The secret sauce to 1:1 meetings (make every session a win-win)

A 1:1 is not a recurring calendar event.

In your first 90 days, it’s your main alignment mechanism with the person who influences:

• what “good” looks like
• what gets prioritized
• what gets forgiven

Treat it like a strategy meeting, not a vibe check.

What a good 1:1 prevents

The most expensive phrase in early career is:

“Oh — I thought you knew.”

If your manager learns something important late (a slipping date, a blocked dependency, a stakeholder unhappy), it’s rarely because you’re incompetent.

It’s usually because you didn’t have a reliable place to surface:

• risks
• decisions
• tradeoffs

That reliable place is the 1:1.

What prompted this

The internet is full of “1:1s are pointless” takes — and the comments get spicy because everyone is talking past each other. Most people aren’t having 1:1s; they’re having awkward weekly chats. Two useful anchors: Rands’ “The Update, The Vent, and The Disaster” (https://randsinrepose.com/archives/the-update-the-vent-and-the-disaster/) and Ask a Manager on common one-on-one mistakes (https://www.askamanager.org/2014/10/youre-making-4-mistakes-in-your-one-on-ones-with-your-team.html).

The mindset: this is your meeting

You’re not “waiting to be managed.”

You’re practicing managing up.

That means:

• you bring the agenda
• you bring the decisions you need
• you leave with next steps

A strong 1:1 produces at least one of these outcomes:

• a decision
• a priority
• a cleared blocker
• a clearer quality bar (“this is what great looks like”)

If you leave with none of those, the meeting is slowly turning into a recurring coffee chat.

Phase 1: before the meeting (5 minutes that makes you look senior)

Use a running doc and keep the newest week at the top.

Put your questions first.

A simple agenda

• Wins
• Status (3 bullets)
• Blockers + decisions
• Priorities for next week
• Calibration / growth

Wins (yes, even small ones)

This is not ego. It’s signal.

Examples:

• “Shipped ___.”
• “Unblocked ___.”
• “Closed the loop with ___.”

Status in 3 bullets

• Shipped:
• Next:
• Risk:

If you can’t do it in 3 bullets, it’s not a status update — it’s a story.

A running 1:1 doc template (copy/paste)

Use one doc and keep the newest week on top:

# 1:1 — [Your Name] + [Manager]

## This week (top priorities)
-

## Wins
-

## Status (3 bullets)
- Shipped:
- Next:
- Risk:

## Decisions / Questions (manager input needed)
1)

## Blockers
-

## Feedback / Calibration
-

## Action items
- [Me] ___ by ___
- [Manager] ___ by ___

Phase 2: during the meeting (structure beats vibes)

Start positive (2 minutes)

Open with one win and one sentence of context.

Script:

“Quick win: ___. It matters because ___.”

Bring blockers with options (don’t dump problems)

Don’t bring:

• “I’m stuck… what should I do?”

Bring:

• “Here are the options. Here’s what I recommend. Any objections?”

Scripts:

A/B choice

“We can do A or B. I recommend A because ___. Are you aligned?”

Priority check

“Given my capacity, what’s the correct order: X then Y, or Y then X?”

Unblock request

“I’m blocked on ___. Can you connect me with ___ or approve ___ so I can move?”

Use your manager for judgment (not trivia)

Your manager’s real value is not answering every question.

It’s priority + judgment.

If you’re overloaded, say it clearly:

“I can do two of these three this week. Which two should win?”

Phase 3: after the meeting (follow-through is the whole game)

Send a short recap. Same day.

Template:

“Recap:

• Decisions: ___
• Me: ___ by ___
• You: ___ by ___”

This single habit creates:

• a paper trail
• fewer misunderstandings
• faster execution

Common 1:1 problems (and quick fixes)

“I don’t have anything to talk about”

You do.

Bring one of these:

• “What does ‘great’ look like for my work this week?”
• “What’s the biggest risk to the plan right now?”
• “Is there anything you want me to change about my updates?”

“My manager hijacks the meeting”

It happens.

Open with your two most important asks:

“Before we jump into updates, I have two decisions I need today so I can keep moving.”

“I leave with ‘I’ll think about it’”

Ask for the decision:

“To confirm, are we choosing A? If so, I’ll proceed today.”

Depending on where you sit:

• Early-career: the win is not “talk a lot.” The win is “leave with one decision and one next step.”
• Manager: coaching the format isn’t micromanagement — it’s alignment. Tell people your defaults (“3-bullet status + one decision”).

Edge cases

• If your manager is a chronic canceler, the running doc becomes the meeting. Keep it updated and ask for async answers.
• If your org already has strict 1:1 expectations, use this as your internal structure even if you don’t control the meeting.

Next step

Create the running doc today and add your top two decisions/questions for next week.

Want a ready-made structure? Use the Manager 1:1 agenda.