Often there comes a time when the way we’ve been running our business no longer works for us. The growth of the business goes beyond our current role and we look outside to find a remedy. This could be simply adding your first actual employee or virtual partner or knowing that you need a leadership team – not just a leader. Whether you are a newly minted “solopreneur” or a chiseled veteran working on a company exit strategy, understanding the role of a second-in-command (2iC) will help make this transition a success.  

Recently, I've had some discussions with some very successful business owners about the second-in-command position, and ultimately, they've asked, "when do I know I need to add a 2iC?”

While it's never too early to start thinking about the future, these questions can help guide your way:

  1. Are you running your business or is your business running you?
  2. Are you losing out on sales or growth opportunities because you don’t have time to respond?
  3. Do you see the same problems in your business repeating themselves without any sign of resolution?
  4. Do you envision selling your business or passing it on to another generation?

Answering “yes” to one or more of these questions could be a sign that you may be ready to consider adding a second-in-command to your team.

Constantly feeling overwhelmed and even worse, unable to accomplish the necessary tasks to run your business is more than frustrating and tiring, it can be the initial signs of a quick ride to the bottom. In the beginning, it is common to have a succession of long days. But if this series turns into many months or years, it has become a habit – a habit, no doubt, where you are letting your business run you.

The old adage if your business isn’t growing then it’s dying is never more true than today. With the changing business climate, the ability to attract and keep new business as products and services change is paramount. I recently listened to an interview with Sara Blakely, the founder of Spanx, and she recounted her story of selling Fax machines door-to-door in the 1990’s as she was inventing her now famous body shaping apparel. At the time, fax machines were being sold at a premium and Blakely believes the challenge of selling a rather common product helped give her the tenacity in founding her own company. It did make me wonder with the rise of the digital platform exactly how many fax machines are now being sold 20 years later. Similarly, in your company, if you do not have the time to respond to new business or create new products or opportunities, your business could suffer a similar fate as the once coveted fax machine.

Most entrepreneurs start their business because they see a problem they can solve or an underserved need for a particular market. Ironically, that thinking often only applies to their customers. Like the cobbler’s children who have no shoes, many entrepreneurs struggle applying their outside thinking acumen internally. And because they are externally focused the internal mechanics can be dismissed or ignored often resulting in the Ground Hog Day effect where eventually you are solving the same problems over and over again.

Lastly, should you wish to sell your business some day or pass it on to another generation, there has to be a viable business – without you! John Warrillow, author of Built to Sell and whose Value Builder System has analyzed over 20,000 businesses and the characteristics that increase a business’s value, writes about the importance of the 2iC. In this article he shares that the quality of management teams, in general, may not sway an M&A team. Typically, the acquiring organization already has most of the functional components found on the management team. He says,

“If you're keen to build a great company over the coming decades, by all means hire a management team. If your goal, however, is to sell your business in the next couple of years, focus your resources on a solid 2iC that the acquirer can retain after an acquisition”

Thinking that a 2iC might be in your future? Here are the five steps to making that happen:

1.    Create Your Personal Inventory. Understand what you need to do, like to do and want to do for your business. For more on how to do this, read this recent blogpost.

2.    Find Your Complement. You can use the inventory you created in #1 to start your search. Additionally, most 2iC’s are typically internally focused and better than the CEO at some things including handling people. They are often not as interested in getting credit and more interested in getting things done. Additionally, you may want to consider one of the personality/thinking tests to help understand your style as well as those that work best with you.

3.    Start Practicing. With the awareness you develop with your Inventory, start segmenting tasks you are going to hand-off prior to having a 2iC in place. Knowing that you may no longer do a certain task may change the way you look at the task – is this necessary, can I train someone, what results am I really looking for? Also ask, “Is there something that I’ve always wanted to do but haven’t had the time?” Having a reward to replace the habit helps create a successful transition.

4.    Create Ground Rules. As a solopreneur or a solo-leader, we can make it up as we go along. Adding another person into your methodology can be tricky. While I often tell the CEO to avoid micromanaging, it is just as common to let go too much, too soon. Be clear on what you expect from your 2iC, and if you don’t have it completely worked out yet, develop the ground rules together. Understanding what isn't defined can just be as valuable as knowing what is.

5.    Communicate. John Kotter, in Leading Change says most leaders under communicate by a factor of 10-1,000. The importance of creating a regular communication plan is critical. The initial time together to create understanding and a common platform can pay off later as you want your 2iC to be able to stand in your stead as the business grows – both internally and externally.

In the end, most entrepreneurs start their business because they have a great idea or product they believe can make a difference. But inherent in this is also the desire to control their destiny and have a better life – both personally and professionally. Having a second-in-command in place can be one step closer to making that happen.

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