How to Find, Hire, and Keep the Right COO for Your Company

Executive overview

Most CEOs hire a COO too late, too fast, and without understanding what they actually need. The right second-in-command depends on the CEO's own strengths, the company's stage, and precise clarity on roles — not just on finding someone competent.

The CEO-COO relationship is a partnership that must be designed, not assumed. Get the match wrong and you lose momentum. Get it right and one plus one equals seven.

The $100 million mistake is hiring a COO who is right for the job description but wrong for the stage, the CEO, and the company.

Know yourself before hiring

• Map your own strengths, weaknesses, and behavioral traits before defining the role.
• Identify which areas energize you and which drain you — the COO fills the gap.
• The role definition flows from the CEO's profile, not from a generic job description.
• Hire someone who has actually done the job before, not someone who theoretically could.
• Poach from other companies; the right person is likely already employed.

Match the COO to the company stage

• An entrepreneurial, outward-facing COO is right for early hypergrowth; the wrong fit later.
• A process-oriented, inward-facing COO scales a mature organization but fails in the startup phase.
• 1-800-GOT-JUNK example: one COO took the company from $2M to $106M; a different profile took it from $100M to $450M — same CEO, same company, different stage.
• Shopify identified early that Tobi Lütke was inward-facing, so they needed an outward-facing COO — the inverse of the norm.
• Treat the organization like a human: you parent a two-year-old very differently from a twenty-three-year-old.

Onboarding: slow down to speed up

• Most problems occur when a new COO is pushed into execution too quickly.
• Allow 30–60 days of deliberate onboarding before the COO takes full ownership.
• The COO needs time to understand key relationships, internal history, and the "why" behind existing decisions.
• New COOs disrupt without knowing it — killing projects people spent a year on, hiring outside people, changing processes. Slow onboarding prevents unintended ripple effects.
• Follow the forming-storming-norming-performing model through the first 90 days.

Building the CEO-COO relationship

• Treat the relationship like a marriage: it requires deliberate maintenance, not just proximity.
• Schedule a weekly sync — non-negotiable, never cancelled. Missing it repeatedly causes drift.
• Create time outside day-to-day operations to plan, connect, and rebuild trust.
• Divide responsibilities cleanly — when both people run the same function, neither gets leverage.
• CEO and COO should shine the spotlight on each other internally and externally.
• Both should attend board meetings; the COO prepares materials, the CEO holds the relationships.

Communication and trust protocols

• Establish clear communication protocols from day one.
• One person — the CEO — should be the primary contact with the board, not both independently.
• The COO stays in sync through weekly rhythms, not ad-hoc updates.
• Doing each other's jobs creates frustration; clarity on who owns what prevents it.

The "Chief of Staff" misuse problem

• The Chief of Staff title came from government; most companies misapply it.
• A true Chief of Staff does three things: controls all communication in and out, manages the CEO's calendar entirely, and oversees all leadership deliverables and projects.
• If the CEO is not fully delegating all three of those functions, they don't need a Chief of Staff — they need a strong executive assistant.
• Most CEOs and COOs need executive assistants, not Chiefs of Staff.

AI and staying relevant as an executive

• Executives who do not adopt AI tools will be displaced by younger operators who do.
• ChatGPT is one of roughly 15,000 AI tools currently available.
• Companies should allocate one to two hours per week for employees to experiment with AI tools.
• The analogy: refusing to use Wi-Fi or a laptop in 2001 would have ended your career. AI is that inflection point now.