Second in Command, First in Line

This article is the 2022 Golden Quill Award winner!

Branch manager, general manager, operations manager, director, vice president of this, assistant of that. These are all titles synonymous with being the second in command of an organization. They are also a list of titles I have held throughout my lifetime, whether they were paid or volunteer positions. In short, I have made a living from running other people’s businesses and organizations. Throughout my journey, there have been many lessons learned from those seats. And while some were harder than others, there is a definite pattern to the behavioral attributes that lead to successful outcomes.

Today’s business environment is a bounty of mergers, acquisitions, and generational succession. Whether business owners are looking to maximize the market value of their company or set it up for future generations to take over, the demand for top performers in these second-in-command positions is starting to become overwhelming. There isn’t a week that goes by that I don’t have a conversation with a current, past, or prospective client about hiring a right-hand man or woman to run their business.

The conversations generally center around the skills and competencies required of these individuals, how to find them, and how to compensate them. In part, this was the original motivation for a three-part series of articles I wrote in 2015 titled “The Ultimate Test of Loyalty.” This series focused on building a strong case for the why and how of the second-in-command position while addressing the underlying issue of trust between them and the owner. In reflection, it adequately served the purpose of persuading owners of the need for this position, but it missed the mark on providing practical information for what it really takes to run someone else’s business.

Looking back on my own career and having observed the performance of dozens of other successful individuals in these roles over the years, I can surmise that the behavioral attributes necessary to be successful fall into a general theme of being “first in line.” This begins with being first in line to listen to the owner.

Entrepreneurs have A LOT on their minds, and most of them like to be heard. This makes listening a necessary attribute of any lieutenant. Be it criticism, complaints, excitement, or overzealous optimism, owners need someone to go to with the confidence of a level head. This provides them with both a sounding board and a filter.

The sounding board serves as a way for the owner to get things off their chest without going directly to the staff and possibly exciting a situation, which may not be warranted.

The filter, on the other hand, provides focus and protection when it comes to the never-ending stream of new ideas rolling around in the owner’s mind. These could be new products, services, policies, practices, procedures, or a host of other things related or unrelated to the business. An effective right-hand person has the wherewithal to serve as an oversized catcher’s mitt for a barrage of pitches thrown at unpredictable rates of speed and with questionable degrees of accuracy. Deciding which of these ideas to catch and act on and which to let go involves the uncanny ability to prioritize fast-moving objects quickly and with a sharp eye. It also takes a skilled communicator to challenge ideas and concepts that are not yet thoroughly vetted.

This is where the groundwork for an effective relationship between the owner and lieutenant is born. The ability to have authentic and candid conversations while still maintaining a sense of humor is imperative. This is by far the most stressful part of the job. However, it could also be considered the most important because the vision and creativity of the owner, when harnessed correctly, is a necessary component to the growth of any organization.

This leads to being first in line to try new things. While this flies in the face of instinctual survival strategies (rarely do you see the dominant animal take the lead on a trail), it does embody an attitude necessary to lead by example. Often this encompasses new business initiatives, processes, or projects that have never before been attempted. It could be something as simple as using a new software program or as complex as managing a project the company has no experience with. Either way, being the second in command means going first and never ever asking the employees to do something you wouldn’t be willing to do yourself.

Being first in line to try new things comes with a high degree of risk. The likelihood of failure is always looming with each new action or decision, often feeling like mission impossible. The tendency to polish up your résumé as a contingency plan can be more than tempting. However, this is where trust and respect play a critical role in the relationship with the owner. If these elements are healthy, there should be an understood freedom to fail, within reason. When established, this takes some of the pressure off and allows the Lieutenant to focus on the task at hand. The results are surprisingly positive for the entire organization, leading to greater degrees of latitude and creativity among the staff.

Along with trying new things comes being first in line to accept responsibility. I have often joked with my clients and colleagues by proclaiming, “Scapegoat is right next to guinea pig” on the job description. The reality of this statement is that the chief operator must be willing to accept responsibility for any and all actions of the organization because they are either a direct or indirect result of the position’s influence. This includes decisions made by the owner. While we may not always agree with them, the decisions must be supported and executed diligently throughout lower levels in the organization.

If there is any sense that the owner and the second in command are not on the same page, the fallout can be ugly.

Accountability is one of the most overused terms in business today. It gets thrown around as a general excuse for why things don’t get done, as though we can somehow influence employee behavior simply by telling them to be more accountable. Or worse yet, force them to be accountable by implementing more stringent policies and reporting structures. Accountability starts at the top. Or in this case, close to it. Employee behavior is most effectively influenced by the actions of the leaders in the organization. As the second in command, this begins and ends with modeling accountability by understanding and accepting these responsibilities without exception.

As if this all wasn’t enough to consider, the last attribute is to be first in line to sacrifice. Don’t get me wrong, operating as the legs of an organization and not always the face can have its advantages. You get to play with someone else’s money and take risks you may not necessarily take with your own equity. You aren’t the one paying the tax bill at the end of a good year. And creditors don’t look for your name on the personal guarantee line. This is not to suggest that the job comes without sacrifice; it just looks different.

Most of the sacrifice in the second-in-command position is done unknowingly to others—including the owner.

Employees must be taken care of first, even if that means sacrificing compensation or benefits to stick to the budget. Difficult projects or activities must be handled to mitigate the risk of tying up key producers with the burdens of those assignments. This is all done to uphold a bargain between the owner and their Lieutenant.

The bargain is a simple deal. The owner entrusts their right-hand person with an investment. In exchange, they bring the owner a return on that investment. But here’s the catch: the benefit of playing with someone else’s bank account also comes with an incomprehensible burden only a few can relate to. You see, the return on the investment is not just anticipated or expected; it’s an obligatory responsibility of the position. Without question, this is the most burdensome part of being the second in command and anyone who tells you otherwise doesn’t have the respect they should for the bargain.

Given all the above, you might be wondering why anyone would want this job, and you see why some would consider the position to be a unicorn. Fortunately, they do exist and there are many who not only want the job but who view it as a highly prized pinnacle of their career. These operators may be few in number, but they are worthy of pursuit, and the positive impact they can have on an organization poised for growth is undeniable. The key to making it work for your company is recognizing the individuals who possess these attributes and putting them first in line.