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What Does a 1:1 Actually Need to Produce to Be Worth the Time?

Tags: work • management • meetings

This is a work in progress, published early on purpose — co-written with Claude (I supply the opinions and the corrections; it does most of the typing). See Request for comments at the end.

Every recurring meeting eventually gets audited. Someone looks at the calendar, multiplies the headcount by the hour, and asks what the company is buying. Standups survive the audit because they produce coordination. Planning meetings survive because they produce decisions. The 1:1 is the meeting that struggles to answer — ask a manager what last week’s 1:1s produced and you mostly get abstractions: alignment, connection, trust. Ask the report and you sometimes get worse: “we did status.”

That’s the trap in the question, though. “What did it produce?” treats a 1:1 like a factory and judges it session by session — and at that resolution the signal isn’t there. The session where someone finally tells you they’re 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 judge 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 symptom.

Start from why you hold them at all. I do 1:1s because I care about the person on the other side of the table — less a technique than a principle. Everything else, the agendas and cadences and formats, is machinery layered on top. If the caring isn’t there, no format rescues the meeting; people can tell when the hour is an audit wearing a friendly face. If it is there, the 1:1 is where it becomes visible and usable — the place where the other person learns, through repetition, that bringing you a half-formed worry is safe and worth their while.

Ben Kuhn’s “The unreasonable effectiveness of one-on-ones” — the essay I think of whenever 1:1s come up — reaches this from the opposite end. The detail that stays with me: he ran weekly 1:1s with his partner, a philosophy grad student, who credits them with speeding up her dissertation by a year. No agenda machinery, no organizational rhythms — none of it was needed, because the caring and the shared context were already there, years deep. That’s the limiting case: when you start with what matters, a 1:1 needs almost no structure at all. A manager and a new report start with neither. Most of what I do with 1:1s is, one way or another, machinery for building what Kuhn got for free.

In practice that machinery has three phases:

caring ─────────────────────────────────────────────────────────▶

┌────────────────┐     ┌─────────────────┐     ┌────────────────┐
│ 1 · GET TO     │────▶│ 2 · SHARE       │────▶│ 3 · MAINTAIN   │
│     KNOW       │     │     CONTEXT     │     │                │
│                │     │                 │     │                │
│ informal, no   │     │ agenda arrives; │     │ uncertainties, │
│ agenda; how    │     │ principles ·    │     │ personal       │
│ we each work   │     │ challenges ·    │     │ challenges     │
│                │     │ ways of working │     │                │
└────────────────┘     └─────────────────┘     └───────┬────────┘
                                ▲                      │
                                │  pivot · role change │
                                │  · promotion (reset) │
                                └──────────────────────┘

status · reports · post-mortems ────▶ organizational rhythms

The first phase starts sooner than most people expect: I don’t 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’s tempting to call this unproductive; that’s the point. The entire product of phase one is that the caring stops being a claim and becomes something the other person has evidence for. You can’t credibly care about someone you never bothered to know.

At some point the conversations earn an agenda. That’s phase two: a deliberate investment in structure — a shared list, prioritized, so the time goes to what matters most. The content shifts from the people to the work as each of us sees it: the principles we operate on, the challenges we’re carrying, our preferred ways of working. If phase one produced familiarity, phase two produces alignment — shared context both of you will spend later without having to renegotiate it.

Phase three is maintenance, and it’s the one the calendar auditor squints at. By now I’ve collated the operational load — status updates, reports, post-mortems — into organizational rhythms, where it belongs and where it scales. What’s left is what no other channel carries: I encourage the other person to bring mostly their uncertainties and personal challenges. On any given week this can look like nothing happened. It’s also the phase everything before it was building toward: a protected slot where half-formed worries surface while they’re still cheap to act on.

The phases don’t come with dates. Transitions are a judgement call, managed naturally — forcing them defeats the purpose. And they move in both directions. Organizational change can push a relationship forward: a management position dissolves into a mentorship, and the machinery can relax. It can also push one back: a company pivot, a role change, a promotion can reset a phase-three relationship to phase two. The caring survives the reset; the context doesn’t — and pretending otherwise is how good 1:1s quietly die.

Which gives the failure mode a sharper name than “unproductive”. A bad 1:1 is usually a phase error: running status theatre in a slot that should carry uncertainties; forcing a prioritized agenda on someone you haven’t yet gotten to know; keeping the phase-three shorthand going after a reorg has erased the shared context it relied on. The sessions are rarely the problem. The reading of where you are is.

It’s also why the question at the top asks whether the 1:1 is worth the time, not worth the hour. A fixed weekly hour is the calendar’s answer to a relationship question. The phase should set the format — how long, how often, how structured — and the honest answer will change 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. Early on, two people who actually know how each other works. In the middle, shared context and aligned principles. Later, the uncertainties no other channel would have carried. Underneath all three sits the same principle — the one I took from Kuhn’s essay even after discounting most of its particulars: you hold 1:1s because you care about the other person. That’s the one product no audit will ever find on a calendar, and the only one that makes the others possible.

Request for comments

This essay is published as a working draft, and I’d genuinely like it argued with. Questions I’m still chewing on:

• Does the phase arc apply beyond manager–report — to peers, or to your own manager?
• Transitions are judgement calls, but if I had to explain the judgement: what are the observable signals that a phase is done?
• What does the reset conversation actually sound like after a pivot or a promotion?
• Should duration and cadence follow the phase explicitly — and how?

Comments are open below, or email me. The essay will be revised as the answers come in.