Decisions that Define: 6 Leaders Share Their Toughest Decisions—and the Lessons Learned

Almost every business leader who has been around a while can point to a “fork-in-the-road” decision that—for good or bad—led to monumental change for their companies or themselves personally.   

For example, look at the breakfast cereal market in 1929. When the Great Depression hit, industry leader Post opted to hunker down and stop advertising. But the executives at second-place Kellogg saw an opportunity and poured millions into new ad campaigns. Soon, “Snap! Crackle! Pop!” entered the cultural lexicon and Kellogg jumped up to become the No. 1 cereal brand—a position it still holds today.

These type of pivotal business decisions also provide important lessons for C-suite leaders of the future. That’s why the SHRM Executive Network asked a group of executives to share their thorniest business decisions and the lessons they learned that still stick with them today.

1. To Embrace or Hide Mistakes

Trent Griffin-Braaf, CEO and Founder of Tech Valley Shuttle, a transportation company in Albany, N.Y.

The decision: Early in his career, when Griffin-Braaf was seeking an entry-level position at a hotel, he had to decide whether or not to tell the hiring manager that he’d served a 12-year prison sentence.   

“I had to make a decision to either be very transparent with my story … or act as if it never happened and never share that portion of my life with the business community,” Griffin-Braaf says.

There was a decent chance the manager wouldn’t check too closely for an entry-level hotel post, but Griffin-Braaf opted to come clean.

“Although I had made a mistake as a youth, I didn't believe that defined me,” he says. “And I learned that if someone didn't want to do business with me because of a mistake or being formerly incarcerated, I also didn't want to do business with them.”

The lesson learned: From that hiring manager’s early acceptance. Griffin-Braaf learned that he was always going to lead with his full story. He ended up building two award-winning transportation companies by taking the above-board approach—and encouraging others.

“It was amazing,” he says. “I had a lot of people reach out to me and say how inspired they were by my story. It helped do away with some of the bias and stigmas associated with people who’ve been to prison.”

Today Griffin-Braaf regularly shares his “Felon to Forbes” story by speaking at prisons about reconnecting to society and the workplace.

“We should never be ashamed, embarrassed or afraid to share our personal story,” he says. “You just never know how you can help others by telling it straight.”

2. To Stay Small or Go Big

John Peebles, CEO of Administrate, an enterprise training operations platform in Edinburgh, Scotland

The decision: In 2019, Peebles led the team that decided to pivot Administrate away from the small-to-midsize business market the company had been successfully running. Now, the firm would instead entirely target large, multinational companies.

“This was difficult because we had built a good business with strong metrics that were working and scaling. But it wasn’t a great business,” Peebles says. “One of our customers was growing rapidly and eventually went public. Through this fast-paced growth, we saw firsthand how much more value we could bring to larger, more complex companies.”

The decision reminded Peebles of a basketball coach who, at halftime of the championship game, told his team the usual strategy wasn’t working. Instead, the coach chucked the playbook and wanted to try something new.

“We knew it would be blowing up everything we’d done for five years and starting over,” Peebles adds. “That is always super difficult.”

The lesson learned: Peebles says it can be tempting to stick with something that is working fine and making money, even if it’s not “great.”

“The need to constantly evaluate and re-evaluate every aspect of your business is essential and never ends,” he says. “Sometimes, the outcome of that exercise will be painful, and sometimes, it will be super challenging. But ultimately, that’s what leadership means.”

3. To Use Layoffs to Save the Company

Joe Camberato, CEO at National Business Capital, a fintech marketplace lending company in Hauppauge, N.Y.

The decision: When the COVID-19 pandemic hit and businesses were shuttered, Camberato’s company was left hanging.

“Our lifeline, our supply chain, is money, and it essentially came to a standstill,” Camberato says. “Everyone had access to free government funding, making our services less appealing. Overnight, our cash flow stopped, and I found myself in the midst of a storm. Each passing week meant we were hemorrhaging money.”

The dilemma was stark: Bleed cash and hope for a miraculous recovery, or make the gut-wrenching decision to lay off a significant portion of his 100 employees. He opted for the latter.

“It was a painful choice, and it unfolded during one of the most challenging times the world has ever faced,” he recalls. “I remember those days vividly; they were sleepless and agonizing."

The lesson learned: “First and foremost, the experience underscored the importance of honesty, transparency, vulnerability and compassion,” he says. “Throughout the ordeal, I remained transparent with my team about what was happening and the reasoning behind my decisions. That authenticity made a major impact. People value honesty.”

The experience drove home the point that CEOs must do what’s right for their business but never forget the human side of the business.

“Tough decisions are an inevitable part of business, and when they are the right decisions, they must be made,” Camberato adds. “But being sensitive and humane in how those decisions are communicated is equally important.”

4. To Stay Home or Go Global

Joan Denizot, founder and CEO of Zize Bikes, a bicycle manufacturer based in Kingsport, Tenn.

The decision: Zize Bikes was an established brand in the U.S. when Denizot faced the decision of expanding into international markets. That held the promise of increased revenue, but also meant dealing with unfamiliar regulations, cultural differences and market dynamics.

“The reason it was particularly tough was that it required a significant investment of resources, time and effort, and it was fraught with risks and uncertainties,” Denizot recalls. “The decision required careful consideration of whether our products would resonate with a global
audience, the logistics of distribution and the financial implications.”

The lesson learned: The company ultimately succeeded in their global reach, and the most valuable lesson Denizot learned was the importance of thorough market research and strategic planning.

“We realized that entering international markets without a deep understanding of the local
nuances and preferences could lead to failure,” she says. “It taught us the significance of building strong relationships with local partners and understanding the competitive landscape.”

As a C-suite executive, Denizot also learned the importance of adaptability and the ability to pivot company strategies based on real-time feedback and data. “In this case, we had to be
agile and adjust our marketing and product offerings to better suit the international market.”

5. To Walk Away and Reinvent Yourself Elsewhere

Edouard Thoumyre, managing partner at ACCUR Recruiting Services in Miami.

The decision: Thoumyre left a promising career in France and his two master’s degrees at French schools to move to the United States and launch a business from scratch. Today the professional executive recruiting firm he founded works with high-profile clients like Hermes, L’Oréal, Mars and Monster Energy.

“This was a significant risk, as I was entering a field I didn't know, focusing on industries I had never worked in, in a market I was unfamiliar with, and using English, a language I was still mastering,” Thoumyre says.

The challenge was turning apparent disadvantages into advantages.

“With my French background, I observed that many French companies in Miami were in the luxury goods industry,” he recalls. “These brands were deeply connected to France’s image and culture. By introducing myself and my services to French decision-makers or those in French companies in Miami, I was able to quickly build trust and rapport.”

This approach paid off and, within a year, ACCUR had signed most of the French luxury goods companies in Miami.

The lesson learned: Thoumyre learned about the power of embracing and leveraging one’s unique background and differences.

“Instead of viewing my foreignness and unfamiliarity with the industry as setbacks, I turned them into assets that set me apart in the market,” he says. “This mindset has been
instrumental in the growth and success of my company.”

6. To Shift Strategy and Have a Plan ‘B’

Amy Spurling, co-founder and CEO at Compt, a company perks and stipends management advisory firm in Boston.

The decision: In a prior job when Spurling was hired as CFO, she quickly found out that the company was in the process of being acquired. The company had solely concentrated its efforts on this deal, leaving it with limited cash reserves and no backup plans. When the market crashed in 2008, the deal fell through. With cash dwindling and facing deep cuts across the organization, Spurling and the CEO had to make the toughest of calls for senior executives.

“We eliminated an entire division that focused on a project that had just started because the market wasn't viable,” she recalls. As a result, the company had to lay off several employees who it had recently hired.

The lesson learned: Spurling realized that the decision to eliminate the division and cut staff quickly was correct because it ultimately prevented a more drawn-out, agonizing process that could have spread across the entire company.

“I learned never to put all your eggs in one basket,” Spurling says. “It seems obvious now, but having multiple game plans is a lifesaver. Preparing for multiple scenarios, even it entails more work, not only offers a safety net but also increases the chances of success.

“Looking back, these lessons may seem like Business 101,” she adds. “But living them in real-time, absorbing them, and emerging as a better leader is a completely different narrative.”

Brian O'Connell is a freelance writer based in Bucks County, Pa. A former Wall Street trader, he is the author of the books CNBC Creating Wealth (John Wiley & Sons, 2001) and The Career Survival Guide (McGraw Hill, 2004).