I have run thousands of 1:1s over my career. Almost everyone in an organisation has one or two of them standing on their calendar, and yet very few people would say they are genuinely good at them. That gap is what I find interesting. Getting the best out of a recurring half hour with another person is a real skill, and quietly honing it has been one of the pleasures of my working life. It is also a puzzle I have never quite finished solving, which is why I wanted to write this down.
My calendar looks like a mess because of it. Every 1:1 runs a bit differently, tuned to whoever I’m sitting across from, and I’m always tweaking the format as I get to know someone better. I look forward to these conversations. There’s usually an adjustment period where neither of us has quite found the right shape for the time, and then it clicks, and after that they become some of the most valuable half hours in my week.
After enough of them, I have landed on a simple idea. Everything good about a 1:1 rests on caring about the person on the other side of the table. The rest, the agendas, the cadence, the format, is machinery built on top of that. But the machinery matters, because caring on its own does not tell you what to do with the next thirty minutes. What does is knowing which phase the relationship is in.
If everything rests on caring about the person across the table, the obvious worry is what happens with someone you did not choose and do not naturally warm to. I do not think a good manager gets to opt out of that. Caring about your team is part of the work, not a lucky accident of chemistry. A good manager can develop a real sense of appreciation for every member, find what motivates each of them, and invigorate them.
And it can start quickly. You do not need years of shared history to build a working relationship. You need aligned objectives, transparency about where you each stand, and a few principles held in common: hard work, belief in what you are doing, a willingness to be straight with each other. Get those in place early and the caring has something to grow from. It is less a feeling you wait for than a thing you cultivate on purpose.
It helps to stop judging a 1:1 session by session. The conversation where someone finally tells you they are thinking of leaving, or that a strategic project is quietly failing, looks identical on the calendar to the forgettable one before it. What you can actually read is something slower: where the relationship is, and whether the 1:1 is doing the work of that stage. A get to know you conversation in the first month is the meeting doing its job. The same conversation in month eighteen is a sign something has gone wrong.
In practice a 1:1 moves through four phases, and each one is for something different:
caring runs through all of it
│
▼
1 · GET TO KNOW (trust)
informal, no agenda
│
▼
2 · SHARE CONTEXT (momentum)
principles, challenges,
ways of working
│
▼
3 · SHARED AGENDA (structure)
items added ahead,
prioritised together
│
▼
4 · MAINTAIN (insurance)
candour, early warnings,
the itch to leave
the structure tells you
when to move: too heavy,
go forward; needed again,
go back
status and reports move
out into wider org rhythms
The first phase starts sooner than most people expect. I do not wait for a reason to book the first 1:1. The early ones are deliberately informal, no agenda, no tracking document, just getting on the same page about how we each work. It is tempting to call this unproductive. That is the point. The whole job of phase one is trust: the caring stops being a claim and becomes something the other person has evidence for. You cannot credibly care about someone you never bothered to know.
So I open on their side of the table. Something that happened, or a real question about them and how they are doing. One of my favourites is “tell me something I don’t know,” though it wears out if you lean on it, so I keep it occasional. Most of the time “how are things?” or “how have you been?” does the same work. What I am really doing is learning to read their weather: the health, the family, the good and bad months that sit behind the work and explain most of it. Get that right and, much later, they will bring you the hard things. Miss it and they never will.
At some point the conversations earn more than familiarity, and the job becomes momentum. The content shifts from the people to the work as each of us sees it: the principles we operate on, the challenges we are carrying, our preferred ways of working. If phase one produced trust, phase two produces alignment, shared context both of us can spend later without having to renegotiate it every time. Once you agree on where you are going and how you each like to travel, you can move fast together and stop relitigating the basics.
Somewhere in here, structure emerges on its own, and it is worth leaning into. The most useful form I have found is a shared document that we both keep between meetings. When something comes up that is worth the other person’s time, it goes on the list. At the start of the meeting we look at what has gathered and decide together what actually matters today, and in what order. The preparation happens before we sit down, so the time together goes to the conversation and not to working out what the conversation should be about.
This is the most deliberately structured a 1:1 gets, and that is a feature. A living agenda means nothing important waits a full week to be raised, and nothing quietly falls through the cracks between sessions. It also makes the meeting legible to both of us: we can see what we are choosing to spend the time on, and what we are choosing to let go.
For a long time I did not draw a hard line between the structured phase and what comes after it. The split was a proposal from John, a direct report of mine and a genuinely sharp one. He suggested we stop using our 1:1 to cover things that were better handled in wider forums. I was glad to agree. Once we drew that line, our 1:1s got sharper and the wider forums did their job better too, and we ended up both more efficient and more widely aligned.
That is phase four, and its real purpose is insurance. By now the operational load, status updates, reports, post mortems, has moved into our wider organisational rhythms, where it belongs and where it scales. What is left is what no other channel carries. This is where the candour you earned in phase one finally gets spent: the disagreement someone would never voice in a room, the doubt about a decision, the project that quietly worries them while it is still cheap to fix. It is where the itch to leave shows up as restlessness, long before it hardens into a resignation, if there is somewhere safe to say it. On any given week this can look like nothing happened. That is what insurance looks like most of the time. It is also the phase everything before it was building toward, a protected slot where half formed worries surface while they are still easy to act on.
There is a fashionable answer: the 1:1 belongs to the report. They set the agenda, the manager listens. I find the idea appealing, and there is something in it, but it is not how I actually run them. In my book a 1:1 is manager led, or better, coach led. I come with topics. I come with opportunities I have been turning over, especially when the results are there or the time we are spending together feels promising. I am never just a passenger.
The arrangement that has worked best sits between the two chairs: the report sets the agenda, and the manager prioritises it. The report brings the raw material of what matters to them. The manager brings the judgement of what to spend the scarce half hour on. Neither owns it alone, and the meetings I am proudest of are the ones where the question of who owns it stops having an answer, because both of us showed up with something.
Turn it around. As a report, you have more control over the phasing than you might expect, because you are usually the one bringing the agenda, and most of the resulting actions sit with you. That control comes with a responsibility: it is on you to judge honestly whether you have done the groundwork of the early phases before you push the relationship forward too fast.
Used well, your manager’s 1:1 is some of the best time you get for managing upward: setting expectations, and asking for help before you are drowning. It is also the channel whose health I would watch most closely. You do not want to arrive at a moment, well into your tenure, where you need your manager for something that genuinely matters and find the channel is not there: the 1:1 gone stale, the habit of candour never built. That capability has to exist before you need it. Keeping the manager 1:1 in good working order, even when nothing about it feels urgent, is just paying the insurance premium before you have to make a claim.
The phases do not come with dates, and the transitions are a judgement call. The most reliable signal I have is the structure itself. When the shared agenda starts to feel like overhead, when the items on it are increasingly things that could have gone somewhere else, that is the cue to lighten and move forward. When a relationship that had settled into maintenance suddenly needs the scaffolding back, that is the cue to move back. The felt weight of the structure is the instrument. Too heavy for what is actually happening, go forward. Too light, go back.
Organisational change moves the needle too, often more than anything the two people do. A management relationship can dissolve into a mentorship, and the machinery can relax. A company pivot, a role change, or a promotion can reset a settled relationship several phases back. The caring survives the reset. The context usually does not, and pretending otherwise is how good 1:1s quietly die.
That gives the failure mode a sharper name than unproductive. A bad 1:1 is usually a phase error. When one feels pointless, it is rarely the person; it is a phase mismatch, or a misread of how the other person likes to work. Running status theatre in a slot that should carry uncertainties. Forcing a prioritised agenda on someone you have not yet gotten to know. Keeping the shorthand of a settled relationship going after a reorg has quietly erased the shared context it relied on. The sessions are rarely the problem. The reading of where you are is.
It is also why the question at the top asks whether the 1:1 is worth the time, not worth the hour. Mine usually run thirty minutes, not the default hour everyone’s calendar reaches for. By the maintenance phase, cadence can loosen too. Weekly can become fortnightly, because maintenance does not need the urgency that building context did. The phase sets the format, length, frequency, structure, and the honest answer changes as the relationship does.
So, what does a 1:1 actually need to produce to be worth the time? It depends on where you are. First trust, two people who actually know how each other works. Then momentum, shared context and aligned principles you do not have to keep rebuilding. Then structure, a working agenda that keeps the important things from waiting. And finally insurance, the uncertainties and early warnings no other channel would ever have carried. Underneath all four sits the same principle: you hold 1:1s because you care about the other person. That is the one thing that makes all the rest of it worth doing.
This essay is a working draft, and I’d genuinely like it argued with. These are the questions I dropped from the essay because I could not land a strong answer on my own. Click one to drop it into the comment box and take it on, or email me. The essay will be revised as the answers come in.
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]]>My email address is andrea@dellacorte.me.
I love discussing stuff via email. Email works best for me as I’m not on social network nowadays, but sort through my mail many times a day. Additionally, writing helps me organise my mind and reshape my thinking. I promise I’ll read 100% of your emails and get back to 90%+ of your emails.
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]]>Note: This page was inspired by Kalzumeus’ Standing Invitation