Is It Time to Hire a Second-in-Command?

Business owners do it all—and frequently burn out doing so. Hiring someone to handle operations might just be the solution you need.
August 23, 2012

For many small-business owners one of the biggest upsides to the long days and sleepless nights is the opportunity to be the boss and run the show. But, there comes a time as the boss, when you need to delegate responsibilities. Having an effective number two, someone in charge of the daily operations, can ease the burden, provide stability for your company and make you a better business owner.

Denise Stern, founder of Let Mommy Sleep, Washington D.C.’s first and only baby nurse agency providing overnight care and parent education, knew it was time to start delegating her responsibilities when she became overwhelmed with the substantial growth of her new business. In just two years, Stern saw 400 percent growth and began struggling to handle the operational duties that keep a successful business running. “I knew I had to hire a second-in-command when I was too busy to consider hiring a second-in-command,” she recalls. “The tipping point was when my billings were falling behind and I was worried that I would not make payroll, even though we had many clients.”

The Viscous Cycle of Business Ownership

Stern, like many small business owners who are also CEOs, couldn’t seem to get herself out of the cycle of taking care of every aspect of her business. “I was afraid my business would suffer if I took the time and resources to hire help,” she adds.  Instead of her business suffering, however, it was Stern who personally felt the brunt of the chaos.

Today, Stern is still the voice of Let Mommy Sleep, where her sales, marketing and promotional skills are being used to grow the business. She has since delegated all the bookkeeping, employee on-boarding, and some of the daily communications with customers, to her COO.

Keep an Open Mind

Like Stern, CJ Scarlet of Roving Coach International credits her chief of staff for helping her business run smoothly and effectively. “Sunita Shouse joined our team in 2010 and plays an integral role in every facet of the company, from operations to sales to account management to marketing,” says Scarlet.

But, Scarlet did not set out to hire a COO. It was by chance when an intriguing lunch conversation opened her eyes to the possibility that her business could benefit from the business expertise that Shouse possessed.

“My two partners and I have experience as coaches, marketers and in HR, but no operations experience. We floundered through our first year in business and it wasn’t until I learned more about Sunita’s operations background that I realized it was exactly what was missing from our skill set.”

Make the Change

So, how do you know you're hiring or delegating your responsibilities to the right person? It’s not unlike hiring any integral part of your team. If you’re working alone, or are used to doing everything yourself, it may be time to concede that you can’t do it all. This, perhaps, is the most difficult task of adding a second-in-command.

To help Stern overcome this hurdle, she reflected on the repercussions affecting her most important asset—herself. “Doing all the tasks yourself in a small business is a surefire road to burnout,” she says. “Protecting your most valuable asset—you—should be a priority.”

Both Scarlet and Stern looked at hiring a COO as an investment, knowing it was something they each needed in order for their businesses to grow. “Find one as soon as you’re able,” Scarlet says. She also suggests considering alternative payment arrangements if you don’t believe you can afford to hire a COO. “Don’t think you can’t afford one! If you think creatively, you’ll be surprised at what you can arrange.”

Scarlet suggested offering stock options, deferred compensation, flexible work hours or generous benefits to help offset the payroll. “The possibilities are only limited by your imagination,” she adds.

Finding the Right Fit

Another obstacle many small-business owners face is finding a COO whose personality and business savvy complements, and meshes, with their own. You need to find someone who you not only get along with, but can become an extension of your business. “This will likely be your most close and personal business relationship, so choose wisely,” advises Scarlet. “Look not only for a cultural fit but for a personality fit. You must truly like and respect this person because you will need to trust them with intimate business details.”

In addition, you will need to be able to trust your COO with running your business in a way that facilitates growth and advancement. They will need the ability to see the big picture and understand the processes to help you grow.

For Scarlet, the day Sunita took the reins was a day of liberation and freedom. “One day, she put her hand on my arm and said firmly, ‘Let me do that for you.’ I finally got that I didn’t have to do it all myself.”

Angela Stringfellow is a PR and MarComm Consultant and Social Media Strategist offering full-circle marketing solutions to businesses. Angela blogs via