coco
159 lines
10 KiB
Markdown
159 lines
10 KiB
Markdown
---
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title: "Run Excellent 1:1s"
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source: "https://x.com/dklineii/status/2048050747531518182"
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author:
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- "[[@dklineii]]"
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published: 2026-04-25
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created: 2026-04-26
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description: "This is a skills file. If it reads like the work you already do as a leader, that's because it is. The reality is you do much of this intuit..."
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tags:
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- "clippings"
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---
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This is a skills file. If it reads like the work you already do as a leader, that's because it is. The reality is you do much of this intuitively. If you have time to do it at all. But since it's a skills file, you can hand it to your LLM for help. It can help you apply the skill. Prep the meeting. Track commitments. Coach your execution. The LLM will even help you refine the skills file for you over time. It's how a chatbot becomes a Chief of Staff.
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Most managers run their 1:1s wrong. They write the agenda. They ask the questions. They take 80% of the airtime. The person sitting across from them shows up reactive, defensive, holding back things that actually matter.
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The fix is one move.
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Flip the ownership. The person owns the 1:1, not you. They come prepared with their wins, their metrics, their progress, their blockers, their lessons. You listen 90%. You speak 10%. You coach through questions, not solutions.
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When you do this every week, the rhythm accelerates. Trust compounds. Coaching compounds. Problems surface early enough to fix. You stop running 1:1 meetings. You start optimizing your operating system to help your team win.
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This file is a piece of that system. It runs weekly. Watch it grow with you.
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## The dashboard: 8 questions that show command.
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Establish the dashboard with the person when you set up your recurring 1:1. They own questions 2 through 7. They update their dashboard before the meeting and send it to you. You review it before you walk in.
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By the time you're in the room, status is already covered. Your job is to coach what the answers reveal.
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You don't go deep on all eight every week. Rotate. The structure is the scaffolding. The conversation is the work.
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**1\. How are you? (No really, how are you?)**
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Not a pleasantry. A genuine check on state. Are they energized or running on fumes? Do they have space to think, or are they spiraling?
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If the answer is real, it tells you whether to follow the rest of the dashboard or abandon it entirely. Sometimes the highest-leverage 1:1 is the one where you spend all 30 minutes on a single thing.
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**2\. What do you think we should focus on?**
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The person sets the priority. They name what's taking up oxygen. You listen first, speak second.
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Most managers skip this and jump to their agenda. Don't. The best performers already know what matters. You're confirming alignment, not assigning it.
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**3\. How are you tracking against your goals?**
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The quantitative check. On track, at risk, off track? What changed since last week?
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If they're off track, the conversation deepens naturally. They own the diagnosis before you layer in your view.
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**4\. Are there notable wins or losses to discuss?**
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The stories behind the numbers. What broke? What surprised them? What worked?
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Wins are where you see their energy spike. Lean in there. Losses are where you learn how they think about problems: do they blame the system, blame others, or own it?
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**5\. What problems are you focused on solving right now?**
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The evolution question. What are they trying to get better at? Where do they spend attention when they're not in execution mode?
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This is where development hides in plain sight.
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**6\. How are your people doing? (or: How are your key relationships?)**
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The heatmap question. If they manage, you're checking on their team. If they don't, you're asking about peers and partners.
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You're listening for who they need more from. Who they're protecting too long. Who they've stopped trying with.
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**7\. How are you getting better?**
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Growth and compounding. What did they learn last month? How are they using that insight in this month's work?
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This is where coaching gets its highest leverage. You're not teaching them something new. You're helping them see patterns in their own growth.
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**8\. What else can I do to help you succeed?**
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The catch-all. The white space. Often surfaces the thing they didn't know how to bring up.
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Leave silence after this one. Wait for the real answer.
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## The discipline: Coach through questions, not solutions.
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When they bring you a problem, the pressure is to solve it. Don't.
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The person who proposes the solution owns the implementation. The person who accepts your solution executes your judgment, not theirs. Their growth stalls. Your time fills up.
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Use these instead:
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- "What do you think you should do?" — builds their judgment
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- "What's stopping you from doing that?" — diagnoses the real blocker
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- "If you could design the ideal approach, what would it look like?" — removes constraints first
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- "What would you do if this was your company?" — flips them into ownership
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When they say "I don't know", push once: "Take 30 seconds. What's your gut saying? Not the perfect answer — the honest one."
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When you have a strong opinion they're getting wrong, share it once and stop: "I see it differently. Here's my thinking: \[your view\]. What's your reaction? Anything I'm missing?" Don't defend. Let them sit with it.
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When they bring the same problem two weeks in a row, say so: "This is the second time. What's different you need to try? What would I need to see to know you've moved it?"
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## The prep: Review their dashboard, then run the AI.
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Two inputs are sitting in front of you before the meeting: the dashboard the person filled out for this week, and your file of notes from prior 1:1s.
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**Read the dashboard first.** Their answers to questions 2 through 7 are your status update. By the time you walk in, you already know how they're tracking, what they're focused on, what's surfacing with their people, what they're learning. You don't need to ask any of it. You're free to coach.
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**Then run the AI on top of it.** The point isn't to script the meeting. The point is to surface what you'd miss reading the dashboard cold.
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Three prompts. Run in sequence.
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Prompt 1 — Pattern recognition
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Two inputs: (a) the dashboard the person filled out for this week, and (b) your notes from the last 3-4 weeks of 1:1s with them. Anonymize. Paraphrase. No real names. No company info.
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> "Role: You are an executive coach reviewing my 1:1 prep for my direct report. Here is the dashboard they filled out for this week, and my notes from the last four 1:1s. What patterns do you see? What themes are repeating? What's being said this week that connects to or contradicts what was said before? What might not be said?"
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You'll get 3-5 patterns. One or two will stand out as real. That's your prep focus.
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Prompt 2 — Prediction and listening cues
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Take the pattern that hit. Add the recent context.
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> "The pattern I'm seeing is \[pattern\]. In this week's dashboard, they wrote \[specific answer\]. Given this, what might be underneath? What should I listen for? What phrases or behaviors would tell me I'm right or wrong?"
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You'll get hypotheses plus specific phrases to listen for. "She might be questioning the role. Listen for: 'I'm not sure I'm,' 'This isn't what I thought,' 'I see other people doing X.'"
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This becomes your listening guide. Not what to ask. What to listen for.
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Prompt 3 — Calibrated questions, only if you need them
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> "Based on this pattern, here's what I want to understand: \[your ask\]. The constraint: I want them to own the diagnosis, not me to suggest answers. Give me 2-3 questions that would let them tell me what's real. Format: question / what I'm listening for / what different answers might reveal."
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You'll get 2-3 questions designed for depth, not interrogation. These are backup. If the conversation flows naturally, you don't need them.
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## The mistakes: common missteps that kill the 1:1
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Watch for these. They are how managers think they're running great 1:1s while the relationship erodes silently.
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1. **Canceling.** Nothing says what you're working on isn't important like canceling the one meeting focused on supporting you. Nothing erodes morale faster.
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2. **The manager monologue.** You take 70% of the air time. The person watches. They leave thinking the meeting was about you, not them.
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3. **Skipping question 1.** You jump straight to the dashboard and miss that someone is drowning.
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4. **Soft accountability.** You ask for commitments at the end of one meeting and never check on them at the start of the next. The team learns the meeting doesn't track. Commitments quietly become suggestions. Either confirm what they delivered AND diagnose what they didn't, or stop asking.
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5. **The interrogation.** You walk through questions 2 through 7 in the meeting because they didn't pre-fill the dashboard. The 1:1 becomes a status update again. The coaching you needed to do is now about why the prep didn't happen — start there.
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6. **Advice-giving instead of coaching.** They bring a problem. You solve it. Nothing changes because they didn't own the diagnosis.
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7. **Solving the same problem twice.** Same blocker, same advice, two weeks running. The 1:1 becomes theater.
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## A note on the skills file
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If you handed this to your LLM, here is what it does:
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- It runs Prompt 1, 2, and 3 against the dashboard and notes you give it. It surfaces the patterns. It writes the listening guide. It produces backup questions.
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- During the meeting, it can sit alongside you (think: transcript) and track which questions you covered vs. skipped. It can flag when you're talking more than 10% of the time.
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- After the meeting, it can update the running file on this person with what they said, what you noticed, what they committed to do this week, and what to listen for next time.
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Over time, as you tell it which patterns were right and which were wrong, it tailors itself to you. The moves you rely on. The signals you react to. The way each direct report responds when you ask the question that matters.
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That is how you transform a chatbot into your Chief of Staff.
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We're helping 50 leaders do this at scale next week in our [MGMT Second Brain workshop](https://maven.com/dave-kline/build-your-management-second-brain-the-ai-that-gets-smarter-as-you-lead). Join us for this 3-hour hands-on build session! |