Remote one-on-ones are a unique beast. Having meaningful one-on-ones with your team is hard enough when you’re in the same office. But when you’re managing remote teams, one-on-one meetings become all the more difficult. How do you really connect?

To find out, we’re speaking with Envato, a marketplace for digital assets and creative people. Envato’s headquarters is in Melbourne, Australia, but its team is most remote – even employees in the Melbourne area are encouraged to work from home whenever they like!

But with that flexibility comes additional challenges  – especially around one-on-ones. To learn more, we sat down with Lindsay Holmwood, Engineering Manager at Envato Elements, to talk about go-to questions, how he gets his team to open up and more!

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Lindsay’s 1:1 basics

• # of direct reports: 7
• Office or remote?: Remote
• Frequency: Weekly or bi-weekly
• Length: 30 minutes
• Go-to question: “And how are you really going?”

Where do you work?

I work remotely 100% of the time.

I live in the Blue Mountains just outside of Sydney, Australia. It’s about 900 kilometres from the Envato HQ in Melbourne. I also visit the office for a couple of days once a quarter for a bit of face-to-face time.

Why do you do one-on-ones?

1:1s are the most important conversations I have. 1:1s are where you have the opportunity to ask me anything. People want different things out of their one-on-ones. For some people, it’s a way to debrief or vent. Others want to ask questions. Others want to solve problems. And what people want changes over time.

My goal is to meet the needs of each individual. In our first 1:1, we’ll go through Lara Hogan’s excellent Questions for our first 1:1. One of the questions in that list is ”What makes 1:1s the most valuable for you?”

I pay a lot of attention to the answer to that question, because it sets the scene for what our 1:1s should be about.

How long are your one-on-ones?

My one-on-ones are scheduled for 30 minutes. Sometimes they run a bit longer, particularly with my direct reports who have people management responsibilities.

We will use the full time. Sometimes there will be things we need to talk about, sometimes there won’t be. Even if they don’t think we have things to talk about, we will use the time.

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

I think about preparing for 1:1s in three parts: timing, personal context and agenda.

On timing:

• I tend to Slack people 30-60 minutes before our 1:1 and ask them if the time still works for them. If not, we work out a time to reschedule.
• If so, they have a moment to think about what they want to chat about during our 1:1.

On personal context:

• I’ll bring up their answers to the “questions for our first 1:1” questions for a quick refresh.
• I’ll do a quick read of any notes I’ve taken previously during our 1:1s.

For the agenda:

• I’ll review any actions from the last 1:1 that need to be followed up.
• I’ll put cards on our shared Trello board for topics we need to discuss.
• I’ll set reminders on Slack messages if there are specific things I want to refer back to.

If I need to communicate the same message across multiple 1:1s, I’ll write up notes on what I need to say ahead of time. I’ll also adapt the message based on questions and feedback received after delivering it each time.

What does your agenda look like?

I follow a rough script every time. It looks a little like this:

1. Start with ”How are you going?” and ”What do you want to talk about today?”
2. Foreshadow if I’ve got specific topics I need to discuss. Do this as part of asking the first question: “We’ve got a few things we need to talk about today, but I wanted to start with anything important you wanted to talk about.” (These could be bigger picture topics like team changes, department changes, or broader organizational context sharing.)
3. Work through the actions and agenda items, if there are any.
4. Record actions as we go
5. Start to wrap up with “What could I be doing differently to better help you?”
6. Finish with “Is there anything else you want to chat about?”

The last question is a big contributing factor to why the 1:1s run longer than half an hour. 😂

I play fast and loose with this script – improvisation is really important when tailoring the 1:1.

Do both you and your employee add items to the agenda?

Yes! 1:1s are a two way conversation. Agenda setting is a shared responsibility.

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

When I’m following the script and I open with the “how are you going?” I’ll often follow it up with “and how are you really going?”

In Australia, social niceties dictate that the start of a conversation follows a very simple script:

1. I ask “How are you going?”
2. You respond with the only socially acceptable reply “Good, thank you.”

If you reply with anything other than “good” people look at you like you just sprouted another head. By asking how you are really going, we are breaking out of that script and getting closer to the truth of what’s really going on.

When you ask how someone is really going, you often get a surprising response – which makes for a great conversation.

Other questions I use are:

• “What’s top of mind?” which I borrowed from Sarah Atkinson of Pragmateam. It’s open, and doesn’t frame the question or response as good or bad.
• “What’s keeping you up at night?”
• ”What is going well?” and the converse ”what isn’t going well?”

"When you ask how someone is really going, you often get a surprising response – which makes for a great conversation." – @auxesis of @envato on remote one-on-one meetings Share on X

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

For me, it’s ensuring the conversation is not dominated by delivery.

Delivery is the 1:1 equivalent of talking about the weather. It’s easy to talk about, and you can fill the whole conversation with it. I have a personal preference for working on product and delivery problems. Sometimes this leaks into 1:1s (particularly if you are also motivated by delivery). I’m aware of it, but sometimes I still get blindsided by it.

That said, sometimes delivery is the most important thing we can be talking about! But it’s important to keep the amount of time we spend talking about delivery in check.

What do you do to help your employees open up?

It’s pretty simple – you ain’t gonna open up until I open up. My actions and behaviours set the boundaries for what you think is acceptable during our 1:1s. If I want you to be vulnerable, I have to be vulnerable first.

When we’re doing our first few 1:1s, you will test the waters by volunteering a little more about yourself. These opportunities are pivotal in building trust. I have to take the opportunity to mirror back the vulnerability and go even further.

Sometimes it’s talking about a health issue. Sometimes it’s talking about kids. Sometimes it’s talking about a passion outside of work. Asking questions, being curious, and taking a genuine interest are really important for building that trust.

Adam Grant’s WorkLife podcast had a great episode a few months ago called How to trust people you don’t like. It has a heap of salient tips for building trust both with people you like and people you don’t.

"My actions and behaviours set the boundaries for what you think is acceptable during our 1:1s. If I want you to be vulnerable, I have to be vulnerable first." – @auxesis of @envato Share on X

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

I know a 1:1 is successful if:

• We have learned something new about each other.
• We mark off a bunch of actions we previously committed too.
• We’ve had a difficult conversation and you walk away accepting, and ideally happy.
• We’ve talked about where you want your career to go over the next 2-3 years, and we have a clear idea about how we’re going to get you there.
• I think back to it in the next couple of days (sort of like how a good movie will keep coming back to you after you’ve watched it).
• You finish by saying “that was really productive”.

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

The most recent memorable conversation is when a people manager said they were leaving Envato to start their own sportswear business. I wasn’t surprised they were leaving (they had been with Envato for almost 5 years!), but I was surprised they were starting a business outside of tech.

These are always hard conversations to have. While they are rarely a surprise, I am always excited to hear where people are going next, and why they are heading there.

What’s the biggest one-on-one mistake that managers make?

Not doing them! Either at all, or infrequently, or unpredictably. 1:1s are your most important feedback loop to understand what is happening in your organization. If you’re not doing them regularly and predictably, you’re ignoring a really high-quality source of information about what is actually happening on the ground.

1:1s help leaders close the gap between how we imagine work is done and how it is actually done.

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Thanks to Lindsay for sharing his insights with us! For more on remote one-on-ones, check out our Q&A with Kara McNair, Engineering Manager at Buffer.

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