How to hire the right COO for your company's current stage

Executive overview

Most CEOs hire a COO without first understanding themselves — what drains them, what they're bad at, what they avoid. The role is not a fixed position; it's a yin-and-yang match that changes as the company scales.

A COO who's perfect at $2M–$100M will likely be wrong for $100M–$1B. The skill set, experience, and personality required shifts dramatically with company stage. Hiring for the wrong stage is the number one mistake.

The right COO isn't the best operator in the market — it's the best operator for your specific stage, sector, and personality.

What a second-in-command actually is

• The title can be COO, VP of Operations, Director of Operations, GM, or even an EA — what matters is the yin-and-yang dynamic with the CEO.
• True C-level titles require strategic input, real autonomy, P&L responsibility, and compensation in the $250K–$550K range.
• "Title inflation" — giving C-suite titles to $120K roles — obscures what you actually need and attracts the wrong candidates.
• The COO's core job is to make the CEO iconic internally; the CEO's job is to protect the COO externally.

Why the same COO can't scale indefinitely

• Cameron Herold was the right COO for 1-800-GOT-JUNK from $2M to $100M — franchising background, entrepreneurial autonomy, deep personal trust with the CEO.
• He was the wrong fit for the $100M-to-$1B phase, which required corporate operating experience at scale.
• His replacement: the former president of Starbucks USA.
• The current COO, Eric Church, would have been "incapable" in the early stage but has been exceptional for 12 years through the corporate scaling phase.
• Even within a single company, assume you'll need to replace the COO through two revenue doublings.

How to define what you need before you search

• Do an activity inventory: list everything you're bad at, everything that drains you, everything you avoid, every area you don't want reporting to you.
• Flip that list — it becomes the COO's job description.
• Check your Colby and DISC profiles; look for a personality counterpart, not a clone.
• Match the title to the actual scope and compensation — don't inflate either.

Finding and attracting candidates

• Use executive search firms that specialise in COO and senior operator roles; they poach from the market so you don't have to do it directly.
• Share the Vivid Vision early in the process — if a strong candidate doesn't connect with where you're going, keep searching.
• A compelling public Vivid Vision and strong employer brand draws A-players inbound without cold-calling competitors.

Interviewing for real skill, not described skill

• Most CEOs have had minimal training in interviewing — doing it 100 times wrong doesn't make you good at it.
• The key distinction: someone who knows how to do something versus someone who has done it and can prove it.
• Use the threat of reference check (TORC) process to surface honest assessments of past performance.
• Run multiple independent interviewers who rate the same candidate separately, then cross-reference.
• For roles outside your expertise (e.g., CTO, CFO), bring in domain experts to assess skill set; you assess culture fit.
• Use behavioural questions tied to specific traits. Example: "Describe your closet to me" reveals detail-orientation without leading the candidate.
• If a candidate claims a skill but can't demonstrate evidence of having applied it, treat that as disqualifying.

The 12 core leadership skills every team should develop

1. Situational leadership
2. One-on-one coaching
3. Delegation
4. Time management
5. Project management
6. Handling conflict
7. Interviewing
8. Running effective meetings
9. Reverse-engineering vision
10. Financial literacy (implied in P&L management)
11. Recruiting / hiring
12. (12th not recalled in session)

• Each skill has three competency levels: bronze (baseline), silver (proficient), gold (can certify others).
• Train your whole leadership team to at least bronze on every skill — most have trained only on what the company does, not how to lead.

Running meetings that don't waste time

• Almost no one has been trained to run meetings — that's why they feel broken.
• End every meeting five minutes before the scheduled close; announce this at the start.
• No agenda, no attendance: require a written purpose, outcome, agenda items, order, and time per item before anyone agrees to attend.
• Fewer attendees per meeting — if more than three or four topics, some people don't need to be there for all of them.
• Book meetings for half the time you first think you need; Parkinson's Law expands work to fill available time.

Using Vivid Vision to align the whole organisation

• A Vivid Vision is a four-to-five page description of what the company looks like, acts like, and feels like three years from now — written as if it has already happened.
• Covers every function: operations, sales, marketing, engineering, meeting rhythms, culture, dashboards.
• Share it with employees, customers, suppliers, and shareholders — alignment across all stakeholders is what drives execution.
• It's the one tool missing from every major operating system (EOS, Scaling Up, etc.) — add it in front of any OS to amplify results.
• Can also be written for an individual or a marriage; the same principle applies.

Lessons from being fired by his best friend

• Herold was let go by Brian Scudamore — his best man — after six years building 1-800-GOT-JUNK to $100M.
• The firing was correct in substance (wrong stage fit) but mishandled in execution — it took four years to rebuild trust.
• He knew it was coming; the lesson is that companies outgrow operators, and that's not a failure — it's a scaling milestone.
• The board, not the CEO, often mismanages these transitions; how a separation is handled determines whether the relationship survives.
• Every senior hire can likely stay through two revenue doublings; plan for transitions before they become crises.