gtm-operating-cadence

SKILL.md

Operating Cadence

The meeting structure that worked at 30 people collapses at 100. What worked at 100 collapses at 300. The failure mode is always the same: too many people in too many meetings making too few decisions.

When to Use

Triggers:

"Our meetings don't produce decisions"

"We're growing but alignment is getting worse"

"How often should we meet?"

"Nobody knows what's happening across functions"

"Decisions take forever"

"Leadership is in meetings all day"

Context:

Companies scaling from 20 to 300+ people

Post-PMF through growth stage

Distributed / remote teams

Any stage where "we need to talk about this" has become the default

Core Frameworks

1. The Five-Level Meeting Architecture

The Pattern:

Different meetings serve different purposes. Conflating them creates either inefficiency (too much time) or confusion (unclear decisions). Separate meetings by function, frequency, and decision authority.

Level 1: Daily Standup (15 min, teams only)

What we finished yesterday, what we're starting today, what's blocking us

5-10 people max. Whole-company standups are theater

Anti-pattern: Status reporting (use Slack, not meetings)

Anti-pattern: Strategic discussion (wrong time, wrong place)

Success criteria: Finishes in 15 minutes, surfaces 1-2 blockers

Level 2: Weekly Functional Reviews (60 min, function leadership)

Each function gets its own weekly rhythm:

Product team Friday 4pm: metrics, user feedback, roadmap blockers

GTM team Tuesday 4pm: pipeline, customer updates, deal health

Engineering Wednesday 4pm: velocity, bug backlog, deployment

Format: Metric recap (10 min) → Wins/blockers (15 min) → One deep-dive (30 min) → Next week priorities (5 min)

Anti-pattern: Trying to solve every problem in the meeting. Pick 1-2, delegate the rest to follow-ups.

Level 3: Weekly All-Hands (60 min, whole company)

The single most important alignment mechanism at a scaling company.

CEO update (15 min): north star progress, week focus, what's changed

Metric dashboard (10 min): same format every week (consistency enables pattern recognition)

Deep dive (20 min): one strategic topic needing team input — not a presentation, a discussion

Q&A (15 min): real questions, real answers

Anti-pattern: Defensive tone. All-hands should be straightforward, not spin.
Anti-pattern: Inconsistent metrics. If you change the dashboard, the team can't track progress.

Level 4: Bi-Weekly Leadership Alignment (90 min)

North star progress (5 min)

Functional updates (30 min, 5-7 min each)

Major decisions needing resolution (30-40 min): resource conflicts, strategic pivots, customer/product decisions

Next 2 weeks planning (15 min)

This is where cross-functional blockers get resolved. If functions operate independently, this meeting isn't working.

Level 5: Quarterly Strategic Planning (half-day to full-day)

Previous quarter retrospective (90 min): What worked, what didn't, what we'd do differently

Next quarter planning (120 min): What are we optimizing for? What's the roadmap?

Function breakouts (90 min): Each function plans their quarter

Synthesis (60 min): Functions share commitments, resolve conflicts

Anti-pattern: Too much "fun activity," not enough substance.
Anti-pattern: No clear decisions coming out.

Scaling Adjustments:

<30 people: Levels 2-3 only. Skip daily standups (you see everything). Skip bi-weekly leadership (you ARE leadership).

30-100 people: Add all 5 levels. Monthly review catches what you no longer see daily.

100-300 people: Add skip-level reviews. You're 2+ layers from execution.

300+ people: Add function-specific sub-cadences. CEO should be in fewer meetings than at 50 — not more.

The Rule That Makes This Work:

Every meeting must produce decisions or be cancelled. Status updates are async. If you're in a meeting and nobody is making a decision, leave.

2. Weekly Metric Reporting (The Dashboard That Catches Problems Early)

The Pattern:

Monthly reporting catches problems 30 days late. By then, a bad month is baked. Weekly reporting catches problems in week 2, when you can still save the month.

The Format (Same Structure Every Week):

WEEK OF [DATE]

North Star: [Metric]
This Week: [Value] | Last Week: [Value] | Change: [+/-] [↑↓]
Context: [One sentence — why this trend matters]

Functional Metrics:
  Product:  7-Day Retention: 34% | Last: 33% | +1% ↑
            Feature Adoption: 18% | Last: 16% | +2% ↑
            Context: Onboarding improvements showing impact

  GTM:      Pipeline: $8.2M | Last: $7.8M | +$400K ↑
            New POCs: 3 | Last: 2
            Context: Partner pipeline adding deals

  Health:   Team Morale: 7.2/10 (down from 7.5)
            Context: Org restructure causing uncertainty

The Discipline Rules:

Same metrics every week. Consistency enables pattern recognition. OK to add metrics, never drop them.

One context sentence per metric. Not just the number — why does this matter? Vs plan? Vs last period?

Trend direction for every metric. Up/down/flat arrow. If it moved significantly: temporary or structural?

Traffic light colors. GREEN (on track), YELLOW (watch), RED (action needed). Every RED item must have: owner, specific action, deadline.

The Escalation Rule:

If a metric is RED two weeks in a row with the same action plan, escalate — the action plan isn't working.

How Many Metrics:

Pick 8-12 total. If a metric doesn't change your behavior when it moves, remove it. Dashboards with 40 metrics are decoration, not decision tools.

Common Mistake:

Vanity metrics that look good but don't predict business outcomes. Total downloads without adoption context. CEO headlines without supporting metrics.

3. Quarterly Planning (The Process That Prevents Strategic Drift)

The Pattern:

Without quarterly planning, companies drift. Each function optimizes locally. Sales chases deals outside ICP. Product builds features for one customer. Marketing runs campaigns that don't connect to pipeline.

The 3-Week Planning Cycle:

Week 1: Retrospective + Data Gathering

Previous quarter results vs plan (leadership prepares)

Each function writes 1-page retrospective: what worked, what didn't, what we'd do differently

Finance prepares: revenue actuals, spend actuals, forecast

Market data: competitive moves, customer feedback themes, win/loss analysis

Week 2: Priority Setting (Leadership Half-Day)

Review retrospectives (30 min — pre-read, don't present)

Agree on 3-5 company-level priorities

For each: owner, success metric, resource requirements

Identify what you're not doing (as important as what you are)

Resolve cross-functional dependencies

Use the north star as tiebreaker: "Does this help us hit the goal? Prioritize. Nice-to-have? Defer."

Week 3: OKR Cascade + Resource Allocation

Each function translates company priorities into team OKRs

Leadership reviews for alignment

Resource allocation finalized (headcount, budget, tools)

Final plan shared company-wide

The Quarterly Commitment Format:

Q2 2026 Roadmap
North Star: [What we're optimizing for]

Pillar 1: Product (25% team effort)
  Initiative: [Name]
    Problem: [What we're solving]
    Success: [Specific metric]
    Owner: [Name]
    Timeline: [When]

Pillar 2: GTM (50% team effort)
  Initiative: [Name]
    ...

Pillar 3: People (10% effort)
  Initiative: [Name]
    ...

Pillar 4: Tech Debt (15% effort)
  Initiative: [Name]
    ...

The "Not Doing" List:

For every priority you add, identify one thing you're stopping. If you can't name what you're not doing, you have too many priorities.

Common Mistake:

Quarterly planning that produces a 30-page doc nobody reads. The output should be: 3-5 priorities on one page, each with owner and metric. That's it.

4. Decision Velocity and Authority

The Pattern:

At 20 people, the CEO makes every decision in real-time. Fast. At 100 people, decisions require alignment. Slow. At 300, decisions require alignment, approval, and documentation. Glacial.

The fix isn't more meetings. It's clear decision rights.

Decision Authority Matrix:

Decision
Who Decides
Timeline
Escalation

Company strategy
CEO
1 week
Board if strategic

Feature priority
Product lead
1 week
CEO if >3 eng weeks

Customer support issue
CSM
Immediately
CS lead if escalated

Marketing campaign
Marketing lead
2 weeks
CMO if >$10K budget

Hiring
Function leader
2 weeks
CEO if role not approved

New partnership
CEO
2 weeks
Board if strategic

Vendor selection
Function leader
1 week
CEO if >$50K/year

The Problem:

Scaling companies start treating reversible, low-stakes decisions like irreversible, high-stakes ones. Everything needs approval. Everything needs a meeting. Everything needs consensus.

The Fix:

Type 1 (Irreversible, high-stakes): Pricing model, market entry, major partnership → CEO/leadership decides with debate in one meeting. Timeline: 1-2 weeks max.

Type 2 (Reversible, low-stakes): Campaign creative, feature prioritization, single hire → Function owner decides, informs, iterates. Timeline: same day or next day.

Make decisions with 70% information, not 100%. Speed is a competitive advantage at every stage.

Common Mistake:

Consensus culture masquerading as collaboration. "Let's get everyone aligned" often means "nobody wants to decide." Name the decider. Let them decide. Move on.

5. Async-First Communication

The Pattern:

Synchronous meetings don't scale. Default to async, escalate to sync.

Async First (No Meeting Needed):

Decision documents (even major ones — write up proposal, solicit comments, 48-72 hours for feedback, decide if consensus or no material objections)

Progress updates (use weekly reporting, not meetings)

Process changes and SOPs

Decisions already made (inform, don't discuss)

Sync When:

Real-time brainstorming needed

Major disagreement to work through

Complex topic needing whiteboard

Team building / relationship

Documentation Discipline:

Every decision documented: What was decided? Why? Who decided? When does it take effect? Who needs to know?

Store in searchable format (wiki, shared drive). New hires onboard faster. Past decisions don't get relitigated.

Common Mistake:

"Quick sync" meetings that grow to consume 10 hours per week. Over-communicating in Slack (ephemeral, noisy) and under-communicating in persistent formats (docs, emails). The important stuff should be searchable 6 months later.

6. The CEO Weekly Update

The Pattern:

The single highest-leverage communication tool at a scaling company. 5-10 minutes to write. Everyone reads it. It sets context, celebrates wins, names priorities, and creates shared understanding.

Format (Sent Sunday Night or Monday Morning):

1. Week Focus (1 paragraph):
What's the priority this week? What should the team be focused on?

2. North Star Progress (1-2 bullets):
Where are we on the key metric? Trend up/down/flat? Why does this matter?

3. Wins This Week (3-5 bullets):
What shipped? Customer/partner wins? Big picture implication?

4. Blockers Getting Resolved (1-2 bullets):
What are we unblocking this week? Who needs to know?

5. Ask (1 bullet, optional):
What help does the team need? Referrals, feedback, customer introductions?

The Rule:

Same day every week. Consistency signals operational discipline. If you skip a week, the team notices — and starts wondering what you're not telling them.

Common Mistake:

Too long (team doesn't read), too detailed (save that for function meetings), only good news (team loses trust), inconsistent (team stops reading).

7. Role Clarity > Titles

The Pattern:

The most powerful tool for speed isn't hierarchy — it's explicit role clarity. When someone knows exactly what they own and can't delegate it away, decisions happen faster.

How to Execute:

Every initiative gets exactly one owner (with supporting teammates)

Metrics are tied to that owner

Success is measured by moving KPIs, not completing tasks

Eliminate initiatives without clear ownership within 48 hours

The Test:

Can you name the single person who owns this outcome? Not "the team" — a person. If you can't, the initiative will drift.

Common Mistake:

Assigning projects to multiple people ("everyone owns it" = nobody owns it). Measuring activity instead of impact. Burn rate going up without clear ROI tracking per initiative.

Decision Trees

Which Meeting Levels Do We Need?

Company size <30?
├─ Yes → Levels 2-3 only (weekly functional + all-hands)
└─ No → Continue...
    │
    30-100 people?
    ├─ Yes → All 5 levels
    └─ No → All 5 + skip-level reviews + function sub-cadences

Is This Meeting Worth Keeping?

Does it produce decisions?
├─ No → Can it be async?
│   ├─ Yes → Make it async, cancel the meeting
│   └─ No → Redesign with decision agenda
└─ Yes → Are the right people in the room?
    ├─ No → Fix attendee list (fewer > more)
    └─ Yes → Keep it

Common Mistakes

1. Adding meetings as you grow
Replace them. At 200 people, the CEO should be in fewer meetings than at 50.

2. Status update meetings
If it can be an email, it should be an email. Meetings are for decisions.

3. Changing metrics every quarter
Consistency enables trend identification. Same dashboard, every time.

4. Consensus culture
Name the decider. Let them decide. Inform everyone else.

5. All information in Slack
Ephemeral, noisy, unsearchable. Important decisions go in docs.

6. Quarterly planning that produces 30-page docs
3-5 priorities on one page. That's the output.

Quick Reference

Meeting architecture:
Daily standup (15 min) → Weekly functional (60 min) → Weekly all-hands (60 min) → Bi-weekly leadership (90 min) → Quarterly planning (half-day)

Weekly metric dashboard:
8-12 metrics, same format every week, traffic light colors, one context sentence per metric, owner + action + deadline for every RED

Quarterly planning cycle:
Week 1: Retro + data → Week 2: Priority setting (3-5 max) → Week 3: OKR cascade + resources

Decision authority:
Type 1 (irreversible): CEO/leadership, 1-2 weeks → Type 2 (reversible): Function owner, same day

CEO weekly update:
Week focus → North star progress → Wins → Blockers → Ask

Information flow:
Daily: Slack wins/customer-voice → Weekly: CEO email + function updates → Monthly: All-hands + skip-levels → Quarterly: Planning share + demos

Related Skills

enterprise-account-planning: Stakeholder management and deal cadence patterns

0-to-1-launch: Launch-specific execution cadence

board-and-investor-communication: Board meeting structure and investor updates

Based on operating cadence design across companies scaling from 20 to 1,000+ employees, including the five-level meeting architecture that survived 3x headcount growth, the weekly reporting format that caught pipeline problems 3 weeks earlier than monthly reviews, and the CEO weekly update format refined across multiple companies. Not theory — patterns from building operating systems through hypergrowth and teaching them to the next team.