How to find, hire, and work with a COO as your second in command

Executive overview

Most CEOs are visionary but struggle with execution — and trying to find another version of yourself only makes it worse. The second in command (COO, integrator, VP of operations) is the complementary counterpart who handles what the CEO doesn't love or isn't good at.

The relationship is closer to a business marriage than a reporting line. It requires trust, deep mutual understanding, and a clear separation of roles — and like any marriage, it has seasons that eventually end.

The COO isn't just an operator — they're the yin to the CEO's yang, and the match is as situational as a romantic partnership.

What a COO actually is

• Not a functional head — the role spans the whole organisation and requires interpersonal breadth over domain depth
• Must complement the CEO's specific blind spots, not just the generic role
• The right COO is stage-specific: a person who excels at 2M–100M may be wrong at 100M–500M
• Titles vary (COO, integrator, president, GM) — what matters is that someone "gets shit done" alongside the CEO
• Before hiring a COO, first hire an executive assistant to strip admin from the CEO's plate

How to find the right match

• Start with self-knowledge: where do you lose energy, what drains you, what are your goals for the company?
• Match on three axes: complementary skills to the CEO, right company stage, cultural and behavioral fit
• Don't assume a strong COO at one company will work at another — it's far more situational than functional roles
• Check internal candidates first; only go external when no one internal has both the capability and the desire
• Confidence without underlying expertise (common in younger hires) creates high-volatility performers — assess carefully

Building the CEO–COO relationship

• Treat it like a business marriage: scheduled time together away from the team, a private space for candid debate
• Run annual or rotating personality assessments (DISC, StrengthsFinder, Kolby) — not to change each other, but to deepen understanding
• CEO's biggest gift to the COO: "What else would you like to ask me?" — give time, not pressure
• COO's biggest gift to the CEO: communicate in sound bites; the CEO's brain is full
• When one is an activator and one is deliberative, negotiate explicit timelines ("I need until Friday") rather than letting it breed frustration
• Consider a shared coach or even a couples therapist-style facilitator for the partnership

The COO's first 90 days

• Month 1: Observe only — lunches, meetings, field visits, notebooks full of ideas. Do nothing yet.
• Month 2: Stress-test every idea from month one. Interview people, challenge your own hypotheses.
• Month 3: Implement easy wins first — low time, low money. Build visible momentum and trust before tackling big projects.
• Every change is a boulder: it reaches the bottom, but the ripple effects can outweigh the value if unexamined
• Don't rush key personnel decisions (e.g., firing a revenue-critical person without mapping consequences can destroy the business)

When you don't need a COO yet — and when the season ends

• You likely don't need a COO until you have solid functional department heads in place and the CEO can no longer develop people, only manage them
• When the CEO is going from meeting to meeting just keeping things moving, a second in command multiplies leverage
• The COO role has seasons: the person right for 0–100M is often wrong for 100M–500M
• Recognise the end of the season honestly — not as failure, but as the natural close of a chapter
• Exit with integrity: how the transition is handled matters as much as what was built together

Unlearning the school system

• For 18 years, school trains people to fix their weaknesses — get a tutor, work harder, reach average
• The entrepreneurial shift is the opposite: identify what you're brilliant at, delegate everything else
• Younger workers raised on collaborative gaming are better pre-adapted to this model
• A 50-year-old with "30 years experience" may really have five years of experience repeated six times — assess actual capability, not tenure