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Practical ideas for better 1:1 conversations.

Short guides on agendas, follow-through, pilots, and the rhythm between managers and direct reports.

Keep your shared 1:1 doc—or switch?
October 27, 2026

Keep your shared 1:1 doc—or switch?

Check preparation, past decisions, open actions and upkeep before choosing between your shared document, existing software and 1on1.

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When your report criticises your management
October 22, 2026

When your report criticises your management

Respond to critical feedback in your 1:1, choose a change you own, and ask next time whether it helped.

Give your senior more than vague praise
October 20, 2026

Give your senior more than vague praise

Prepare specific feedback for a successful senior: one observed example, a relevant expectation and a practice to revisit together.

Talk about growth without promising a promotion
October 15, 2026

Talk about growth without promising a promotion

Keep career aspirations, verified criteria and your next information request separate, so a useful 1:1 does not imply a promotion guarantee.

A good employee has nothing to raise in your 1:1. What now?
October 13, 2026

A good employee has nothing to raise in your 1:1. What now?

Choose a useful purpose with a quiet, competent employee, offer room to prepare, and let a short 1:1 be complete without inventing a problem.

What your engineer shipped this week is not the question worth asking
August 13, 20261-on-1sengineering-management

What your engineer shipped this week is not the question worth asking

A viral HN thread argues AI flooded the visible artifact of engineering work. The question that made sense when code was the effortful part now returns a thin answer.

Know who actually wrote your next 1:1 agenda before you read it
August 11, 20261-on-1sai

Know who actually wrote your next 1:1 agenda before you read it

A meeting-notes vendor now lets its AI write into a shared agenda, not just summarize it. What matters now isn't who sees that output. It's who wrote it.

Something is already getting dropped from your week. Make sure it is not the 1:1
August 6, 20261-on-1smanagement

Something is already getting dropped from your week. Make sure it is not the 1:1

A manager's job keeps expanding while attention stays fixed, so something already gets cut every week. Adding another tool to catch it usually makes the trade-off worse, not better.

Your quietest 1:1 might be a language problem, not an engagement one
August 4, 20261-on-1smanagement

Your quietest 1:1 might be a language problem, not an engagement one

A quiet report in a second-language 1:1 might not be disengaged. The record between sessions needs to live in a language they're fluent in, not just the call.

The action item that returns to the next 1:1
July 30, 20261-on-1smanagement

The action item that returns to the next 1:1

A 1:1 commitment needs an owner, a visible state, and a place in the next session. Otherwise the meeting ends with agreement and no follow-through.

The 1:1 is the first meeting you cancel when you are busy. That is backwards.
July 28, 20261-on-1smanagement

The 1:1 is the first meeting you cancel when you are busy. That is backwards.

Nearly a third of 1:1s get canceled every week, and the busier you are the more it costs. The fix is not calendar discipline. It is where the thread lives.

When your AI talks to their AI, the 1:1 stops being a conversation
July 9, 20261-on-1sai

When your AI talks to their AI, the 1:1 stops being a conversation

AI as a drafting layer between a manager and a report outsources the reps that build the relationship. The one conversation worth keeping human is the 1:1.

Managers just lost the engagement premium. The 1:1 is what you still own
July 7, 20261-on-1sengineering-management

Managers just lost the engagement premium. The 1:1 is what you still own

Manager engagement just fell close to the level of the teams they lead. The one thing a stretched manager still fully owns is the recurring 1:1.

Who should see what the AI wrote about your 1:1, and who should not
June 25, 20261-on-1sprivacy

Who should see what the AI wrote about your 1:1, and who should not

The real question about AI in a 1:1 is not whether it belongs there. It is which output is the shared record and which is the manager's private read.

Why we built 1on1 to read prior sessions, not transcribe meetings
June 11, 20261-on-1sengineering-management

Why we built 1on1 to read prior sessions, not transcribe meetings

Most AI for 1:1s reads one meeting at a time. 1on1 reads across prior sessions, so the summary is about the relationship, not just today's transcript.

The three ways 1:1s quietly break
June 9, 20261-on-1sengineering-management

The three ways 1:1s quietly break

Most 1:1s do not collapse. They erode. Here are the three failure modes that hollow out the meeting, and how structure keeps each one from taking hold.

Pilot better 1:1s with one pair before you buy an HR suite
June 4, 20261-on-1sengineering-management

Pilot better 1:1s with one pair before you buy an HR suite

If the problem is inconsistent 1:1s, start with one manager-report pair. A narrow pilot tells you more than a broad HR-suite rollout.

Why generic 1:1 templates fail technical managers
June 2, 20261-on-1sengineering-management

Why generic 1:1 templates fail technical managers

Borrowed 1:1 templates were built for HR check-ins, so they produce status recaps and feelings questions. Here is why that fails technical managers, and what to ask instead.