PDF Summary:The Second in Command, by Cameron Herold

As a CEO, it often feels impossible to manage and grow an entire company while getting the results you want—and according to Cameron Herold, that’s because it usually is. It’s unrealistic for a CEO to have the expertise to manage every area of their business—this is why they have COOs. A COO is like a CEO’s perfect puzzle piece, allowing the CEO to focus on the things they’re best at and leave the other areas in safe hands. In The Second In Command, Herold explains how to hire and utilize a COO to take your business to the next level.

In this guide, we’ll discuss what a COO does, whether you need one, how to find one, how to integrate them into your company, and how to know when to let them go. In our commentary, we’ll help you put Herold’s advice into action with recommendations from other experts like Patrick Lencioni (The Advantage), Geoff Smart and Randy Street (Who), and Michael Watkins (The First 90 Days).

(continued)...

Once you’ve figured out the responsibilities you need a COO to take on, determine what level of support you need. it’s possible that you may not need someone as serious as a COO—taking on a COO is a long-term commitment that will have a financial and cultural impact on your company. Herold says to consider the following factors:

1. If the tasks you would designate to a COO aren’t super high-stakes and you’re more looking to free up your time, can you hire an executive assistant instead?

(Shortform note: Executive assistants usually perform tasks like organizing documents, answering and returning phone calls, keeping records, taking notes at important events and meetings, scheduling, and other administrative duties.)

2. Instead of a COO, can you hire department heads and designate your high-stakes tasks to them? For example, could you hire a head of finance or head of marketing?

(Shortform note: Most businesses have the following departments (and department heads) that you should consider delegating tasks to before hiring a COO: human resources, operations management, information technology, marketing, sales, accounting and finance, and research and development.)

3. If you don’t have that many high-stakes tasks to designate, can you hire a part-time COO who also works for other companies?

(Shortform note: Part-time or “fractional” COOs usually have a limited number of tasks they can take on since they don’t work full-time and aren’t the CEO’s counterpart to the extent a full-time COO would be. They’re typically limited to tasks like strategic planning, process management, project management, and team development.)

4. If your high-stakes tasks are temporary crises that will go away once solved, can you hire a consultant to help you work through them rather than a COO?

(Shortform note: There are many types of business consultants to consider based on your needs. For example, communications consultants help you manage your image (both inside and outside of the organization), environmental consultants help you monitor your company’s environmental impacts, and legal consultants advise you on legal affairs.)

How to Find a COO

Once you’ve determined what kind of COO you need (if you need one), Herold says it’s time to start the process of finding one. To find a COO, you’ll need to create a clear and detailed job description, get the word out there to potential hires, and conduct in-depth interviews.

Create the Job Description

To write a job description that will attract the perfect COO, you’ll need to include the superpowers you want them to have (which you would have identified in the previous section), the business areas they’ll manage and the responsibilities they’ll have (consider the COO types and roles discussed above), and the personality traits and values you want them to have.

(Shortform note: In Who, Geoff Smart and Randy Street reiterate the importance of creating a job description that includes the skills, roles and responsibilities, and personality traits you want your hiree to have. They also emphasize the importance of keeping your description of these elements as short as possible and not using jargon—this will ensure that your needs are easily understood and that you and the candidates are on the same page.)

When considering the personality traits and values of your COO, be sure to take into account your personality and your desired company culture. Since the COO will have a close relationship with you and you’ll spend a lot of time together, they should be someone who you can get along well with and who shares similar values and perspectives—they shouldn’t have personality traits that get on your nerves, for example.

(Shortform note: To help find your perfect personality match, consider taking a personality test like the Myers-Briggs (MBTI) test and looking for someone with complementary traits. For example, research shows that in romantic relationships, couples in which both people are deemed “sensors” and “judgers” by the MBTI pair well, as do couples in which both people are “intuitors” and “feelers.” While a CEO-COO relationship isn’t romantic, these pairings may still influence compatibility since they require such a high level of closeness—Herold often refers to COO-CEO relationships as a “marriage.”)

Further, since the COO is the model of your company culture, you need to be sure they already align with the core values and behaviors of that culture before they apply for the job. According to Herold, it’s nearly impossible to change who someone is as a person, so you need to ensure they’re the person you need when you hire them and not afterward.

(Shortform note: In The Advantage, Lencioni reiterates the importance of hiring people who already align with the company culture, since it’s unlikely you’ll be able to change their values and behaviors. To determine the proper values and behaviors to define your culture, he recommends considering not only the traits you want your culture to uphold, but the positive traits that are already represented in your culture. Further, when listing these components, avoid one-word descriptions like “compassion” and instead opt for more specific and actionable descriptions like “willingness to seek others’ perspectives and offer help.”)

Finally, create a detailed future vision of your company and outline what the COO will need to accomplish within their first year of work. This outline will help the COO determine if they have the experience and abilities to meet your expectations, and you’ll use this outline to measure their success should they be hired. When creating your outline, consider things like your high-level goals, business strategies, financial goals, cultural goals, and so on.

(Shortform note: Smart and Street reiterate the importance of clarifying the goals of the role you’re offering on the job description. In particular, the authors recommend including three to eight goals. To make them most effective, ensure these goals are clear, objectively measurable, and have specific deadlines.)

Start the Search

Once you have a job description written up, Herold says you must start your search by first determining whether you want to hire from inside or outside of the company. Internal hires can be great because they already know the company and may already have a close relationship with you; however, only hire internally if this person is your perfect fit. If you try to make a COO fit who doesn't perfectly align with everything you’re looking for, you’ll only cause more problems in the future.

(Shortform note: One major advantage of hiring internally that Herold doesn’t address is that, if you already have a great company culture that you don’t need to change, an internal hire is much more likely to be able to align with and model the culture. And as Herold explains, this alignment is one of the most important aspects when selecting your COO.)

When searching for an externally hired COO (which is most cases), you must spread the word about the open position across as many mediums as possible. Since they’re so valuable, the best people for the job are often hard to find—they’re usually already working for someone else and you’ll likely need to poach your COO from another company.

To reach these high-value people, post your job description on social sites like LinkedIn and Facebook and have your employees do the same. You can also post in any business groups you belong to or reach out to people directly through email. Another option is to work with an executive search firm—a recruitment service that will help you find a high-value person to fill the role you’re looking for in exchange for a fee.

(Shortform note: Instead of following traditional methods of recruitment like hiring a firm or posting your job listing, the authors of Who recommend using an ongoing referral process to create a talent pool you can pull from when the time comes to hire someone new. To do this, regularly ask people whose skills and knowledge you respect to introduce you to people they think would thrive in your organization. You should ask for a referral every time you meet someone you respect. Then, cultivate relationships with these referrals and stay in touch—this will make them more likely to seriously consider your offer if and when you reach out.)

Conduct Interviews

Once you find a few candidates that might fit the bill, Herold says you must interview them yourself to ensure they’re the right fit. In the first round of interviews, determine whether each candidate’s values and behaviors align with your personality and your desired company culture. If they don’t align on this level, there’s no point wasting your time with further interviews, as these aspects can’t be taught.

(Shortform note: Determining someone's true personality and behaviors can be difficult, especially when they know what you’re looking for and can tell you exactly what you want to hear. Luckily, experts say there are a few questions you can ask to get a closer look at someone's true personality. For example, ask them who their hero is, what they do in their free time when they have no plans, what their most vivid memory from childhood was, or what they think the most significant issue with society is. Their answers will expose their values, habits, and personality traits.)

After narrowing down the candidate pool to about five people, conduct a second round of interviews to determine whether or not the candidates have the skills you need. Do they have the superpowers you’re looking for and the ability to accomplish the components of your outline? You’ll probably want to include department heads during this interview stage who can help you determine the candidates’ skills in the areas you’ve outlined but don’t have expertise in—for example, the financial head or the marketing head. You should also ask for references in this interview who can verify the candidate’s skills.

(Shortform note: In addition to determining whether a candidate has the right skills, experts say you should pay equal attention to whether they have the wrong skills. Even the perfect candidate can cause more harm than good if they possess any of the following qualities: they lack structure and discipline, they’re ego-driven, their leadership style is based on emotion and ideology rather than strategy and rationale, they struggle to make decisions, they get stuck on small details, or they’re too independent.)

In the next interview, Herold recommends spending substantial time asking the candidate what each of their references would say regarding their alignment with the criteria on your job description. This will allow you to ask probing questions and get the best insight into the person’s true personality and abilities.

(Shortform note: The purpose of asking your candidate what their references would say about them is to get a deeper read on their abilities and behaviors. In Who, Smart and Street recommend achieving the same goal by having the candidate discuss each job they’ve held in the last 15 years in sequential order—this allows you to see both how they’ve changed and stayed the same so you can better judge their future trajectory.)

Once you’ve narrowed down your top choices, conduct thorough background checks. Call each one of the candidate’s references and ask them how well they think the candidate aligns with each of the criteria you’ve listed on your job description—especially their values. Press them to be completely honest, even about the bad things. By the time you finish your background check, you should entirely trust the person you chose to hire.

(Shortform note: In The Ideal Team Player, Patrick Lencioni offers some additional tips to make your background checks more effective so you get the information you’re looking for. For example, put people at ease by assuring them that their answers won’t be the determining factor for your decision. Further, ask references about the qualities you’re most unsure of in a candidate. Take note of instances when they dodge the question or refrain from answering—if they don’t have something positive to say, there could be a problem they’re hesitant to discuss.)

Integrate Your COO

Once you’ve hired the perfect COO, Herold says it’s time to integrate them into the company. This requires you to onboard them and foster your working and personal relationship with them.

Onboarding

Herold says the onboarding process should take roughly three months. Be sure to outline all the important benchmarks you want the COO to meet during this time—for example, meeting with each of the department heads individually, completing the standard employee training, speaking with customers, and so on.

In the first month of onboarding, the COO should simply observe you and the organization. They should start to meet the other leaders in the company, sit in on meetings, and observe how everything works and fits together.

In the second month, the COO should start to look for opportunities to change aspects of the business to achieve the criteria in your outline. This may include altering systems, strategies, and even people in the organization.

In the third month, the COO can finally start executing on some of the changes they’ve identified in month two. In doing so, they should map how they’ll conduct these changes and in what order to ensure things go smoothly and that they’re not taking on too much at once or causing unnecessary disruptions.

During the onboarding process, the COO and their direct reports should get well-acquainted with each other. To ensure clear communication and productive working relationships, the COO should learn about each person’s personality, communication styles, work history, and so on. In the same vein, the COO should also share this information about themselves with their reports.

How to Learn a Company in 90 Days

In The First 90 Days, Michael Watkins emphasizes the importance of the first 90 days of a leader's employment—this is when they should be meeting the onboarding benchmarks, learning about the company, and getting to know the people and processes they’re working with. Watkins provides a detailed list of tasks that should be completed within this time frame; however, he doesn’t explicitly state when each task should be done. Let’s use Herold’s time frame and Watkins’s detail to create an actionable onboarding agenda:

Watkins provides a few additional tasks to complete to get a solid grasp on the people and processes of the company in the first 30 days. For example, have the COO meet with external observers of the company, such as predecessors, former employees, and business partners, to get an outside view of the culture and politics. You should also have the COO meet with all their direct reports during this time frame—Herold recommends doing this but doesn’t specify when in the process it should happen.

In the second month, Herold recommends that the COO start looking for areas of the business that can be improved or need to change. To do so, Watkins recommends using the STARS model to identify what stage the business is in and determine which changes to prioritize accordingly.

If the business is a start-up, the COO should focus on organization and implementation of success strategies. If the business is in a turnaround, the COO will need to determine immediate actions to redirect the company’s trajectory. If the business is in accelerated growth, the COO needs to develop new structures, processes, and personnel to level up the business. If the business is in realignment (it’s stagnant), the COO will need to motivate employees and inspire a sense of urgency to take the business to the next level. If the company needs to sustain success, the COO will need to cycle back through the startup, turnaround, and acceleration phases to create a dynamic and sustainable success strategy.

In the third month, Herold recommends the COO start implementing the changes they've identified. To ensure the changes are effective, Watkins recommends that the hiree talk to the boss about which STARS changes are most applicable to the business (this will help the COO map out their changes, as Herold recommends). Further, they should review the resources they have available to orchestrate the changes—for example, finances, technical assistance, public support, and so on.

Building Your Rapport

According to Herold, building a close relationship with your COO is just as important as the onboarding process—for the business to run as smoothly as possible, you and your COO should have an intimate understanding of each other and should share mutual trust. This will help you overcome issues and present a united front to others in the company. To do this, you must build not only a solid working relationship, but an intimate friendship as well. Since your COO’s personality intentionally complements yours, this shouldn’t be too difficult.

To start off, you and your COO should discuss your backgrounds and histories—for example, hardships you've faced, accomplishments you're proud of, your fears, your family life and childhood, and so on. You should also take personality tests and share your profiles with each other.

(Shortform note: In The Advantage, Lencioni argues that fostering personal relationships in the workplace to build mutual trust is critical because it creates a safe environment—a crucial factor in organizational health, which determines whether an organization will thrive. However, sharing personal histories and personalities are only two of the ways to build a safe environment. Lencioni also recommends discussing the fundamental attribution error—an inherent human tendency to make excuses for our mistakes while unfairly attributing others' mistakes to their personality. Keeping this in mind will help coworkers avoid making the fundamental attribution error which will result in healthier communication and more respect among counterparts.)

To further promote friendship between you and your COO, Herold recommends regularly meeting up outside of work just to hang out—this isn’t to talk about work, but to just have fun and get to know each other better.

(Shortform note: Hanging out in person, as Herold recommends, isn’t always possible if the CEO and COO live in different places or the company is fully remote. To build a close relationship despite these difficulties, consider conducting virtual hangout sessions—happy hour video chats, virtual storytelling sessions, or even hangouts where you teach each other fun skills you have like knitting or making your favorite dish.)

When to Let Go

While hiring a COO is a long-term commitment, Herold says that in most companies, there will come a time when the current COO is no longer a fit. People and companies are always growing and evolving, and it’s not guaranteed that your COO will still align with the vision you have for the company after a few years.

(Shortform note: Research shows that COOs aren’t permanent—in fact, having a COO last more than a few years is rather uncommon. Thirty-three percent of COOs last for only one or two years, 18% last three or four years, another 18% last five to seven years, and only 11% stick with the company in that same role for over 11 years.)

If your COO no longer shares your vision for the company, no longer feels passionate about the goal, or the type of COO and roles you need them to fill changes as your future vision evolves, it’s time to move on. Herold says you’ll know when this time comes because your COO will stop enjoying the work as much and will feel more overwhelmed and stressed by their duties.

(Shortform note: Once you decide it’s time for the COO to move on, experts say there are a few more steps you need to take to ensure a smooth goodbye. For example, you must discuss the decision with the board—explain your decision and make sure they support it, discuss the COO’s separation package and get the board’s approval, and solidify a good reputation for yourself and the COO by focusing on the matter of misalignment rather than on the COO’s shortcomings.)