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Running One on Ones with Your Remote Employees

You don’t have to look too far to see the benefits of one on one meetings between managers and their direct reports being touted across leadership blogs, twitter threads and studies looking into the workforce. 

Gallup’s State of the American Manager report reveals that employees who have regular meetings with their managers are almost three times as likely to be engaged as employees who don’t. A Forbes article shared that “one-on-ones are one of the most important productivity tools you have as a manager.” And Wavelength dubbed it, “the most important meeting.”

The benefits don’t change when our teams are distributed. In fact, they may even increase as it could be one of the only regular times you’ll see your team face to face (that is, through video chat, of course!)

Of course, taking a one on one online isn’t as simple as downloading Zoom and sending a calendar invite. 

To help make the transition a smooth one, we asked Marcus Wermuth, an engineering manager at Buffer, to share his advice. Earlier this year, Marcus wrote a guide on his blog covering this topic and as a manager of a distributed team spanning various time zones from Taiwan to the West Coast of the US he has a fair few experiences to draw from. 

Logistics of Running a Virtual One on One

The main difference between in-person one on ones and their virtual counterparts is, of course, the fact you won’t be meeting in the same location. One or both of you may be taking the call from home or some other casual setting, and you are relying on technology and tools to facilitate your connection. 

But just because you don’t have to book a meeting room ahead of time or scout out a coffee shop offsite, doesn’t mean you shouldn’t still think about the location of your virtual call too (even if it’s just initially). 

“I know I’m a bit extreme with having lights and having a mic and all that but having a good set up even if it’s just good headphones is really important,” Marcus says. 

For your one on one meetings to go smoothly, you want to create a safe and welcoming environment that fosters trust and vulnerability. Everything from lighting to background noise and whether you’re interrupted or not all contribute to how comfortable you and your report will feel during the meeting. So, it’s essential to get these right. 

Consider taking these meetings in the same location, or at least one that’s easily controlled. You’ll want a reliable internet, a way to switch up the lighting depending on the time of day (and weather) and possibly to mute your notifications to avoid distractions. 

“Not having a thousand windows open, not having your phone and continuously checking it [all help],” Marcus says. “While that sometimes happens in person, in a video call, it’s even more obvious when you do that.”

It may seem like there’s more to think about when taking these meetings online, and that may be true in the beginning. However, like all skills — once you learn how to do it and it becomes second nature, it won’t feel like effort at all. 

“People think that by not having the person in front of you you’re missing out,” Marcus says. “But, actually I can’t say that at all.”

Scheduling Your One on One Meetings

When you aren’t working in the same building as your direct reports, there are fewer opportunities to connect incidentally throughout the week. In other words, you can’t have a quick catch up in the breakroom or ask about their family in the elevator each morning. 

This means you have to rely on more scheduled forms of connection — team meetings, slack channels or any company initiatives like social calls or all hands catch-ups. 

Of course, these don’t always lend themselves to more in-depth conversations in the same way a one on one meeting does, and you may find you need them more often in a remote role. 

However, as with most things, there isn’t a one-size-fits-all approach to this. How often you should implement a one on one meeting depends entirely on what else you have structured in your weekly schedule. 

Do you already have daily video calls with your direct reports? Or do you rely mostly on asynchronous communication? Are your other meetings short, task-orientated run-throughs? Or is there an opportunity for small talk and checking in? 

Marcus is an advocate for a weekly one on one meeting. 

“Due to us being very async, this one on one is a very important meeting because this is sometimes the only time that I get to see this person visually and get to connect with that person,” he says. 

“The weekly sometimes sounds like it’s a lot, but it helps to know if something comes up tomorrow, we’ll talk about it Wednesday [rather than having to wait weeks].” 

Other teams that may have more face-to-face communication and other opportunities for connection may find bi-weekly or monthly meetings sufficient. 

What is essential is ensuring you prioritise this meeting (whenever you schedule it). Whether you set up a recurring calendar invite for a specific time or ensure scheduling the next meeting is a rolling agenda point, it’s important not to let it slip through the cracks.

Preparing for a One on One

In your first one on one with a new direct report, you should carve out some time to discuss how you want to structure your subsequent meetings. 

Are you both people who like to have a structure to work through or more go with the flow types? 

Is it easy to come up with topics, or are you struggling to find things to cover in each meeting? 

The answers to these kinds of questions will allow you to create a plan that works for you both as well as allowing you to set expectations early on. 

It’s important to remain flexible and open — this meeting is about relationship, not ticking off tasks from a list. 

“It’s a human thing, it’s not a robotic thing,” Marcus says. 

Setting up an Agenda for Remote One on Ones

The aim of one on one meetings is to give you both time outside of the regular day to day, task-orientated, work environment to connect and talk. What you cover in these meetings will likely vary, but is often a place to catch up about non-work related topics, share about any challenges or concerns, provide and receive feedback and talk about career development and goals. 

As I mentioned above, personality type and preference will affect how you approach these topics and how structured you’ll want to be. 

Many managers jump in without much thought, wanting the conversation to flow naturally. While this can definitely work for people who are forthcoming and find it easy to talk, the open slate can work against others who may not know where to start. 

According to Fellow’s definitive guide, The Art of the One-on-One Meeting, there are a few different approaches you can take when leading a one on one — and therefore different ways to set up your agenda. 

They offer three options, but obviously, you can make as many tweaks as you like to make this your own. 

The 90/10 Format 

This approach puts the ownership firmly in the hands of the employee. They take up 90% of the agenda, while the manager brings the remaining 10%. 

Marcus uses this method and says it’s important that the direct report knows this meeting is “for them.” 

“They own the agenda, and they should bring most of the topics to the table,” he says.

This approach works well for those who find it easy to fill up an agenda each meeting. You can break up the talking points into two sections — one for each of you — with 90% belonging to the employee and 10% to the manager. 

The Key Areas Approach 

The next option that Fellow suggests is letting a list of key areas guide your agenda. They offer a list of eight topics that can act as headings or prompts for questions each meeting. 

  • Top of mind
  • Things that went well
  • Learnings
  • Priorities
  • Challenges and concerns
  • Team dynamics
  • Feedback
  • Career development

Some other suggestions: 

  • Personal updates 
  • Project reflections 
  • Goals 

This approach is useful for people who need a bit more structure or who find it difficult to think of discussion points. 

You may like to set up a recurring agenda note with the headings included. Then you can both add in specific questions, issues or subheadings to cover ahead of each meeting. This gets you thinking and reflecting ahead of the meeting. 

The Chronological Style 

Instead of structuring your meeting agenda by topic, you may prefer to structure it by time. 

Fellow suggests following a template of past wins and challenges, immediate priorities, and future opportunities.

This structure means you can start a meeting asking about their week or even something that was mentioned in the previous session. The move onto current priorities, learnings or challenges and finish up discussing goals and development. This more general approach can still encompass many of the topics mentioned in the key areas approach, but it may flow better for some individuals. 

“It’s a very personal thing,” Marcus says. “There are people in my team that always bring a long list, and we barely make it through. There’s other people who have maybe two things on it, and we’ll spend the whole time on those two things.”

Contributing to the Conversation and Actively Listening

Now that you’ve decided which method to utilise — and how you’ll set up your recurring agenda — you have a template to prepare. 

Look over the list ahead of time, think about the talking points — are you across the projects or tasks they may be mentioning? Are there any resources you might need handy? Pull them up, so you’re not wasting time searching for them in the meeting. 

If there doesn’t seem to be a lot of topics on the list this week, you may like to quickly think of some items to add or have up your sleeve if you have extra time. 

“I would always say to be careful with those blog posts that are like, “100 awesome one on one questions,” Marcus says. 

Instead, Marcus prefers to remain specific, perhaps revisiting a topic from a previous one on one or asking after a project or particular struggle or goal. 

Though he does admit, he does occasionally use a card game which produces random topics and questions. 

“I bring them into it by asking them to pick a number between one and 48 and I draw the card,” he says. “They have secondary topics too, and it’s not just asking the question and waiting for an answer and ok done. You’re kind of hoping that conversation stems from it.”

When it’s time to chat about career progression, Marcus says preparation is key. You’ll need to look at their past reviews, match their level against career frameworks and come ready to provide feedback on what to improve. 

However, Marcus maintains the most important thing a manager brings to the meeting is listening skills. He’s even written an entire article on active listening.

It’s not just about giving them space to speak — though that is, of course, important — but actively engaging with what they’re saying and conveying that back to them. Things like eye contact and verbal recognition (saying, yes, ah, hmm) are beneficial. So is following up with questions or confirming you understood by repeating it back to them. 

When meeting virtually, you’re almost stuck in a face to face position. There’s less opportunity to shift in your seat or take a walking meeting that can, in some cases, alleviate discomfort around speaking vulnerably. You might like to pause and thoughtfully turn your head to the side before answering questions or have a glass of water nearby to take a sip to break any tension and allow some space. 

Structuring a One on One Meeting

“There’s a certain structure that I try to keep to,” Marcus says. “For the first 10 minutes, 15 minutes, what we’ll do is check-in — ‘how’s life? You bought a BBQ yesterday, did it work well? Or what game are you playing? Or, how are the kids? All those things you can get at least a little window into their lives.”

After that period he’ll then launch into the agenda points, but finds these initial talking points invaluable in developing relationships with his direct reports. 

“Understanding more about the other person’s life, knowing what context they are in will help you to up your game when it comes to listening to thoughts or challenges of the direct report,” Marcus says. 

Building Connection and Trust with your Remote Employees

Developing an open and trusting relationship with your direct reports doesn’t always come naturally. When you’re potentially living in different countries and time zones, this can be even more difficult. 

Developing an engaging connection is undoubtedly one of the main benefits of one on one meetings. Having a space to get to know each other outside of work tasks, be vulnerable about struggles and future goals, and share feedback can all contribute to the strength of trust and connection. However, this doesn’t just happen automatically, and the initial steps can be daunting, if not downright uncomfortable. 

“It’s hard, you don’t get there with just one click of your fingers,” Marcus says. “What I will say is, it’s not just happening in the one on ones. It’s mostly happening elsewhere.”

The one on one meeting makes up only a small percentage of your week or month, and you’re bringing into the session all of your other interactions too. If there has been no effort elsewhere to create a supportive environment or you’re constantly breaking trust by forgetting to do things you said you would, running late to meetings or being unavailable to help, it’s unlikely your direct report will easily engage in the one on one. 

Even if most of your other communication is asynchronous, there are still ways to increase trust within your team. 

Marcus is a big advocate for leading by example. “Show your team you’re human too. You’re not this manager person who is high up there looking down on them,” he says. “Saying, ‘oh I messed that up, or I did this wrong.”

By being authentic, it shows your team that they are free to be themselves too. 

“Then, whether you’re on a video call or you’re at the retreat and doing a one on one it doesn’t matter,” Marcus. “If you have the trust, it will work.”

Taking Notes and Concluding One on Ones

“After active listening, taking notes is probably the second most important thing,” Marcus says. 

He recommends taking some time after the meeting has ended to take note of any items that need actioning, items to come back to the next meeting or anything you might need to remember. 

These can go directly into the next meeting’s agenda, onto your own weekly to-do list, or somewhere you take more reflective notes — wherever fits. Depending on your software of choice, the action items could be in a shared note with your direct report so they can see when you complete your tasks, and add in their own as well. 

Action items are important because they are a tangible expression of your support and therefore showcase the state of trust. 

When the meeting covered more in-depth topics like career progression or feedback, Marcus may also send a summary to the direct report. 

“Everyone has different ways of understanding and learning,” he says. 

He also recommends taking an extra five-ten minutes (so ten – 20 minutes total) before scheduling another meeting to catch your breath and prepare. This may seem obvious, but when you don’t have to switch rooms or can’t pop your head into someone’s office to say, ‘just getting some water — see you in there!’ you have to be intentional about giving yourself small breaks. 

Taking your one on one meetings online doesn’t have to change your entire system. You likely already follow a loose schedule, use an agenda and aim to build trust throughout the week. However, as with most things when you go remote, you may simply need to be slightly more intentional to get the same impact (at least initially). 

But when the reward is engagement, connection and a well-adjusted team, we think it’s worth it. 

– Bree Caggiati

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