Getting the most out of 1-on-1s

Regular 1-on-1s are to this day my favorite management tool, and it has transitioned remarkably well from working with Software Engineers to now working with other Managers. It’s probably the one constant factor in a sea of learning over the last few years, but I believe I also got a little bit better at running them. I collected something close to a Field Guide to share my current state of knowledge - This can be useful for Managers and Engineers alike because you can also use this to improve the 1-on-1 you have with your own boss.

People who follow me for a while might remember that I have been pretty hyped about 1-on-1s since the very beginning of my management days. If you speak German, I did two podcast episodes about them: The first with my personal takes and the second where I interviewed Benjamin about the same topic.

But that were the “simple” days when I was working with up to 7 direct reports. In the course of hypergrowth, I was at some point working with more than 25 direct reports, and to preserve my own sanity, but also try to be at least as useful as possible, I had to adapt and learn, so this article will be an updated version of what I knew then. Hopefully, I can write another, even better piece of content in 5 years.¹

Although I try to present a long list of technical items on how to improve 1-on-1s, it won’t be useful without one foundation: There is no substitute for caring for another human and being interested in your fellow people.²

What’s a 1-on-1?

In a nutshell, a 1-on-1 is a recurring meeting where a Manager and their direct report meet in a regular, recurring fashion. It’s one of these weird things where we collectively agreed as an industry that 1-on-1s are a good thing, so we’re all doing them. Unfortunately, we haven’t agreed on what it actually is, so everyone does something different. The topics discussed are not specified and vary greatly between managers.

For me, it is about creating trust and a safe space where topics of the individual can be discussed deeply and honestly. By building a professional relationship over time, I’m able to have the necessary candid conversations, but also hear the things I don’t want to hear. With this, my whole working relationship and my management become more effective.

Duration

I don’t think there is a universal rule, so the answer is always close to “it depends”. I prefer one hour every week with everyone. That’s a pretty big time commitment, but it allows for:

• Recency: Since it’s at max a week, everything is still fresh in memory
• Research: I can get one question/perspective from everyone within one week, which is very useful for research
• Relaxedness: If you have a whole hour, you can safely “warm up” and digress or allow side topics and chit-chat for a bit.

Once I hit a wall with too many direct reports, I chose to reduce them to 30 minutes and kept the weekly frequency. It still works, just not as good and deep as before. I haven’t experimented with 1 hour every other week yet to see if that’s any better.

Preparations and hygiene

Don’t skip

This is of course the most obvious one but notoriously neglected: Don’t skip your 1-on-1s. Sure, there is daily business going on that tries to eat your time, and sometimes it’s just not appropriate (Production is down) or possible (somebody is out sick or on vacation). In all other cases though, I strongly lean to protect my 1-on-1 time with everyone. I have politely rejected Meeting invites from VPs and other high-ranking people who were carelessly booking over my slots.

I find that once you have fought for your 1-on-1s a few times, people learn that and spend time finding other slots. So it gets easier. I usually respond on slack with something like “Sorry I can’t make this appointment as it conflicts with my 1-on-1 with $Person, and I want to show up consistently for them. Can we meet at $otherTime instead?”. Everyone has been reasonable so far.

I do all this because it sends a powerful message of You are important to me. Once you skip a lot to do other things instead, you send the message “You are not very high up my list of priorities”, and people notice that. I think on Maslow’s hierarchy of needs you mess with people on a pretty deep level.

If you want to get the most from your 1-on-1s, you need a solid foundation of trust, and showing up consistently is the base for that.

Don’t move them around all the time

A close second in terms of annoyance is moving the 1-on-1s around a lot, maybe multiple times before they happen. For people like me, who like to show up prepared to their meetings, this is a nightmare because I have to constantly stress about when it might or might not happen, and update my agenda all the time.

A special serving of hate goes out to tools like reclaim which automate this terrible behavior. My previous boss used it, and it felt like a rabbit was running through my calendar, and everything more than 4 hours out was unpredictable. So if you have a terrible meeting culture, use this to make things worse.

Here’s where I fail a lot though - I get frequently carpet-bombed with meetings that are not optional, have lots of participants, and force me to readjust my schedule on the fly. Sometimes I can fight back and protect my 1-on-1s, sometimes not. If the latter’s the case, I at least write the affected person a message explaining the why and ask for confirmation to meet at a different time on the same day. So far, people have been forgiving toward me.

Find a good time slot

In an ideal world, you would try to find a timeslot that works perfectly for both: You don’t want to interrupt anyone’s focus time. You maybe want to keep 1-on-1s batched together instead of switching between meeting types a lot. Usually, you’ll end with some compromise.

There is an ongoing idea of transferring the ownership of the calendar item from the manager to the report: This enables them to prioritize their needs better. I like the idea but haven’t done it yet as my calendar only leaves very few options anyway at the moment, so the exercise is probably futile.

Still, it helps to re-check if the slot is still a good one every few months.

Be on time

This fits the same message above: Are you important to your manager or not? Do they stand up for you (figuratively) in your previous meeting by insisting on stopping on time? Or do they de-prioritize you by just continuing the previous topic?

Of course, that doesn’t always work, but even being conscious of that, and apologizing when you mess up, goes a long way.

Share the doc

I used to have a meeting document where I kept my notes, but I kept it to myself - mostly because the structure was confusing and everything was full of embarrassing typos. As I got better with live note-keeping, and with Grammarly to help my spelling, these reasons for caution went away. I find sharing the doc with the other person very valuable now: People can add topics beforehand³, and you can both look back independently.

I try not to add things that are not fully obvious to the agenda for my reports so that they don’t have anxiety about an ambiguous point.

Running the meeting

Be present

I make a habit of closing slack and putting my Mac and Phone in “Do not disturb” mode, to avoid getting distracted for non-emergencies. Funny enough, some people who have worked with me for longer know my “Outage Face” that I make when something bad happens where you need to abandon the meeting and fix whatever is on fire. But it’s reserved for actual software outages, not when spreadsheets need input.

The same goes for the other participants - I notice when one half of one eye is still looking at the CI/CD job and the deployment pipeline. So maybe deploying something critical where you need to watch the metrics right before the meeting is not advisable either.

Avoid Status talk

A common advice, but nobody tells you how to actually do this: Naturally, Status is what’s on everybody’s mind. If you want to talk about more things, you need to have the essentials already covered:

• Be present in the daily standups (or equivalent) and be familiar with the Task board and relevant sources of information. Both should know that you know about these topics deeply enough they don’t need to be discussed.

• Small questions around work in progress can be handled async during the week

• Everyone should keep their Brag Document up to date, so that no important achievements get overlooked.

• When a meeting turns into reporting style, I try to gently steer away from it, to focus on the meta aspect of the person’s work

Bear the break

My strongest learning and something I keep struggling with: Sometimes there’s a gap in between talking, and I am naturally inclined to fill it by speaking. But if I manage to shut up, and sustain the tension - That’s where the magic happens. People sometimes need a bit of time to prepare what they want to say, and if I keep blabbering on they can’t put their thought in. Since I have learned to embrace the silence my 1-on-1s got a lot better.

Topics to wiggle in

In theory, the agenda is owned by the report, it’s their meeting. But I found value in having a few topics that I bring every now and then, just to make sure that they get covered. If you are looking for more inspiration I can recommend the Help I have a manager zine from Julia Evans

• Career Progression

How happy are you with your career progression? The work you’re doing currently? Your salary? Getting the signals early allows me to work with people on their goals, and I think contributed a lot to my high retention numbers.

• Team Health

Although I try my best to observe how my team is doing , I will never see anything. By asking, I get a lot of valuable insight about the team’s mechanics and can act proactively before anything goes haywire.

• Software Health

It helps so much to just ask: How do you feel about the state of our project? Is it healthy? What tech debt is plaguing us and stopping us from going faster? When people can share that in a safe space, they don’t just give me valuable information. It also means that their technical expertise is recognized by me.

• Question/Information of the week:

A bit selfish, but if I try to get a full picture about something in the team, I like to put it as “question of the week” in all my 1-on-1s: It’s a question I ask everyone individually, and then aggregate the answers. The same goes for very important news that I reiterate on⁴.

• My own current challenge:

A common, and very true, career advice is “Know what bothers your boss and make it go away”. But for that, my team needs to know what’s on my agenda and causing me grief. If appropriate, I share it, and sometimes I get surprised by someone picking it up and making the problem, indeed, go away.

• Feedback

Although we should strive to give each other feedback often and whenever it comes up, I find it helps me to have dedicated times where I need to aggregate feedback and think about it. So I try to fit some high-level feedback about how things are going in, to avoid any surprises during the performance evaluation cycle.

Go for a walk

When possible, I had fantastic results doing 1-on-1s in a nearby park, just walking a few circles. As a substitute, moving it to the terrace or balcony with a cup of coffee works also great, if everyone is okay with less privacy.

That’s usually better when you want to discuss one thing in-depth than a lot of different topics because you can hardly bring your notebook for notes to the park. But being somewhere different expands the thinking horizon a lot.

Afterwork

Follow up

There will be topics where you need to research something, or can’t answer it right away. I set myself a weekly calendar blocker early in the week where I review all my 1-on-1 notes, to make sure I haven’t missed any tasks that came out of last week. That has been helpful to avoid the “confused manager” stereotype, where you forget everything immediately after the meeting, and show up blank to the next one.

Keep reversing the ownership

Most of the people I work with go into these meetings with a passive mindset, but If you can find ways of reversing the ownership of the meeting, so that the reporting person drives it, it will become a lot stronger. At least for me, driving my 1-on-1 with my manager makes it a lot more useful to me. I admit I am still looking for ideas on how to turn that into reality though. If you have success there, please reach out :-)

• Hypergrowth
• People Management