One-on-one meetings

Posted by Douglas Drumond Kayama on March 28, 2021 · 7 mins read

You can’t simply gain trust by saying “trust me, I know what I’m saying”, you have to earn it. Let’s start discussing trust and then how to conduct one-on-one meetings to earn that trust.


In The High Price of Mistrust, a book titled Bowling Alone, by Robert Putnam, is discussed and there are two parts I’d like to quote as they relate to remote management:

“One key lesson we can derive from Bowling Alone is that the less we trust each other—something which is both a cause and consequence of declining community engagement—the more it costs us.”

“Mistrust drives us to install remote monitoring software on our employees’ laptops and ask them to fill in reports on every tiny task to prove they’re not skiving off.”

Surveillance is an attempt to control the team. That’s the wrong premise, you don’t have to control the team, you have to build trust, provide directions and trust the team will do the right thing. And to build trust, first you start building relationships. But how to do that without face-to-face interactions like you had at the office? One-on-one meetings are the key to that.

Why one-on-one meetings

At Google, it was believed that to be a good engineering manager, having deeper technical expertise than the team was needed. Still, what they found through Project Oxygen, a 2009 manager research project, was that the most valued managers were the ones who made time for one-on-one meetings.

Know Your Team, a software company focused on team development, did a survey in 2018 with a similar result: they surveyed 1182 managers and 838 employees, and found that 89% of the managers and 73% of the employees said that one-on-ones positively affected a team’s performance. However, 40% of employees think their manager isn’t prepared for one-on-one meetings.

Engagement through dialogue

Ongoing dialogue creates engagement. Dialogue is an opportunity for managers to show they care about their team.

According to Don Clifton in the book First, Break All the Rules: What the world’s Greatest Managers Do Differently, caring is one of the twelve key items to measure the strength of a workplace. But to show they care, managers need to listen to employees’ answers. Kurt Deenan, a Gallup consultant, says “managers need to listen to their employees, not just talk at their team. Managers create a sense of engagement through conversation.” Communication problems are often the cause of why teams have a low perception of how much their opinion counts.

That does not necessarily need to happen in a formal one-on-one meeting. It may happen through serendipitous encounters. Managers need to be listening all the time.

However, one-on-one meetings are remarkable to gauge an employee’s sense of connection and set expectations. It’s a suitable way to know the person’s strengths, thus making it easier to match their talents to a role and increasing performance.

How to conduct a one-on-one meeting

Block your schedule

Although the frequency you hold one-on-one meetings vary according to the size of the team, the experience of the employees or even the distance in the org chart (it’s unlikely the CTO will hold as many one-on-ones with the developers as their direct managers will), it’s important to keep them recurring. Experiment with the frequency, but do not cancel the meeting.

Be prepared

It’s your employees’ meeting, they should bring a list of points to discuss, but that doesn’t mean you shouldn’t be prepared. In the ideal scenario, both of you would work jointly on an agenda, but in case that’s not possible, write down your own list too. Compare the lists, prioritize and make sure you cover the most critical issues.

Be present

Turn off your notifications and close your notebook. If it’s in a remote environment, block off distractions, let your video call software fullscreen and pay attention. The only exception is if you agree with your employee you’re taking notes in the meeting. That being so, split the screen with only your video call software and your note-taking application.

Do not use it as a status report meeting

You can use one-on-one meetings to solve problems, but keep it as a more strategic problem-solving. It’s not a status report meeting, if you need to learn the status of some task, use a work management software (such as Pipefy) and check there.

Ask open-ended questions

Good open-ended questions lead to substantial answers. A “how are you?” question seems vague, try instead asking specific questions with open-end answers. For instance, “what’s the favorite part of what you do and what’s the least desirable one?” followed by a “why is that so?”


It’s important you keep a record of the meetings so you don’t miss anything. If you constantly miss what your employee is saying, you send the wrong message.

There are several tools that can assist in your one-on-one meeting. You can keep a shared document on Google Docs or other office tools (remember you can also have your private notes), but you can also take advantage of your work management tool. Using Pipefy, you can set up a one-on-one pipe (there’s a template for that) to keep track of every meeting.


In the office, it’s easier to have water cooler chats and serendipitous encounters where you can start building relationships with the team. In a remote environment, we need to rely on other methods to build those connections. One-on-one meetings are one of those ways and it’s highly associated with the effectiveness of a manager by their employees. There’s no exact formula for a successful meeting, but some simple rules make it more fruitful. Engage the team and see a boost in productivity and morale. Trust me, I know what I’m saying.

Photo by Charles Deluvio on Unsplash