We know that amazing managers do one-on-ones with their team. But we’re always wondering how they actually go about it. Because one-on-ones are such a personal thing, we know that every manager has their own unique spin on them. That’s why we’re always looking to talk to cool companies about how they do one-on-ones with their team. 

This week, we’re talking to Buffer! Not only is Buffer a super cool social media management platform – it’s also an entirely remote workforce, with employees working in 15 countries (and 11 time zones!).

That’s why we were especially excited to talk to Kara McNair, Engineering Manager at Buffer, about how she has meaningful one-on-ones with her entirely-remote team.

We sat down with Kara to talk about the purpose of one-on-ones, how she prepares, memorable conversations and more.

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Kara’s 1:1 basics:

• # of direct reports: 11 (across 3 teams)
• Office or remote?: Remote
• Frequency: Weekly
• Length: 50 minutes
• Go-to question: “How are things going?”

Building a relationship

I want my direct reports to really understand that my job is to help them be successful and to meet their own goals and dreams. By spending time learning about what matters to them and showing them that I really care about that, they trust me enough to tell me when things aren’t going well for them and giving me the chance to help them.

A codicil to that: sometimes people encounter opportunities that are phenomenally better for them than where they currently are. There are a ton of reasons why that can happen, but I want to be the kind of manager that someone can approach and say, “Hey, my dream job was posted and I am going for it.”

And I can say, truthfully, “Well, yup, I see that. I cannot compete with that, and I care more about you living your best life than anything else, so how can I help?” That tends to breed a healthy situation for the whole team to view each other as whole people, and we can celebrate people “leveling up” on their personal plans.

Understanding how I can help them

This is related to the above, but it also is more tactical. If I have a teammate who is shouldering a lot of server/API work but is really interested in learning more front-end (e.g. React) tech, and has been trying to find time on her own to learn that, if I know that, I can prompt her and the rest of the team to swap and trade task assignments to keep everyone challenged and motivated.

There’s a side benefit for me in that the more each team member learns more about more of the system, the more we reduce our “lottery factor.” It also helps us more effectively sustainably balance on-call and support functions!

Mentoring

This is not a thing that I actively seek out because I think I prefer coaching to teaching. But at the same time, I’ve been at this a while, I’ve developed a pretty good “Ooh, here be dragons” sensor and I can help folks learn how to identify and mitigate risks that they might not know about yet.

Aside from risks, an area I have found that my experience helps folks with is “thinking bigger.” I’m a big-time “looker-aheader” (my boss even said I’m a ✨ at this ). By modelling asking certain types of question-asking, I gather that I help others discover a broader perspective. Some of that is just coaching, but some of it is advice/mentoring too. I love all of it, because when I see people get that “Ohhhh! AHA” moment, I know I’ve saved them pain and grief in future.

"I have personally gotten so used to one-to-ones that it no longer occurred to me that one wouldn’t do them." – @karamcnair of @buffer Share on X

How many direct reports do you have?

As of the end of August, I have 11 direct reports across three teams. That’s really more than we believe to be ideal for a manager, but for a variety of reasons, it makes sense for us to keep this structure for now. In the last four months, I have had six new hires join and we want to make sure that their onboarding/relationship-building is consistent and excellent! What this means is that I balance trade-offs with other responsibilities (project management, interviewing, etc.) with my peers and teammates to make sure that I don’t burn out but we also don’t shortchange Buffer’s priorities

How often are your one-on-ones?

Weekly! That’s been my standard for years, but in a remote team, where you can’t just chat waiting while the coffee machine has blue-screened and is rebooting, it’s really important to maintain these communication/relationship channels on a regular basis.

Right now, with so many new direct reports, I am exploring shortening some of my “established relationship” 1:1s or moving to biweekly for a few – at least until the new folks feel settled and all these relationships are stable

"In a remote team, where you can’t just chat waiting while the coffee machine has blue-screened and is rebooting, it’s really important to maintain these communication/relationship channels on a regular basis." – @karamcnair of @buffer Share on X

How long are your one-on-ones?

My preference is an hour. I have a few regular syncs with non-direct reports for whom it is still really important that we get on the same page with regularly, and we tend to do those weekly, for 30 minutes. Folks who I can go deep with but things are less urgent can be an hour biweekly. It’s amazing how much time we spend chatting in a remote workplace! Amazing and so valuable!

How do you prepare for your one-on-ones?  

One of the things I care a lot about is making sure that I keep track of things my team members have done throughout the week and that I recognize them in our chats. I actually forward Slack convos to my private DM to myself to keep track of things I want to chat about.

I am less organized/more free form than a lot of other managers. My position is that the 1:1 time is owned by the individual and I am here for them. If there are things I need to tell them that don’t need to be “urgent,” I will add them to our agenda (but in a kind way, because I don’t want to blindside folks who might see document updates out of time). That’s part of why I build a private list in Slack rather than updating our shared doc in real-time. Praise can go public in shared doc but any concerns get added shortly before our chat.

I have several people who love to chat and really want to make sure we meet every week, but when we run out of topics will prompt to end the call. Others are more “useless-meeting” sensitive and would prefer not to chat if we have no bullet points on the agenda.

I have found that even if we’re running out of stuff to talk about, preserving space for communication tends to be really fruitful! I’ve regularly found that when our call has gotten awkwardly silent near the end, and we’re kind of dancing around ending it, one of the two of us will suddenly remember something that we really wanted to talk about, but because it wasn’t “purposeful,” it didn’t get on an agenda. I love when these pop up.

What are your go-to one-on-one questions?

It’s a bit lame, but “how are things going?” I also ask them about other interests and seek common ground there.

A team member expressed a love of food/cooking recently on Slack, so we spend time chatting about that. Another bought an off-road motorcycle recently and we talked about how interesting the motorcycle safety course we both took was. This is their time and I trust them to use it effectively. Some days they want to talk career. Some days they want to talk current work. Some days they’re so busy and engaged in current work tasks that they don’t want to spend a lot of time away from that work. Some days, they want to connect on a human level.

"Some days they want to talk career. Some days they want to talk current work. Some days they don’t want to spend a lot of time away from that work. Some days, they want to connect on a human level." – @karamcnair of @buffer on her 1:1s Share on X

What do you do to help your employees open up?

That’s a really hard question for me because it suggests a sense of methodological planning that I simply don’t do. I like my teammates. All of ‘em. I like to help and I want them to be happy. I ask questions and try to understand what matters to them. I look for shared experiences (see above about motorcycling ) and share my own vulnerabilities. I provide space for them to tell me who they are 🙂.

What’s the biggest challenge around your one-on-ones?

Right now, I would say that it’s finding the time to prepare for them properly. I’ve had to do a bit of triage and spend more time focusing on my newer teammates and explicitly ask my longer-term folk to own more of that than they otherwise might. One really amazing side-effect of that, though, is that they appreciate the chance to help me out. Sharing challenges and asking for help (where appropriate, of course) is a great way to build trust and relationships.

What’s the most memorable conversation you’ve ever had in a one-on-one?

That’s really hard to come up with! Partly because some of the most memorable ones were relatively private and I’m obviously not going to violate trust and share them here.

This is not at Buffer, but I do recall one person telling me that they had applied for a role at an office of ours in another country because they wanted to move for personal/family reasons. They said that they hadn’t gotten it but that they really still wanted to move and were warning me that they were going to continue to try to move because it was the right thing for their life.

I think they were surprised when I thanked them for being honest with me and then started laying out a plan for how we could make that happen – finding other roles within our company at the same desired office location and getting them coaching on how to show their value through the interview process. I also told them I’d chat with our directors about making sure the folks hiring had access to their (excellent) work samples and internal references. I like to help.

How do you know if you’ve had a successful one-on-one?

This question has me wondering what even defines a successful one-on-one (although maybe that’s the point of it). For me personally, if someone tells me that I helped them get through a challenge, or helped them feel better about something that was bothering them, that’s successful. If they don’t explicitly tell me but they now have some tools or ideas that they feel would be useful, that’s successful. Those might be the same thing.

A really successful one-on-one is when I’ve helped someone – ideally confirmed by them letting me know that, but that’s not necessary. A good one-on-one is when we’ve had an enjoyable conversation.

(PS: I just saw this on Twitter and it sums up my feelings better than anything I said did!)

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Thanks to Kara for letting us dive into the world of remote one-on-ones at Buffer! For more company insights, check out our Q&A with Matt Himel, head of BD and Partnerships at Drop Technologies.

Use SoapBox to have amazing one-on-ones

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