Chapter 1
The Second in Command: Unleashing Your Business Through Strategic Partnership
Imagine walking into a boardroom where the CEO and COO sit side by side, finishing each other's sentences and transforming ideas into action with seamless precision. This isn't just organizational harmony-it's rocket fuel for business growth. When Brian Scudamore of 1-800-GOT-JUNK? found his perfect second-in-command in Cameron Herold, they catapulted the company from $2 million to $106 million in just six years. This "business marriage" has become the stuff of legend, with entrepreneurs at conferences whispering, "I need a Cameron."
The Second in Command has garnered praise from business leaders across industries who recognize the transformative power of the right CEO-COO partnership. This relationship-often misunderstood and undervalued-can be the difference between a company that plateaus and one that soars. As Mark Zuckerberg demonstrated by highlighting Sheryl Sandberg's contributions at Facebook, the right operational leader doesn't diminish the CEO's vision but amplifies it exponentially.
Chapter 2
Finding Your Perfect Complement: The COO Defined
The Chief Operating Officer defies simple definition. Unlike other C-suite roles with clear parameters, the COO position varies dramatically across organizations-so much so that Cameron Herold created the COO Alliance spanning seventeen countries to fill the void where industry groups for these executives should exist.
What makes the COO role unique is its chameleon-like quality. The fundamental requirement is that "the COO has to be great at whatever the CEO sucks at." This creates a complementary yin-yang relationship that, when properly aligned, can transform organizational performance.
Research by Bennett and Miles identifies seven distinct COO archetypes, each serving different organizational needs:
The Executor handles daily operations while the CEO focuses on long-term vision-turning ideas into reality through effective implementation. The Change Agent, typically hired from outside, oversees major transformations like turnarounds or growth phases, bringing fresh perspective to drive organizational pivots. The Mentor supports inexperienced CEOs, particularly young founders whose companies have scaled faster than their managerial abilities-as Sheryl Sandberg did for Mark Zuckerberg at Facebook.
The Other Half creates balance through complementary skills-being strategic when the CEO is tactical, or handling details when the CEO focuses on vision. The Partner co-leads with the CEO, appearing alongside them on the org chart to free the CEO from overwhelming workloads. The Heir Apparent serves as a potential successor, learning all aspects of the business while proving leadership capabilities. The MVP emerges when a company promotes an exceptional internal leader to retain their talent-like Harley Finkelstein at Shopify who rose to COO before having full experience because he embodied the right perception of the company.
These categories provide a useful framework, but roles often blend together. COOs can transition between types or embody multiple types simultaneously. The key is finding the right fit for your specific situation.
Chapter 3
The Purpose Behind the Position: What COOs Actually Do
A COO transforms vision into reality, serving as the connective tissue between departments and processes. While there's no universal template, effective COOs share certain traits: strategic thinking, people development skills, and the ability to focus on critical priorities.
The inward-outward dynamic is crucial to understand. Some CEOs become the public face of their brand like Steve Jobs or Elon Musk, requiring an inward-facing COO focused on behind-the-scenes operations. Others are more technically focused, benefiting from an outward-facing COO who serves as the company spokesperson. At Shopify, Harley Finkelstein was the public-facing COO handling media while CEO Tobias Lutke focused on product engineering. The key is creating an effective partnership where executives approach business differently but are more effective together.
A COO functions like a quarterback-calling plays and passing the ball while trusting others to fulfill their roles. They don't need deep expertise in every area, but rather must communicate effectively with all departments. While department heads are specialists, COOs are generalists who understand everyone and know how to hire experts. Using the Socratic method, they ask the right questions to align business areas, fix broken systems, and bring out the best in their teams.
The COO's job isn't to fix problems directly but to grow others so they can solve problems themselves. Like a parent teaching children self-sufficiency rather than doing everything for them, a good COO hovers above the trenches, coordinating rather than getting sucked into doing employees' work. Their role is to lead people to do rather than doing directly, finding leverage points in messy situations.
A good COO sees shortcuts, embraces innovation, learns quickly, and hacks systems. They understand that momentum creates momentum, focusing on getting things done rather than perfection. They also look beyond the business to external factors-customers, suppliers, markets, economy-feeding that information into company strategy. At 1-800-GOT-JUNK?, Cameron anticipated the strengthening Canadian dollar and implemented hedging strategies that saved hundreds of thousands of dollars.
The COO must balance strategic and tactical roles, toggling between high-level vision and day-to-day operations like "a whale coming up for air and then diving back down to feed." While CEOs typically handle strategy, COOs manage tactics-both essential components as Sun Tzu noted. For maximum effectiveness, CEOs must allow COOs to share the strategic view rather than limiting them to tactical firefighting.
Chapter 4
When to Bring in Your Second-in-Command
The right COO brings exponential power to a CEO, creating a complementary "two in a box" dynamic-but only if you understand what you need. Finding the right second-in-command starts with self-reflection to identify what will improve your business, make your life better, and increase your effectiveness.
The best starting point is an Activity Inventory, categorizing all your tasks into four types: Incompetent (you're bad at it), Competent (you're okay at it), Excellent (high skill but don't love it), and Unique Ability (what you're best at and would do for free). Your Unique Abilities are often hard to recognize because they come naturally to you. The goal is to delegate everything that isn't your UA-first the incompetent and competent tasks, then the excellent tasks you don't love-to build out a job description for your second-in-command.
Tasks outside your Unique Abilities drain your energy and the company's. The right COO frees you to focus on what you love and energizes you, allowing you to be the "chief energizing officer" who brings positive energy to the organization. By delegating energy-draining tasks to your COO, you multiply your effectiveness and the organization's capacity.
Every CEO will eventually exit their company, whether through sale, retirement, or death. A COO helps position the company for this inevitable transition by building systems that ensure the organization can run itself without relying solely on the current CEO. This creates resilience and longevity, potentially with the COO becoming the heir apparent.
Being a CEO is often lonely-you can't fully confide in your board, employees, or even spouse without risking negative consequences. A trusted COO provides essential partnership, someone you can be vulnerable with who will tell you the truth when needed. Unlike other roles where personal connection is secondary, it's vital to hire a COO you genuinely like and respect, someone you'd enjoy spending time with outside work.
The right CEO-COO partnership creates exponential growth, not just doubled productivity. At 1-800-GOT-JUNK?, Cameron and Brian were "like nitroglycerin," igniting rapid expansion through complementary skills and mutual trust. The key was Brian sharing his "Vivid Vision" while being willing to step aside and let Cameron execute it.
Chapter 5
Alternatives to Consider Before Making the Hire
Don't hire a COO if you don't need one-despite their transformative potential in the right situation, they represent significant expense and commitment. Consider alternatives first, as the wrong person can be worse than no one.
Before hiring an expensive COO, try getting an Executive Assistant to handle administrative tasks. As Jack Daly says, "If you don't have an assistant, you are one." If you constantly feel overwhelmed and think "I just need some help," start by delegating administrative tasks from your activity inventory to an EA. Only consider a higher-level second-in-command if you still have significant responsibilities to offload.
If you need expertise in specific domains rather than overall coordination, consider hiring functional heads instead of a COO. When facing issues in particular areas, a CFO, CTO, or VP of Marketing might be more appropriate and less expensive. A COO doesn't necessarily have deep expertise in any one domain, but brings strength across multiple areas with focus on people and strategy.
Before hiring someone to handle projects you can't manage, consider whether you have too many core projects. You might be better off scaling back than adding headcount. Ironically, a good COO might come in and quickly identify that you have too many projects, suggesting you focus on "the critical few versus the important many."
Consider hiring a Fractional COO-typically a former senior executive who works for multiple companies rather than just one. This relatively recent development allows small or midsize companies to access COO-level expertise without paying a full-time salary. A Fractional COO can lead core projects, coach executive teams, and help scale operations while giving the CEO a taste of how they might eventually work with a full-time COO.
Even after exhausting alternatives, pause to consider whether you can truly afford a COO. This hire must pay for itself by adding more value than their salary costs. As a rule of thumb, every employee should return a minimum of 2X-preferably 4X-on their pay to generate the gross margin needed to break even on their cost.
Hiring a COO creates organizational ripples-it's like dropping a boulder in your company pond. Unlike other management roles that integrate seamlessly, a second-in-command's arrival can trigger resentment, pushback, or even resignations from existing department heads. This isn't a short-term fix; it's a commitment with long-lasting impact.
Chapter 6
The Strategic Hiring Process: Finding Your Perfect Match
Finding the perfect COO begins with understanding yourself. Your activity inventory has identified your Unique Abilities and weaknesses-now seek someone who complements them. The ideal second-in-command typically possesses strengths opposite yours while sharing your core values. Spend focused time crafting an extremely specific job description that includes required behavioral traits, areas of responsibility, and clear boundaries about what remains under your purview.
The CEO-COO relationship should be visualized not as leaders at the top of the hierarchy but as supporters at the bottom of an inverted org chart. Together, they form a "two in a box" partnership that serves the organization by removing obstacles, providing support, and aligning and inspiring people. This servant leadership approach might seem foreign to old-school business models, but the traditional hierarchical structure simply doesn't work anymore.
To clarify what you need in a COO, "lean out into the future." Envision your business three years from now-what will it look, act, and feel like? How must your org chart evolve to achieve this Vivid Vision? This future-focused clarity helps you reverse-engineer the skills and personality needed in your second-in-command.
Traditional education teaches us to have all the answers-a ridiculous goal. Instead, effective leaders know who to find for solutions, not how to do everything themselves. As Dan Sullivan and Ben Hardy explain in "Who Not How," you solve problems by finding the right people. Your COO should excel precisely where you struggle.
Your COO must align with your company's core values-those non-negotiable principles you'd fire someone for violating. It's far easier to hire someone who already lives by these values than to convert someone who doesn't. The key is distinguishing between true core values and those that are merely nice to have.
Finding a COO is comparable to finding a spouse. You need crystal clarity on what you're looking for, with non-negotiable essentials rather than "nice to haves." You're seeking trust, aligned core values, complementary behavioral traits, skillsets, strengths, and desires-all with personal chemistry that might develop into friendship. Like marriage, you won't be able to change their personality after hiring, so focus on finding the perfect fit from the start.
Finding the perfect COO is challenging as top-level candidates are rarely unemployed and usually not job hunting. You'll likely need to poach them with help from search firms, online postings, and your network. The hiring process requires careful planning and transparency with your team to ensure a smooth transition.
When deciding between promoting from within or hiring externally, consider your company's needs. Internal hires make sense when deep technical knowledge or industry focus is required. However, this approach risks creating perceptions of favoritism and limits your candidate pool. External hires bring fresh perspectives but face challenges understanding company history and culture.
The title you choose for your second-in-command matters significantly. "Second-in-command" may be preferable to "COO" as it provides clarity and flexibility. In smaller companies (20-30 people), Director or VP of Operations might be more appropriate than COO. Your job title must align with both responsibilities and compensation, which correlate with company size.
Create a tailored scorecard for your COO search based on the top five things they must accomplish in their first year for the hire to be successful. For your job description, write it like you're telling your best friend about the role, then have a professional copywriter polish it to make it compelling. The goal is to attract candidates who have actually done the work before, not just those who know how to do it.
Your COO needs vary dramatically by company size. Small businesses (under 50 employees) need jack-of-all-trades COOs who can build management teams and handle various tasks as the company scales. Medium businesses (50-200 employees) require someone who can build strong leadership teams and bring domain expertise. Large businesses (200-500 employees) need seasoned COOs focused on collaboration, problem-solving, and strategic thinking rather than direct management.
I maintain a "virtual bench" of talented people I might want to hire someday, even when not actively recruiting. I'm always looking for potential fits for future roles, knowing the best people likely already have jobs. I'm comfortable recruiting them away from average companies to join great ones-it's like moving a great soccer player to a better team. Your future COO is working somewhere today, likely at a top company, and you need to poach them.
During interviews, ask candidates to submit a 3-4 minute video explaining how they can help make your vision reality. I don't even read resumes until receiving these videos, which serve as initial culture-fit screening. By screening for culture fit first, you'll interview fewer people more thoroughly, creating a high-quality shortlist for deeper skills assessment.
Before hiring your second-in-command, you should know so much about them and be so confident that on day one, you'd happily give them your master password, bank account information, house keys, and trust them with your children. If that complete, implicit trust isn't there, don't make an offer. It's that simple.
Chapter 7
Onboarding for Success: The Critical First 90 Days
A new COO's arrival creates ripples throughout the organization. Done well, it frees the CEO to focus on their unique abilities; done poorly, it disrupts the entire business. The CEO must remain engaged during this transition period, just as parents must both be involved in raising children.
The onboarding process should follow a clear three-month structure: Month 1 is for understanding through observation and note-taking; Month 2 is for identifying opportunities to improve systems and processes; Month 3 is when the COO can begin implementing changes based on their accumulated knowledge. Moving too quickly damages relationships and trust, while proper onboarding builds the foundation for effective leadership.
Onboarding is complete when the COO has met every benchmark in the process-meeting one-on-one with every VP and Director, attending business area meetings, reviewing project plans, understanding the Vivid Vision, talking to suppliers and customers, comprehending the sales cycle, and completing company trainings. This thorough process builds trust and understanding before the COO takes over project direction.
Matt MacInnis, COO of Rippling, created a personal operating manual that he shares with everyone in the company. This document outlines how he operates, what drives him, what frustrates him, and how he makes decisions. This approach helps prevent disruption by giving others insight into how to work effectively with him. Imagine if everyone created their own operating manual-it would help teams work together more efficiently.
Onboarding a COO gets them into the organization, but their growth can't stop there. The COO Alliance fills a crucial gap-a thought leadership group exclusively for seconds in command from companies with at least $5 million in revenue. It's a trusted community of executives from seventeen countries who share ideas, solve problems, and develop together.
The CEO and COO share the same box, and both need to expand their horizons. Like executives tasked with clear-cutting a forest, they might be cutting perfectly-but only by climbing the tallest tree will they realize if they're in the wrong forest. The Alliance transcends differences through "ideas having sex"-members learn from various systems to create something better for themselves.
New ideas typically enter organizations through CEOs, who often belong to mastermind communities with exposure to thought leadership. But COOs should also actively seek new tools and resources, reading books, finding courses and mentoring opportunities, and implementing best practices. Just as CEOs need networking groups, COOs benefit from mastermind communities where they can build connections.
Chapter 8
Building an Effective Partnership: The Dance of Collaboration
The CEO-COO relationship should mirror parents who present a united front. The COO's job is to make the CEO iconic-the CEO delivers good news while the COO handles tough decisions and bad news. In return, the CEO must support the COO internally when difficult calls are necessary.
Erik Church, COO of O2E Brands, compares the CEO-COO relationship to Walt and Roy Disney. Though Roy was co-founder, the company was named after Walt, the visionary. Erik believes a COO should implement the CEO's vision with enough ego strength to judge themselves solely by results, not public credit. He describes his partnership with Brian Scudamore as "two sides of one coin" with complementary strengths and weaknesses. They debate privately but present unified positions publicly.
Regular "date nights" away from the office help build the foundation of trust and friendship that powers the organization. These weekly meetings might involve sports, drinks, or simply working side-by-side in a different environment. TJ Hock of Rentwell takes biannual trips with his CEO, sometimes focused on spirituality and business, while also reading the same books and occasionally gathering their families. These touchpoints create an "incredible bond" that strengthens their professional relationship.
Skip-level meetings-where CEOs meet with employees who report to the COO-require careful handling. These meetings help CEOs maintain relationships and generate ideas without undermining the COO. The CEO should focus on learning and asking questions rather than making commitments or solving problems on the spot. After gathering insights, the CEO should discuss findings with the COO, who has more context about team dynamics and capabilities.
Effective COOs must focus on delegation rather than doing everything themselves. Looking back at my time at 1-800-GOT-JUNK?, I should have delegated more tasks sooner to focus on growing and aligning people. The question should shift from "How quickly can I get this done?" to "Who else could do this work?" This balance between short-term speed and long-term efficiency is crucial for scaling.
COOs risk burnout when they don't maintain work-life balance. Working 50-70 hour weeks and skipping vacations leads to stress and poor decision-making. When I surveyed my direct reports as COO, they wanted me to take more time off and be less stressed-they didn't want to feel that workaholism was required for success. A COO's work is never done, but they must stay balanced to think strategically rather than solving everyone's problems.
Regular, structured communication between CEO and COO is essential. Beyond social bonding, formal weekly meetings help ensure alignment on priorities and challenges. At 1-800-GOT-JUNK?, Brian and I had weekly one-on-ones, frequent informal connections, and worked side-by-side to stay synchronized. We also maintained weekly leadership team meetings, monthly financial reviews, quarterly planning sessions, and annual two-day strategic planning meetings.
Chapter 9
Redefining the CEO Role: Leading Through Partnership
When a COO joins the organization, the CEO's role fundamentally changes-often in unexpected ways. While hiring a second-in-command frees the CEO from operational responsibilities, letting go can be challenging. CEOs must recognize that the COO is a partner, not a threat, and learn to be vulnerable. The transition requires redefining the CEO's role and resisting the urge to cling to familiar responsibilities.
As CEO, transitioning from having the entire company depend on you to delegating to a COO requires learning to let go. This newfound time allows you to focus on strategic thinking, planning for the future, and leveraging your unique strengths. One coaching client discovered his company had nearly 200 concurrent projects-an impossible workload-and eliminated 150 of them. This strategic decision, possible only because he had time to think, dramatically reduced organizational stress and focused efforts on critical priorities.
CEOs must avoid "seagull management"-swooping in, criticizing, and leaving without resolution. When you notice issues, pull the COO aside privately rather than undermining them publicly. Entrepreneurial CEOs often feel insecure when sharing praise and recognition with a COO, but people respect you more for bringing in help to grow the company. Remember that interfering with the COO's work, even with good intentions, undermines their authority and effectiveness.
Dan Sullivan's concept of Unique Ability teams focuses on areas where individuals excel and feel energized. CEOs should delegate everything except their genius work-keeping only what aligns with their Unique Abilities while letting the COO handle the rest. Most CEOs retain 3-5 business areas they love or are strategically important, like Steve Jobs keeping product design but not retail. The COO should help build teams where everyone works primarily in their Unique Ability areas, using an activity inventory to identify and redistribute tasks.
Conflict between CEO and COO is natural, like in any close partnership. When addressing issues, focus on specific situations rather than attacking the person. Express how you feel about what happened and ask for their perspective. Keep disagreements private-arguing in front of employees sends negative ripples throughout the organization. Don't involve HR as an arbiter; they should coach you on solving your own conflicts.
Both CEOs and COOs must check their egos at the door. COOs need humility and drive to build consensus and earn respect, while CEOs require confidence without arrogance. Ego leads to back-channeling and employee turnover-people don't want to work for assholes. Jim Collins' Level 5 leadership combines personal humility with strong will. COOs must accept that CEOs typically get most of the limelight, though sometimes sharing recognition makes sense.
Chapter 10
When the Partnership Ends: Navigating Transitions
The CEO-COO relationship, despite deep investment and friendship, rarely lasts forever. As businesses evolve through different phases, the COO role changes significantly while the CEO's core function remains more consistent.
Unlike CEOs who can maintain their core skill set while delegating tactical responsibilities, COOs must continuously evolve their capabilities as the organization scales. The demands on a COO shift dramatically as a business matures, requiring them to adapt their skills to remain effective-much like athletes who must develop to stay competitive as they advance. Most senior people can only take a business through two doubles in revenue before struggling with the third.
When Brian brought me in to help build 1-800-GOT-JUNK?, it had $2 million in revenue and twelve franchises. By the time it reached $106 million with 330 locations and 3,000 employees system-wide, Brian needed a highly detail-oriented COO-not my entrepreneurial growth skillset. When he asked to meet for breakfast, I knew it was over. We both cried, but I knew he was right. I wasn't enjoying it as much anymore and felt out of my league. After taking time off to reflect, I reinvented myself as a CEO coach and speaker.
Brian's next hire-the former Starbucks president-had the skills but wasn't a cultural fit and lasted only a year. Finally, he found Erik Church, who had both the skills and cultural alignment to take the company from $100 million to $1 billion-proving that hiring the right COO is difficult but worthwhile.
If the COO stops buying into your Vivid Vision, they should leave. Their purpose is making your business dreams reality, and if they're no longer aligned with those dreams-or if their skills no longer match the company's needs-they're out. The COO is like a booster rocket, pushing you higher until they burn out at a certain level. Then you can hire a new one to take you further. Even when you feel your business has gone as far as it can, there's a COO out there who can take you further-you just need to find them.
The right second-in-command can transform your business, your life, and your leadership effectiveness. By understanding what you need, finding the perfect match, and building a strong partnership based on trust and complementary skills, you create the conditions for exponential growth. Remember that no CEO has to go it alone-with the right COO by your side, you can achieve more than you ever thought possible.
