Liqiongyu Lenny Skills Plus Running Effective 1 1s

Running Effective 1:1s

Scope

Covers

• Designing a lightweight 1:1 operating system (purpose, cadence, meeting types, shared docs)
• Running 1:1s as coaching conversations (not just status updates)
• Holding career development conversations (life story → future dreams → action plan)
• Doing basic wellbeing/recovery check-ins (joy/energy) without crossing into therapy/medical advice
• Running skip-levels and special sessions (e.g., post-crisis “make them feel heard” 1:1s)

When to use

• “My 1:1s are turning into status updates—help me redesign them.”
• “Create a 1:1 agenda + shared doc template for me and my direct reports.”
• “I’m a new manager—set up my 1:1 cadence and question bank.”
• “Help me run better career conversations in 1:1s.”
• “Plan a skip-level program and templates.”

When NOT to use

• You need HR/legal guidance, an investigation, or a performance improvement plan (involve HR/legal; use your company process)
• You need a project status meeting cadence (use team/ops rituals; 1:1s should not be the primary status channel)
• The situation involves immediate safety/mental health crisis (seek professional help and follow company policy)
• You want to develop a PM's product skills through structured coaching (use coaching-pms)
• You need to design team-wide meetings, standups, or group rituals (use running-effective-meetings)
• You want to delegate work effectively and track outcomes (use delegating-work)
• You want to manage your relationship upward with your own boss (use managing-up)

Inputs

Minimum required

• Your role and context (manager level, org type, function, time zones)
• Who the 1:1s are for (directs, skip-levels) and relationship stage (new, stable, strained)
• Current 1:1 cadence and what’s not working (2–5 concrete examples)
• What you want to change (coaching, feedback, career growth, wellbeing, alignment, retention)
• Constraints: meeting load, confidentiality/PII rules, any HR policies, time box/deadline

Missing-info strategy

• Ask up to 5 questions from references/INTAKE.md (3–5 at a time).
• If key details are missing, proceed with a default 1:1 operating system and clearly label assumptions.
• Do not request secrets or sensitive personal data; use anonymized summaries.

Outputs (deliverables)

Produce a 1:1 Operating System Pack in Markdown (in-chat; or as files if requested):

1. Context + goals (what 1:1s are for in this team; what they are not for)
2. Cadence + meeting types plan (weekly/biweekly + barbell approach + skip-level cadence)
3. Shared 1:1 doc templates (agenda, notes, action items, topics backlog)
4. Coaching toolkit (conversation rules + question bank + “coach vs advisor” prompts)
5. Career development conversation plan (life story → dreams → action plan, with templates)
6. Wellbeing/recovery check-in pattern (joy/energy prompts + boundaries + escalation guidance)
7. Special-situation playbooks (post-crisis listening session; urgent topical meeting; skip-level template)
8. Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md
Expanded guidance: references/WORKFLOW.md

Workflow (8 steps)

1) Intake + boundaries + safety

• Inputs: user context; references/INTAKE.md.
• Actions: Confirm goals for 1:1s, current failure modes, constraints, and any HR/safety boundaries. Decide which deliverables are needed (full pack vs just templates).
• Outputs: Context snapshot + assumptions/unknowns list.
• Checks: The purpose of 1:1s is explicit and does not conflict with HR/legal policy.

2) Define the 1:1 purpose and “what goes where”

• Inputs: goals + failure modes.
• Actions: Separate topics into channels: team status rituals vs 1:1 coaching, career, feedback, and blockers. Define what the 1:1 should consistently cover (and what it should not).
• Outputs: “What goes where” map + 1:1 purpose statement.
• Checks: Status updates have a non-1:1 home (async or team ritual).

3) Choose cadence + meeting types (barbell design)

• Inputs: roster, seniority, relationship needs, time budget.
• Actions: Propose a cadence plan: standing 1:1s where they add value, plus a barbell approach (high-quality relationship catch-ups + urgent topical meetings). Add a skip-level cadence if needed.
• Outputs: Cadence + meeting types plan.
• Checks: The plan reduces meeting bloat while improving timeliness and relationship quality.

4) Create the shared 1:1 documentation system

• Inputs: tools available (doc, notes, tracker), privacy constraints.
• Actions: Define a shared doc per report (or per relationship) with: agenda, running topics backlog, notes, decisions, and action items. Include a pre-work expectation for both sides.
• Outputs: Shared 1:1 doc template + action item tracker conventions.
• Checks: Every meeting ends with written next steps and owners; sensitive content is handled appropriately.

5) Shift from “advisor” to “coach” (conversation rules)

• Inputs: common problem types brought to 1:1s.
• Actions: Write a coaching toolkit: default questions, how to avoid jumping to answers, and how to help the report reason through tradeoffs. Include a “when to be directive” exception list (risk, safety, time-critical).
• Outputs: Coaching rules + question bank.
• Checks: The toolkit trains independent problem solving rather than escalating everything to the manager.

6) Build a career development sequence (3 conversations)

• Inputs: role expectations, growth paths, aspirations (if known).
• Actions: Create a career plan that schedules three deeper conversations: Life Story, Future Dreams, Career Action Plan. Define how tactical 1:1s connect to growth over time.
• Outputs: Career conversation plan + templates.
• Checks: The plan results in 1–3 concrete growth bets and follow-up checkpoints.

7) Add wellbeing/recovery + special situations

• Inputs: team stress level, recent change events, relationship health.
• Actions: Add a lightweight joy/energy check-in pattern and a “behavioral activations” list. Add special playbooks: post-crisis listening session (feel heard), urgent topical meeting, and skip-level structure.
• Outputs: Wellbeing pattern + special-situation playbooks + templates.
• Checks: Boundaries are clear (not therapy); escalation paths are documented.

8) Quality gate + rollout plan

• Inputs: full draft pack.
• Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add Risks / Open questions / Next steps. Propose a 2–4 week pilot with review prompts.
• Outputs: Final 1:1 Operating System Pack.
• Checks: Pack is immediately usable; responsibilities and follow-ups are explicit.

Quality gate (required)

• Use references/CHECKLISTS.md and references/RUBRIC.md.
• Always include: Risks, Open questions, Next steps.

Examples

Example 1 (new manager): “I’m a new product lead with 6 direct reports across time zones. Design my 1:1 cadence, a shared 1:1 doc template, and a coaching question bank. Include a career conversation plan and a 4-week pilot.”
Expected: cadence plan + templates + coaching toolkit + career sequence + quality gates.

Example 2 (meeting bloat): “My calendar is overloaded with weekly 1:1s. I still want strong relationships and fast escalation on urgent topics. Propose a barbell approach, updated agendas, and a skip-level cadence.”
Expected: reduced standing roster with explicit alternatives; relationship catch-ups + urgent topical meetings; skip-level template.

Boundary example: “I need to document poor performance and start a PIP.” Response: recommend HR/performance management process; offer to help create a feedback conversation plan and expectations doc, but not to run an HR process via 1:1 templates.

Boundary example 2: “Help me coach my PM on prioritization frameworks and product sense.” Response: PM-specific skill development is better served by coaching-pms. This skill designs the 1:1 operating system (cadence, templates, coaching questions), not the content of PM coaching programs.

Anti-patterns (common failure modes)

1. Status update 1:1s: Spending the entire 1:1 on project updates that could be async. The “what goes where” map must move status out of 1:1s into team rituals or written updates.
2. Manager monologue: The manager talks 80% of the time, giving advice and direction. Effective 1:1s are coaching-first, with the report driving the agenda and the manager asking questions.
3. No shared doc or follow-through: Running 1:1s with no written agenda, notes, or action items. Decisions and commitments evaporate between meetings; the same issues recur.
4. Career conversations never happen: Filling every 1:1 with tactical topics and never scheduling the deeper life story/dreams/action plan conversations. Career development requires dedicated time, not leftover minutes.
5. One-size-fits-all cadence: Running weekly 30-minute 1:1s with every report regardless of seniority, relationship stage, or need. Cadence should be tailored; a barbell approach (relationship catch-ups + urgent topical meetings) often works better.

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