I have been leading people for a few years now, and if there is one thing I have changed my mind about more than anything else, it is how I run 1on1s.
I used to treat them like a status check. Twenty or thirty minutes, mostly about the work, occasionally about "how are you doing" — and then back to delivery. They were on the calendar because they were supposed to be. Most of them ended without anything memorable happening.
That is the version of a 1on1 most leaders run. And I think most reports quietly tolerate it because they assume that is just what a 1on1 is.
It is not what it should be.
What I actually want a 1on1 to do
I want the people I lead to grow. I want our time together to mean something to them — not feel like a tax they pay every other week. That sounds obvious when you write it down. It is surprisingly hard to actually do.
A good 1on1, the way I think about it now, does four things:
- Builds trust over time, conversation by conversation.
- Picks up signals — frustration, burnout, hidden conflicts — long before they turn into resignations.
- Keeps continuity. The things we agreed on last time do not quietly disappear.
- Gives the person space to talk about things they would never bring up in a team meeting.
None of those happen by accident.
The mistakes I made (most of them)
For a long time, my 1on1s failed for the same reasons I now see in almost every leader I talk to:
- No preparation. I walked in cold. I would open with "so, what is on your mind?" and let the other person carry the cognitive load. That is not partnership — that is making the conversation their job.
- No memory. I would forget what we talked about last time. The same concern came up in three meetings in a row and I treated it like new information each time. That is deeply demoralizing on the other side.
- Talking too much. When I was uncomfortable with silence, I filled it. Every time I filled it, I lost something they would have eventually said.
- Only talking about work. I used to think respecting their time meant sticking strictly to work. In reality, the most important things rarely sound like a work topic.
- Multitasking. I would half-listen while glancing at Slack. They noticed. People always notice.
If any of those feel familiar, you are not unusual. Most managers go through this. The fix is not about being a better person — it is about building a small set of habits.
Preparation is the unfair advantage
The single biggest thing that changed my 1on1s was spending a few minutes preparing before each one.
Not an hour. Not a structured prep document. Five minutes — sometimes three.
Before each meeting, I quickly review:
- What we agreed on last time, and whether I promised anything.
- Open topics I have not closed out.
- Anything I have noticed about the person since we last met — energy, tone, something they pushed back on in a team meeting.
- One real question I want to ask. Not "how is it going" — something specific.
That is it. Just enough that I walk in knowing what this conversation is for.
When you prepare like this, two things happen. First, the conversation starts somewhere useful, not from scratch. Second, the person on the other side feels seen. They feel like the meeting matters to you. That alone shifts the entire tone.
The hardest skill is listening, not noting
I used to take detailed notes during 1on1s. I was proud of them. In retrospect, they were part of the problem.
When you are typing, you are not listening. You are transcribing. You catch the words and miss the things between them — the pause before someone answers, the look when they describe a coworker, the slightly forced cheerfulness when you ask about a project.
These days, I write almost nothing during the meeting itself. Maybe a single keyword. Half a line. Then, immediately after, I take a few minutes to capture what mattered while it is still fresh.
The conversations got better. Surprisingly so.
A few open-ended questions I keep coming back to:
- "What has been the most frustrating part of the last two weeks?"
- "What would make your work feel better right now?"
- "Is there anything you have wanted to bring up but have not?"
- "If you had a free afternoon at work, what would you actually want to do with it?"
None of these are magic. They just do not have a comfortable one-word answer, which forces a real conversation.
1on1s are an early warning system
People rarely say "I am burning out." They rarely say "I am thinking about leaving." Almost no one says "I no longer see the point in any of this."
The signals show up gradually, and only if you are paying attention across multiple conversations:
- Slightly lower energy that does not bounce back.
- The same frustration coming up three times in a row.
- Less talk about future plans, more about getting through the week.
- Avoiding topics they used to engage with.
- A small "I am fine" that does not match the body language.
You cannot catch any of this in a single meeting. You catch it in the pattern. Which is exactly why continuity — actually remembering what someone told you last month — matters so much.
A 1on1 with no connection to the previous one is not really a 1on1. It is just a recurring meeting.
Light structure, not rigidity
I am not suggesting you bring an agenda to every meeting. The opposite — over-structuring kills the human part.
But a tiny bit of structure helps. I usually keep four lightweight questions in my head:
- What is still open from last time?
- How is the person doing — not just the work?
- Is there anything I want to give feedback on?
- Is there anything I promised the other person that I have not followed up on?
That is the whole "system." Enough that things do not feel random, small enough that the conversation does not turn into a checklist.
Where LeadReady fits in
I built LeadReady because I wanted to stop relying on memory and scattered notes.
It is a small app — not a productivity suite, not a CRM for your team. It is a place to keep just enough context that you can prepare for a 1on1 in a few minutes: what you talked about, what stayed unresolved, what signals you picked up. Everything stays close to you, private, built purely for 1on1s and helping your people grow.
If you already have a system that works for you, keep it. The tool is not the point. The point is that you walk into the meeting prepared, and you spend the meeting actually listening.
The thing I keep coming back to
People do not remember most of what you said in a 1on1. They remember whether they felt heard.
That is the bar. Not productivity. Not action items. Just — did they leave feeling like the person across the table actually saw them?
If yes, you are doing the most important part of leadership right.
Great 1on1s are not about talking more. They are about understanding people better.