What Makes a Great One-on-One?

Shubhro Roy

Senior Manager at Box



What is the best way to see eye-to-eye with a report as their new manager? One-on-ones are one of the most immediate sources of information about what goes on in the world of your team. They provide another dimension to the way that you communicate with each associate, both collectively and on an individual basis.

I’ve seen a lot of people fall into this pitfall where they feel as though they know nothing about what it takes to conduct a one-on-one, but it is something to be mastered throughout the course of one’s career. Investing time into your one-on-ones will get you and your reports to a place where leading them to become a natural thing.

Actions taken

The first few times that you meet with somebody one-on-one, your demeanor should be friendly, just like when you’re chatting with a friend. You need to connect with them at a human level first and establish a sense of trust.

If you can, schedule thirty-minute blocks with each member of your team weekly or biweekly. They will bring you feedback about what’s going on and will be able to tell you how they’re doing and feeling. You have a chance to inquire about any projects that they’re involved with currently, as well as solicit feedback for yourself as a manager.

Before, you were part of a team yourself, focusing mainly on the tasks that you were assigned. When you become a manager, however, this limited field of view will not be enough. You need to be aware of all of the other projects going on throughout the organization. The most direct source of information will be your teammates, the people working on these projects themselves.

Hey, what are you working on? Oh, this project? Let’s talk delivery. What will our impact be if we succeed? Are there any roadblocks you foresee? You will be able to get an idea of how engaged they are with their work and whether or not they feel challenged by it. Sometimes it also helps to explicitly ask what their engagement level is on a scale of 1 to 10. Keep track of this metric over time and it might just help you identify a gradual disengagement trend before it leads to attrition.

These are not difficult discussions to have; terms like “EQ” can throw people off a little bit. They see this big, confusing skill set that they aren’t sure how to approach. It’s a human thing. You just need to figure out how to access it when you’re talking to people. Regarding them as a peer can help a lot.

Once you have a sense of trust established, make sure you set aside at least a quarterly one-on-one to discuss performance and growth with your direct reports. It's better to provide continuous feedback than wait for yearly performance check-ins which take them by surprise. Timely feedback is crucial for the growth of your team members and ensures they are not caught by surprise during the end-of-year conversations.

Lessons learned

  • Starting one-on-one by telling your report that you’re going to talk about career development is a very top-down way of approaching the session. Instead, you need to get on their level; make it clear that you are here to help them in their journey, not to simply tell them to do something. Ask how you can help them.
  • Schedule your 1:1s in such a way that you don't have a meeting immediately before or after it if possible. This will reduce the chances of rescheduling your 1:1s often or having to cut them short. If you do miss a 1:1 make sure to reschedule it at the earliest. This shows your team that you take them seriously and they will thank you for it.

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Shubhro Roy

Senior Manager at Box

Leadership DevelopmentCommunicationLeadership TrainingMentorship ProgramsPerformance ReviewsFeedback TechniquesCareer GrowthCareer ProgressionIndividual Contributor RolesTeam & Project Management

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