It’s my favorite part of managing people and undoubtedly the most satisfying and memorable part of my career: meeting with people one-on-one. It might even be the key to growing teams and building successful businesses. For me, a one-on-one is getting to know someone, figuring out what makes them tick, helping them learn how to adapt and excel, and, even better, watching them grow and advance. Ultimately, the countless hours I’ve spent cultivating meaningful conversations and relationships have nourished me personally and taught me how to be a better leader.

The workplace can be messy and noisy. It’s filled with people who have loud concerns and opinions about projects, processes, and people, among other things. And while there’s certainly a place for lively, constructive discourse, it can also run the risk of burying the individual voice.

My main goal in every one-on-one is to give every voice, especially the smallest voice, a chance to be heard. But the smallest voice often needs time, tenderness, and trust in order to speak. That’s why I think the following guidelines are important.

Consistency is key, so I establish a regular cadence

Because one-on-ones don’t generally represent a fire that needs to be put out, they can sometimes seem insignificant, but every time I miss, ignore or push back a one-on-one, I risk communicating that my coworker is a low priority. That’s why I think one-on-ones should happen at the same time on the same day each week. Consistency, despite whatever crisis or hurdle might come up, helps reinforce my commitment to an individual’s thoughts, ideas, concerns and victories. Sure, sometimes I need to reschedule, and that’s ok, but if it becomes the norm, it’s clear I need to find a new time slot that works.

I don't rush my one-on-ones

Establishing compassion, trust, and authenticity takes time, and that's why I schedule my one-on-ones to be at least 30 minutes and ideally 50 minutes. The first 5-10 minutes are generally spent on a “How are you?” or “What’s on your mind today?” to help me figure out where someone is mentally, physically, and emotionally. This intro time also helps to build momentum that ideally leads to a meaningful conversation. If my one-one-one is 15 minutes, it’s not a one-on-one, it’s a check-in. All they will learn is that I don’t have time to care, and, because I as a leader set the emotional tone for the company, this could be a slippery slope.

It’s best when I reduce distractions and show that I'm listening

Most of our team is distributed, so I use Zoom video for the majority of my one-on-ones. Working in a distributed company means I’m on a lot of video calls. I’ve come up with a bunch of little tweaks to help with attentiveness and mindfulness during the call. It is important to show that I'm actively listening.

I look at the camera often. When I'm in person I look at people’s eyes to show them I'm listening. Doing that on a video call requires a bit of counter-intuitive body language by looking at the camera. I'm looking at the camera not at the person, but they’ll see me looking directly at them. It’s a subtle difference but I’ve found it highly effective.

I also try to place the video call window up the screen towards the camera. I also decrease the size of the window so the person’s eyes are naturally closer to the top of the window (closer to the camera). When I'm not looking at the camera while the person is speaking, it’ll still look like I'm generally looking at them because their video is closer to the camera. When I see someone’s eyes darting around during a call, it’s easy to assume they’re distracted.

I actually listen. I don't get on a video call unless I can be sure that I can give the other person my full attention. There’s nothing more dismissive than seeing people on the call absorbed in something else. I try to give the speaker visual cues that I'm listening, including the occasional nod. I mark myself as do not disturb and turn off all notifications and distractions.

I show my hands. Once in a while I’ll lean back or do something to have my hands show on camera. This can be a simple thumbs up sign when I'm in agreement with something that is being said. This shows that I’m not typing and is another visual cue that I'm paying attention.

I take written notes. Hand-written notes force me to not use the keyboard and further pay attention. I generally let people know I like taking hand-written notes so they know why I look down once in a while. Sometimes looking down can be disruptive particularly in one-on-one video meetings as conversations will naturally pause.

I make sure my lighting, sound, camera are good. I double check that I'm properly lit, and I don’t have a light behind me that’s washing out my image. When necessary, I use a headset or headphones to prevent feedback. I try using a higher quality microphone instead of the built-in one. I make sure my camera is good quality. Looking and sounding good helps eliminate distractions from any message I'm trying to convey.

I turn off my own video preview. I turn off the little window showing my own live view once I've confirmed that my lighting is good. I find that once that preview is gone, I look more at the person on the other end of the call.

When possible, I’m a fan of the walking one-on-one. The advantage of working in Los Angeeles is that the weather is almost always perfect, and I’ve noticed that it’s easier to let my defenses down when I'm walking along the beach or in a local neighborhood. Walking gets the blood flowing and helps clear the brain for creative thinking.

If walking isn’t an option but the meeting is in-person, then a meeting space is a good alternative, but the space needs to be comfortable and private enough to have a confidential conversation. If the meeting is in a shared space, like a restaurant or coffee shop, forget it. I’ve found that when food or beverages are introduced in a setting where others are around, there’s just too much distraction. It’s great to schedule social time with your team, but don’t confuse social time with one-on-ones.

Then I listen and watch for signals

From the moment the meeting starts, I pay attention. When I ask “How are you?,” it’s key to notice what happens next. Long sigh? Quick “I’m great”? Silence? Smile? Eyes look down? Shoulders drop? Body language and tone of voice says everything. In those first moments, my coworker very likely communicates what they most want to talk about. It’s my job to pick up on those clues and properly open or steer the conversation.

I don't have an agenda or format, but I prepare

A one-on-one is not a project meeting or a status report. Rather, it’s a personal and professional development goal-setting and plan-of-action session. In a recent one-on-one I had, my coworker started with a walk-through of a project list in a spreadsheet. But rather than get pulled into a task-oriented conversation, I shifted the line of questioning by asking what was working, how he was doing, and what was hardest about the project? This allowed me to be able to pull back and start probing about his longer-term objectives.

As the manager, it’s my job to know the near-term, mid-term, and long-term goals of each of my team members. Before the meeting, I try to make sure I’m up-to-date on the status of their weekly, monthly, and quarterly milestones. I have the 12-month roadmap in my mind and know the top 3-5 objectives we’re trying to solve. I also make sure to have the relevant KPIs related to that individual in my mind. I have a shared doc for every person I do one-on-ones with where I keep track of topics, action items, and notes. If it’s hard for me to quickly get this information, there are process issues that need to be solved within the company, but that’s another post. The point being is that it’s my job to stay informed so that I can help when or if things get stuck. With this information, I can help to avoid common pitfalls before they happen, and I can more easily recognize patterns and prevent problems from arising.

I ditch the technology during the meeting

As I already mentioned, I think writing in an old-fashioned notebook is great. It allows me to take notes about my conversations but in a more personal way. If one-on-ones include typing into a computer or if I'm reaching for my phone, then it’s usually not a one-on-one; it’s more likely a project meeting. After the meeting, I translate some of the notes to the shared doc.

I follow-up promptly on open items

I consider all of the listening, questioning, and discussion that happens during a one-on-one to be managerial preventative maintenance. When I’m really paying attention, I see when interest in a project begins to wane or when conflict is beginning to bubble, and I can take action before people become disengaged, uninspired, tense, or angry. The benefit and reward of creating a culture of healthy one-on-ones is a distinct lack of drama and an increased sense of job satisfaction.

I've found that creating trust leads to candor

It’s simple: by establishing a regular cadence and by following up on items and issues, you will establish a trustworthy pattern and an environment that allows for increased candor. Of course, it’s a shared responsibility between both participants, but if the right level of care is established and remains consistent, you’ll find that even when you have to have tough conversations, you’ll both look forward to the one-on-one time.

On One-on-Ones