1:1s Foundations: best practices for conversations that count

Psychologically-safe teams will lead to better software, delivered faster. So how can this be achieved through holding great one-on-ones?

What you learn in a 1:1 is gold. It not only helps you support your direct report, but you can use what you learn to navigate teamwork, communication, and conflict in a way that benefits your whole team. 1:1s are a critical part of a suite of tools and practices that help you grow and lead more connected, psychologically-safe teams who deliver better software to users, faster. And who doesn’t want that?

Roadmap

In this article, we’ll lay the foundation of best practices and in the follow-up,  we’ll talk about how to evaluate 1:1s: how you know they’re going well, and how you know they’re going off the rails. These two articles build on each other as this one sets the groundwork for meaningful and useful 1:1s, and the next will help you understand where and how you might need to make adjustments.

Today we’re focused on outlining those best practices for conversations that count.

Meet weekly

Why weekly? You want to keep your finger on the pulse of what’s really going on. When 1:1s are scheduled bi-weekly, and either of you have to cancel, you’ll likely be going a month between conversations and that is far too long to go without having a 1:1 with your direct report. Think of how much happens in a month. You don’t want to be that far behind!

Meeting weekly also sends a strong signal to your direct report that they matter to you. It’s a form of commitment to them. Your direct report works hard for your team, and is responsive as others set agendas and goals for them. But this is their meeting: the 45 minutes of 40 hours where they get to drive the conversation, set the agenda, and make requests. These are the 45 minutes of 40 hours that you give back.

For at least 45 minutes

Why 45 minutes? In my experience, 30 minutes is not enough time to get to the “heart” of the matter; especially when they have something sensitive to discuss, you want to make sure that you have enough time to really cover it. And once discussed, you want to make sure you both have enough time to align on action items or next steps. You want to make sure you’re making the best use of both of your time. By not leaving with a clear, shared sense of “what’s next”, you’re missing a huge opportunity.

45 minutes is good for those who are reluctant to talk for a variety of reasons. First, there’s a power dynamic. It can be hard to open up to your “boss”, especially if it hasn’t been a good experience in the past. Second, they might be wary. Think about that 15-year industry veteran who doesn’t know what it’s like to have a manager who actually cares about them. Third, you’ll need time to get to know each other. This might mean 15 minutes of conversation about who they are and what matters to them before you even get into the work stuff. Fourth, personalities won’t magically change. If they’re already shy then shyness will be present in a 1:1, so allow for some warm-up time.

Give them your full attention

Focus on your 1:1 like you would focus on writing code or doing an architecture review. Care takes focus, and your direct report deserves both.

In person, giving your full attention means putting your phone away, muting notifications, choosing a quiet room or setting where you can speak privately, and being ready to start on time.

On remote teams, there’s an extra challenge: the same screen you use for your 1:1 Zoom call is often shared with other distracting applications. Remember, you probably already have some emergency system for getting in touch with you set up (e.g. PagerDuty, phone), so it’s ok to close other “chat” tools during your 1:1. Mute your notifications, change your Slack status to “in a 1:1”, and close it.

Own it: say why 1:1s matter

It’s important for your direct report to hear you say, in your own words, why this time is important and what you hope to get out of the time together. Demonstrate ownership at the outset.

When I onboard a new direct report, I set up a separate meeting with them where I talk about my philosophy of 1:1s. I’ve been doing this with directs for over three years and I’ve found that clearly laying out my expectations for how we’ll use this time helps jumpstart the practice.

Let your direct report know that this is scheduled yet informal time for the two of you to talk meaningfully about your work together. Say that you’ll show up and be ready to listen and really hear, because showing up shows them that they matter. Explicitly invite feedback, even if it is difficult personal feedback or feedback about the practice of 1:1s.

Tell them that this is their meeting, and while you’ll be there to offer coaching and guidance about their work, you hope they’ll be able to bring items to discuss. You can get the conversation started with open-ended questions like, ‘how are you doing?’ and ‘what was hard this week?’ This signals your openness to listening while letting them lead. Open-ended questions help get you going and propel the conversation forward.

Finally, remind them that you know it feels great to talk about what’s going well and you’ll certainly celebrate wins together, but encourage them to talk openly about what’s not going well. Invite them to complain and vent when they need to. Tell them why this is a good thing: you’d honestly rather hear it directly than for someone to explode during standup, or for caustic gossip to simmer quietly behind the scenes. Let them know that you’ll be asking about what’s frustrating them at work and you hope that given a foundation of trust and safety, they’ll be able to really open up.

Conclusion

Whether you’re establishing 1:1s or seeking to improve an existing routine, I hope this first article has given you a clear sense of the foundation you can lay for meaningful conversation.

Be sure to look out for my follow-up article on LeadDev where I’ll take a deeper dive into the practice of evaluating 1:1s. How do you know they’re going well, or if you need to course correct? That and more in the next piece, so stay tuned.