Five Scariest Moments for a Small Business CEO

Halloween has always been one of my favorite times of the year. I can remember as a kid dressing up and trying my hardest to scare people as we walked our neighborhood gathering treats. It was fun to frighten others and also to feel frightened myself from time to time.

As a small business owner, I’ve had more than my share of scary moments. The first day in business was always a frightening 24 hours. Facing Hurricane Andrew was as scary an experience as I can ever remember. Closing a business sale was always nerve-wracking.

What about you? Are you ever scared as CEO of your business?

Here are five of the scariest moments for a small business owner that I can think of, along with one strategy to address each one and ease the fear.


Fear #1. Losing a key employee.

The labor market is as tight today as it’s ever been in modern history. The national economy is at full employment and small businesses are finding it increasingly difficult to find and retain top talent. The fear of losing a star employee keeps many small business CEOs up at night. As a result, many companies are employing a variety of strategies aimed at retaining key talent, including financial incentives, enhanced employee benefits, and opportunities for professional development.

Strategy: Stay Interviews.

This simple idea gained traction several years ago. After the first 30 days of a new hire’s employment, schedule a meeting and ask them a very simple question: “What would it take for you to stay?” If a new employee is thinking of leaving, it’s typically about one month into their employment. Perfect time for the business owner or manager to make sure everything is okay.

Fear #2. Losing an important customer.

We work hard to gain new business and we dread the thought of losing a customer. And yet it happens. Sometimes small businesses devote much more energy and resources to finding new business than retaining their existing clients. “Churn” is one of my least favorite words.

Strategy: Net Promoter Score (NPS).

As described in great detail in the best-selling book The Ultimate Question 2.0 by Fred Reichheld, the Net Promoter Score is a great method for measuring customer service. Most Fortune 1000 companies have used it for years and it is now slowly trickling down to small businesses. NPS is an excellent early indicator of customer churn. Just asking your customers a simple question calculates it, “On a scale of 1-10, what is the likelihood that you would refer a friend or colleague to do business with us?”

Fear #3. Cyber Attack

“Cybersecurity is a silent killer. It can shut you down like nothing else.” – Joe Galvin, Chief Research Officer, Vistage International.

Cyber attack is a relatively new fear for small business operators. In a recent Vistage survey, 62% of CEOs do not currently have an active cybersecurity strategy in place. Every day, small businesses hit by cyber-attacks are losing data, cash, customer records, employee information, and employee/customer trust.

Strategy: A Layered Defense

1) strong cybersecurity (test yours using a reputable tool such as the Cybersecurity Framework). 2) Proper employee policies and procedures that will lessen and possibly prevent an attack. 3) Cyber Insurance.

Fear #4. Running Out of Cash

Every small business owner should fear running out of cash. Why? Because it’s game over when it happens. A wide variety of negative events are recoverable, such as losing a key customer or a high-performing employee. It is hard to recover from running out of cash. It’s similar to running out of oil in a car engine. Very few engines survive that circumstance.

Strategy: Calculate Your Working Capital Requirements

One way to prevent your business from running out of cash is to calculate the amount you need to prevent this from happening. In financial terms, calculate your Working Capital Requirements (WCR):

WCR = Cash Conversion Cycle (CCC) = (Days Receivable + Days Inventory – Days Payable) x Average Daily Sales (12 months revenue/360)

Example: DR = 40 days… DI = 60 days… DP= 45 days… ADS = $3000

WCR = (40+60-45) x $3000 = $165,000

In this example, your business needs to have ready access to approximately $165,000. This would include cash in the bank, a line of credit, credit cards, etc.

Fear #5. No Exit Strategy

Some small business owners long for the day they can exit their business. Many others are the opposite. They lie awake at night in fear of it. How will it happen? Death? Employee rebellion? Business failure? Research shows that over 50% of small business owners exit their businesses involuntarily.

There is much preparation in starting a new business and very little planning involved in exiting that same business. As a result, many business owners end up with much less on the way out than they deserve.

Strategy: Read Dance in the End Zone

Several years ago, author and Vistage speaker Patrick Ungashick wrote a very good book on this topic titled Dance in the End Zone. In the book, Ungashick outlines seven (7) questions to answer in exit planning. The first question is “when?”. The second question is “how?”. Completion of the book will get you started on your exit plan.

Happy Halloween!