or company altogether. If someone was complaining about everything and everyone, chances were they were not satisfied on a deeper level and that those complaints were just symptoms of a more serious, underlying problem. I was often able to detect these underlying problems through one-on-ones and be honest with my reports about their future on the team/with the company, knowing that their expectations would not be met.

Preparing for performance reviews

I am one of those managers who tend to praise in public and criticize in private. As a result, people wouldn’t acknowledge my criticism with the seriousness it deserves because it was raised within the boundaries of a personal conversation. To avoid this, I decided to make my criticism more explicit and part of one-on-ones. That way, I was able to address my concerns timely and avoid an element of surprise during the performance reviews.

The conversation in this section would branch out into two streams: how they are doing against their own level and what it would take them to get to the next level. I would also discuss with them if they would rather pursue a manager or IC track and what in each case it would take to get to the next level. I would have them write down all the things they were doing and compare them against the next level requirements. If they think they already met the requirements, they should mark it green, orange if they would need to make some improvements, and red if they were nowhere near accomplishing them.

Tracking quarterly goal

To start with, I would give my reports a template to fill in and compare their quarterly goals with mine. As a manager, I would share with them what I would work on in the upcoming quarter, and I would want them to align on those goals as much as possible. Of course, nothing would be set in stone, and I would encourage them to add a comment at the end listing things they would de/prioritized or additional activities they would help other teams with. That would help me benchmark if a person were delivering their goals.

Lessons learned

  • One-on-ones should be more than a casual conversation. They only become exciting when they serve their true purpose, which is to provide you as a manager an opportunity to connect with your reports and help them grow. When structured that way, one-on-ones never become boring.
  • The leading cause of attrition is an element of surprise during performance reviews. Deliver regular feedback, on the spot if possible, no matter how difficult or uncomfortable that could be. By doing so, no one will be surprised during performance reviews.
  • Developing a personalized career ladder with a clear scope and impact is rather difficult. It will take at least a few iterations to align a person’s goals and aspirations with the existing opportunities and company goals. Not to mention that I would take time to get to learn about the person and their capabilities.
  • If you decide to write a performance review at the end of the performance cycle, be aware that you may forget some things. Instead, start early and keep track of every single thing. Also, it will be safe to assume that those reviews will be read by people who had no slightest idea about the context. Feel free to add all the context, links, and references that you feel will be helpful.
  • If I noticed something out of line with what my reports want to do in their careers, one-on-ones would be a great opportunity to call them out on it. If someone told me that they aspire to become a project manager and I would happen to notice that they are not doing a good job managing their current projects, I would make sure to bring it to their attention. One-on-ones are the perfect venue to deliver that kind of feedback and help people align with their long-term goals.

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Karthik Gandhi

Senior Engineering Manager at Stripe

Performance ReviewsFeedback TechniquesCareer Ladder

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