6 ‘Do-Over’ Opportunities C-Level Executives Wish They Had

By Brian O'Connell September 1, 2020
6 ‘Do-Over’ Opportunities C-Level Executives Wish They Had

​In golf, getting a second chance to hit the same shot without penalty is known as a "mulligan."

For executives, the notion of getting a "do over" has its appeal—and for good reason.

  • Would former Apple CEO John Scully have fired company founder Steve Jobs if he had a second bite at the apple?
  • Given a mulligan, would George Westinghouse have alienated Nikola Tesla by changing the terms of his contract, thus losing one of history's foremost inventors?
  • Would Dick Rowe of Decca Records have turned down The Beatles, the most successful recording group in rock music history, if he'd had a second chance?

Unfortunately, management mistakes of that magnitude aren't reversible. Often, CEOs and business owners must own up to big blunders of their own.

We asked CEOs and business leaders to describe bad decisions they've made in hopes of teaching future leaders the types of mistakes they can't afford to make.

1. Being too loyal to staff at the expense of the company.

Casey Halloran, co-founder and CEO of Namu Travel, a Costa Rica-based travel agency, said his biggest regret on the executive perch was holding on to people for too long out of loyalty.

"This seems to be a fairly common mistake, especially for leaders who really care about their staff," Halloran said. "As company leaders, we all know when there's a person who just isn't contributing, is riding on past accomplishments or is burned out."

Halloran, who now oversees a company with over 100 team members and $25 million in revenue, said it's difficult to make a job-ending decision that everybody knows will hurt and that can end decades-long relationships. Still, it's the best thing for all sides.

"In my view, letting go of people you really care for but aren't doing the job might be the hardest thing as a business leader," he noted. "I didn't do so early on and paid the price. What I have learned is to remove [such] employees sooner, before it becomes so painful."

2. Overlooking "important introductions."

For Julia Enthoven, co-founder and CEO of Kapwing, a San Francisco-based video and imaging collaboration company, her biggest mistake as a company leader was something she didn't do.

"In the early days of growing the company, I felt overwhelmed by all the things I needed to do to raise money, hire and grow the business," she said. "However, I made the mistake several times of not being responsive to an important introduction, and that was a big mistake."

Enthoven said she was introduced to an "incredibly kind and successful former CEO and advisor," but she didn't nurture the relationship and was slow to respond when he reached out. "I no longer have a close relationship with that person and wish I'd spent more time nurturing the mentorship early on."

The same thing happened when Enthoven had a shot at hiring one of the best engineers in her company's field but didn't follow through. "I was extremely busy with product development and felt like I didn't have time to invest in engaging with the engineer," she noted.

"Attracting great talent should always be your highest priority, and I regretted it later when that same candidate found another role at a different startup."

3. Not getting tough with company rules.

Michael Levitt, founder and chief burnout officer of The Breakfast Leadership Network, a San Diego-based media firm, says there were "plenty of do overs" he wished he could have from his corporate executive days.

Chief among them is being consistent in enforcing company rules and codes of conduct.

"Early on, I was a people pleaser as an executive and allowed staff to bend the rules in a few areas," he said. "This created an imbalance between team members and ultimately created an unhealthy climate in the organization. Given an opportunity to do it over again, I would have either rolled out flexible rules across the board or simply abided by the policies and procedures we already had in place."

Levitt also regrets not following the advice of leadership guru Tom Peters in "hiring slow and firing fast."

"I inherited an organization that had an average turnover of 80 percent of the team, and I did eventually reduce that turnover rate to 6 percent annually," he said. "Early on, however, there were toxic employees who were original hires who caused problems for the company. If I could have a do over, I would have terminated every one of them. They created a toxic environment and didn't perform as needed."

4. Not setting clear expectations.

Daniel Koffler, founder and CEO of New Frontiers, a New York City-based provider of education and social support services, started off with a small team and didn't have human resources support, nor a thoughtful effort to establish a mission statement and core values.

"We just ran hard and fast," Koffler said.

As the company grew, Koffler knew he had to add staff, and did so, but with no effort to establish a unified company culture that would resonate with all employees.

"We didn't spend the time to establish, clarify and repeatedly communicate our expectations of them from a culture perspective, let alone provide team members with clear and consistent guidelines on performance improvement," he said.

That led to dissension in the ranks and the need to fire toxic employees.
"That was the real tactical misstep," Koffler said. "I didn't see the importance of letting employees go before their disaffection leaked into the ranks. Instead, I chose the path of least resistance, ignored the dissension and let it fester."

Eventually, Koffler did cut the cord with problem workers.

"Once the team recognized that things improved afterward, we began to take more of a 'no one person is more important than the organization' approach," he said.

5. Taking on too much.

In her earlier career as a marketing and public relations agency owner, Kristin Marquet cut her teeth working as a public relations and branding professional with high-profile names like haute couture designer Samantha Giraud, celebrity fashion designer Nick Verreos and prestige hair care brand Briogeo. She also worked with big media brands like The Wall Street Journal and Glamour magazine.

Marquet found herself working long hours and taking her eye off other important life priorities.

"In the early stages of growing and scaling my first business, the biggest mistake I made was working more than 80 hours a week … to show off my achievement," she said. "I tried to manage all aspects of the business from business development to client work to marketing to finance. I was newly married, so my marriage sustained quite a bit of strain. When I look back at that time, I realize it was a big problem."

After a year of working tirelessly, she hired help and outsourced as the business grew. Doing so, she said, "enabled me to have a life outside of work."

More recently, Marquet launched Fem Founder, a company that helps women plan, launch and grow startups. In this new venture, working 80 hours a week won't be an option.

"As a former marketing agency owner and now a branding and business specialist, I've witnessed a number of younger CEOs spending every waking moment at work as a way to prove their loyalty to their team members, the board and other C-level executives," she said. "My advice is to do an efficient job during your regular work hours. Be productive and organized so you can have a life outside of work."

6. Ignoring advice from others.

John Howard, founder and CEO of Coupon Lawn, a consumer coupon code platform based in New York City, said mistakes are inevitable when it comes to running your business.

The trick, he says, is to learn from those mistakes.

"Early on, my biggest mistake was to ignore my team's advice and … being a self-centered person," he said. "I've always believed that I am capable of running my business without anyone helping me, so I ignored advice that could help my company."

Avoiding good advice from employees and business peers almost caused the downfall of Howard's business, and it hurt his relationships with the Coupon Lawn team.

"It created a lot of mistrust and affected the company's performance," he said. "I resolved the issue by increasingly opening my ears to suggestions and trying not to neglect my team's great ideas. I taught myself to trust my team and to trust [their] plans and ideas. Ultimately, any business leader has to avoid being self-centered for the sake of the company."

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's Creating Wealth and The Career Survival Guide.



Hire the best HR talent or advance your own career.


The PMQ teaches managers to lead effectively, giving HR more time to meet the demands of the workplace.

The PMQ teaches managers to lead effectively, giving HR more time to meet the demands of the workplace.

Discover PMQ


HR Daily Newsletter

News, trends and analysis, as well as breaking news alerts, to help HR professionals do their jobs better each business day.