What Makes the Perfect One-on-One?

Tushar Dadlani

Principal Product Manager at Tushar Dadlani



It’s easy to question the need to talk to any person on your team. What’s changed, is there a point? There will always be something new to learn from one of these meetings. Even if there is nothing really to talk about, you have a chance to discuss where your current project is headed and what there is to do next. Sometimes you will try to pull out concerns, only to find that there are none.

There are certain disagreements, on the other hand, that we prefer to be very direct about. Before, I had no process that allowed me to address these issues professionally. Creating transparency in this way, laying out the state of the business and what needs to be done, can be challenging when working with a small team. How can you be as transparent as possible? What do you need to be transparent about?

Person A might care a lot about the company. Person B might care more about the work. Person C might be concerned only with their own career goals. As a manager, you have no way of knowing which will be which until you start conducting your first one-on-ones. What can I tell you, personally? What is your concern?

Actions taken

I try to have very frequent one-on-ones when a person first joins. They lack the social context, and I think that this interest helps them to establish themselves. Once they are able to do so, I gradually begin paring the appointments back to once every two weeks, to once, a month, and so on. No matter how frequent, I make it a point to never miss an appointment.

I, personally, have not found one structure for one-on-ones that fits all of the different types of people that I manage. Each one is different. I’ve boiled it down to a few key talking points, however.

One is an emphasis on responsible time management. I think that this is one area where a lot of employees struggle. I also will make an effort to unblock their way with any resources that I have access to. Avoid being the only person supporting an employee's career; always be looking for new ways to integrate them more thoroughly into your company’s network, and even your own network outside of the company. You delegate a bit of the weight off of your shoulders when you do so.

I am always recommending books to my direct reports. I ask them to read the book, and then we are able to discuss how it applies to the context of our company specifically. It’s a good refresher for me, as well.

Of course, there is the ongoing task of getting to know your employees personally. Sometimes, as managers, we really do not know what our engineers are motivated by. I love asking my employees to share what motivates them. It’s always really interesting to see how this changes as they become more senior within the company. Something is always motivating them to stay. I love to revisit this topic with them. Once they feel safe and compensated fairly, they will begin to grow these roots and develop some of those higher-level objectives.

You always have to be gathering feedback from your employees. Silence on all channels in this regard should never be taken as a good sign. They have thoughts and emotions. You need to do what you can to provide them with a safe space with which to share these feelings. In a group setting, some people in the room may not know your report’s context and intent, so you, as their manager, may perceive them very differently than others might. You can coach them in order to teach them how to express themselves more deliberately, even outside of your one-on-ones.

Lessons learned

  • With a direct report, especially one who you are mentoring or coaching, you’re sort of always thinking about their career. I always make an effort to think of the employee first. How can I really help them on their journey? If the company is not giving them the support that they need, I have to figure out how to support them in a different way.
  • You have access to resources beyond time and money; this includes your network and community. All of your own mentors can help your employees think through these things for themselves. I consider my role to be one where I am constantly directing these resources to my team.
  • Every quarter or so, I will review my employees’ calendars with them. We talk about meetings that feel superfluous and identify tendencies and habits that take them away from where they really would like to be long-term. Are these events really adding value to their career, or have they just signed up out of politeness? Help them to think through where they are spending their time.
  • Sometimes, engineers will be full of good ideas but not necessarily be full of ways to apply them to meet the needs of the company. As a manager, connecting their ambition with the context of the business as a whole will channel this energy constructively.

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Tushar Dadlani

Principal Product Manager at Tushar Dadlani

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