16 business leaders on overcoming their ‘scariest’ leadership challenge

Industry Insights

Ideas to Inspire

16 business leaders on overcoming their ‘scariest’ leadership challenge

Every career comes with highs and lows, but when one is in a leadership position, the lows can seem especially daunting. After all, you have a team of people depending on you and turning to you for guidance; it can be hard to admit you’re going through a rough patch — and that you’re scared.

Business Journals

Part of running a business is overcoming such obstacles to grow your company and improve your leadership skills. It’s important to remember that you’re not alone in these struggles. Below, 16 members of Business Journals Leadership Trust share the “scariest” business situation they’ve ever faced and how they successfully navigated it.

1. The 2008 recession
Not long after I purchased LAN Systems in 2008, the Great Recession hit. Later in the year, the stock market plummeted and we experienced the worst recession of my lifetime. My goals for modernizing the company were greatly delayed. How did LAN weather the storm? In a word, tenacity. I knew the plan was sound, and I worked it each day with changes that reflected the tough times. – Mary Hester, LAN Systems

2. The 2013 federal government shutdown
In 2013, the federal government shut down. Many IT consultants were trying to preserve income from traditional sources, too. But we knew if we were going to survive, we’d have to be cloud-forward. So, we shifted to Office 365 early while others stayed focused on Enterprise SharePoint. The result: We’re ahead of other firms in our industry and are offering better support models and prices. – Thomas Carpe, Liquid Mercury Solutions

3. Losing my corporate job
The 2008 downturn produced job cuts and my first experience with job loss. I turned fear into opportunity by identifying areas where I could provide critical services at a fraction of my salary while also using my skills to help other businesses. I presented my employer with a solution to help us both, which became the cornerstone of launching my business. – Robert Wolf, CREIS, LLC

4. Deciding whether to file for bankruptcy
There was a point where filing for bankruptcy was an option on the table. Weathering the storm is an experience that hones a leader, but to navigate it successfully, you must be willing to make the difficult decisions and always keep a positive mindset. But the most important thing of all is to never stop hustling. You have the power to change your position and successfully overcome your situation. – Jack Smith, Fortuna Business Management Consulting

5. Losing our biggest client
We lost our largest client. We had to cut salaries and execute layoffs for the first time in my company’s history. We rebounded by networking and redoubling our efforts in new business while working hard to keep our current clients happy. It took hard work — the usual answer to many of the challenges that life can throw at you! – Carter Keith, 31,000 FT.

6. Launching a software company with no funding
Years back I risked everything and started to build software, as opposed to running a service company. I had no large seed funds, no friends and family help, and definitely no investors — just me. Despite everything, I came out strong and never looked back. It has allowed us to scale internationally and compete against giant companies. A leap of faith is all it takes. You never know if you might just make it. – Solomon Thimothy, OneIMS

7. My business partner backing out
My entrepreneurial journey started off very rough, with my business partner backing out less than a week into our new venture. The original strategy had to be thrown out and a new plan had to be formulated — very quickly. When you are facing challenges and can’t see your way forward, take a break, ask for directions and plot a new course. Your tenacity and persistence will pay off. – Jared Knisley, Fizen Technology

8. Periods of uncertain sales and revenue
All businesses are based on continuous sales and revenue, but these numbers continuously fluctuate. This uncertainty is a constant challenge any business faces. Adjusting operations according to various levels of business ensures you are nimble and prepared for anything that comes your way without waiting until it’s too late to take action. – Jessica Hawthorne-Castro, Hawthorne Advertising

9. Growing the team for a client that later liquidated
We expanded our team for a new major client. We didn’t realize they were so emphatic about headcount because they were on their way to liquidation 18 months later. We found ourselves outsized for our income. However, our pipeline is very long, so we were reluctant to abruptly right-size. We cut costs, kept everyone we’d hired but didn’t replace folks who left, and grew sales enough pre-Covid-19 to expand our team again. – Billy Hodges, Digital Filaments

10. Relocating right after starting out
Honestly, the scariest thing is starting out. I started right when the market tanked and I thought it might be the end, but I made the crucial decision to move my operation to Kansas City. Looking back now, it was the perfect decision. Kansas City is a big construction city, and that was right in our wheelhouse. Make sure that you adapt to the market — don’t stagnate. – Brandy McCombs, IBC

11. Losing face-time with customers due to an accident
I had a skiing accident and was out of the office for four months. I was not able to be in front of customers, which affected sales as well as some of the contracts we already had. We were very dependent on one customer, which we lost. We got better at working remotely and made sure no customer comprised more than 15% of the business. We kept going, but we no longer depend on just one customer or one person. – Sergio Retamal, Global4PL

12. Not being able to make payroll
When you have people relying on your dream for their livelihood, it requires you to improve your billing procedures, engage clients who aren’t paying on time and reexamine your contracting and billing processes. Most of the time these strategies have worked, but I’ve also had to dip into personal finances when in a pinch to make sure our team is taken care of first. – Liz Wooten-Reschke, Connect For More

13. Eliminating a business partner
The scariest situation I ever faced was eliminating part of a partnership. We were faced with a bad economy and a partner that was not aligned. Several of us discussed it, and a decision was made. To this day, I regret not discussing it openly with everyone involved. I’ve repaired the affected friendships and we all came to agreeable terms, but I still kick myself for the way I handled it. – Brent Foley, TRIAD Architects

14. Facing a temporary shutdown
In April of this year, we were forced to pause our operations due to the coronavirus. This was devastating for our employees, most of whom are hourly workers. We chose to put our people first and continued to pay them a portion of their usual average pay. By caring for those who care for our business, we helped them through a scary time and got back up and running faster the following month. – Aric Burke, Atlas Healthcare Partners

15. The shrinking Covid-19 economy
In February 2020, my company was poised to double in size over the course of the year. When Covid-19 struck, my company was faced with the big threat of the economy shrinking and our clients losing business. We handled the situation well mostly because we had prepared for a 2020 recession 12 months prior. We made sure we had cash available, operated very lean and focused on helping our existing clients navigate the pandemic. – Sanjay Jupudi, Qentelli

16. Taking that first step
My scariest situation was simply getting started and taking that first step in creating positive momentum. When you start a new business in the highly competitive health care field, you need to establish contacts and obtain business quickly, because you have responsibilities that go beyond yourself. That can be paralyzing, but persistence and a positive attitude are the keys to success. – Phil Gibson, CatylystOne

Drop us a note to explore how You can future proof your brand and business