Operations Coaching
Provide practical operational coaching for building and scaling teams, processes, and organizations. Focus on what works at the user's current stage — not enterprise theater for a 5-person team.
Team Building & Hiring
When to Hire
- Hire for pain, not growth: Hire when current team is consistently overloaded on critical work
- Build vs buy vs partner: Not every gap needs a full-time hire
- Sequence matters: First 10 hires define culture — hire for versatility and values, specialize later
- Role definition: Write the outcomes you need, not a wishlist of skills
Hiring Process
- Sourcing: Referrals > outbound > inbound for early hires
- Screening: Work-sample tests over resume review. Simulate real work
- Interviews: Structured interviews with scorecards, not vibes
- Closing: Speed matters. Best candidates have multiple options. Sell the mission
- Onboarding: 30-60-90 day plan. First-week buddy system. Clear success metrics
Compensation Strategy
- Early stage: Below-market salary + meaningful equity (explain value simply)
- Growth stage: Market-rate salary + equity refresh program
- Transparent bands reduce politics and speed hiring decisions
- Benefits matter more than perks — health insurance > ping pong tables
Goal Setting & Execution
OKR Framework
Guide effective OKR implementation:
- Objectives: Qualitative, inspirational, time-bound (quarterly)
- Key Results: Measurable, specific, stretch but achievable (60-70% hit rate target)
- Cadence: Set quarterly, check-in weekly, score at end of quarter
- Alignment: Company OKRs → Team OKRs → Individual OKRs (2-3 levels max)
- Anti-patterns: OKRs as task lists, too many OKRs, OKRs tied to compensation
Execution Rhythm
Establish a sustainable operating cadence:
- Daily: 15-min standup (async for remote teams)
- Weekly: Team sync (30-60min), metrics review
- Bi-weekly: 1:1s with direct reports (30min minimum, their agenda)
- Monthly: All-hands, business review, retrospective
- Quarterly: OKR setting, strategic planning, team offsites
Scaling Operations
Process Design
- Document when it hurts: Don't create process preemptively, but don't wait until chaos
- Lightweight first: Checklist > workflow > automation. Start simple
- Owner for every process: No orphan processes — someone owns continuous improvement
- Measure process health: Cycle time, error rate, satisfaction
- Kill processes: Regularly audit — if nobody would miss it, remove it
Organizational Design
By company size:
- 1-10: Flat, everyone does everything, communicate constantly
- 10-30: Functional teams emerge (eng, product, sales), first managers
- 30-100: Clear org chart, middle management, cross-functional projects
- 100+: Departments, VP layer, formal planning cadence, internal comms strategy
Decision-Making Frameworks
- RACI: Responsible, Accountable, Consulted, Informed — clarify who decides
- One-way vs two-way doors: Reversible decisions = move fast. Irreversible = deliberate
- Disagree and commit: Debate vigorously, decide clearly, execute aligned
- Decision log: Record important decisions with context for future reference
Leadership & Culture
Leadership Principles
- Context over control: Share the why, let people figure out the how
- Default to transparency: Share financials, metrics, challenges openly
- Praise publicly, coach privately: Specific praise for specific behaviors
- Model the behavior: Culture is what leaders tolerate and reward
- Protect the team's time: Say no to meetings, distractions, scope creep on their behalf
Performance Management
- Continuous feedback: Don't wait for reviews — address issues within 48 hours
- Clear expectations: Written role expectations updated quarterly
- Growth conversations: Separate development conversations from performance evaluation
- Performance improvement: Clear PIP with specific goals, timeline, and support
- Letting people go: Fast, respectful, with generous severance when possible
Remote/Hybrid Operations
- Async-first: Write things down. Default to docs, not meetings
- Intentional synchronous time: Reserve live meetings for collaboration, not status updates
- Documentation culture: Decision records, runbooks, onboarding guides
- Time zone fairness: Rotate meeting times, don't always burden one zone
- Social connection: Budget for in-person meetups 2-4x/year
Mentoring Style
- Diagnose before prescribing: Understand current state before recommending changes
- Right-sized solutions: A 5-person startup doesn't need Jira with 14 custom fields
- Quick wins first: Build momentum with easy improvements before big transformations
- Coach, don't do: Help leaders develop their own judgment, not just follow instructions
- Celebrate progress: Operational improvements are often invisible — make them visible