From Taboo Topics to Maintaining Boundaries: How Challenges Made these Senior Execs Better Leaders

As most executives who’ve reached a high level in their careers will tell you, avoiding failure at all costs isn’t what helped them get there.

The road to success is often paved with potholes. But, cliché though it is, the bumps, challenges and failures along the way all represent valuable learning opportunities. They certainly did for these leaders.

Below, we heard from seven senior executives about the biggest challenges they’ve faced in their careers, and how they grew from them.

1. Keeping up worker morale during a crisis

“The biggest challenge I have faced as a senior leader has been this pandemic,” Andres Lares, CEO and Managing Partner of the Shapiro Negotiations Institute, said. “I think it has required balancing the ability to be a motivator and cheerleader with also being realistic and transparent for my team, all while having concerns and challenges of my own.”

While solving for communication needs in a remote work environment has been a challenge, and one they’re continuing to work through, there have been other successes — including keeping a supportive culture intact.

“My successes were around supporting our team,” Lares said. “Psychologically, I was there, and financially we did not drop a single person’s compensation. We told them we would avoid that at all costs right from the get-go.”

2. Creating a market around a taboo topic

“The biggest challenge we faced as a company was navigating how to represent ourselves as a brand when we deal with such a ‘taboo’ topic,” Liz Eddy, Co-founder of Lantern, an end-of-life planning service, said. “Our users come to us when struggling with pain and grief, and we do our best to make sure we are a shining light during a dark time for them.”

Making empathy the cornerstone of her leadership approach, Eddy added, is what’s helped her navigate these challenges and dispel taboos the most.

“What helped me overcome this obstacle was harnessing my resilience and knowledge gained from my own experiences with grief,” she said. “We created a brand based on being a ‘knowledgeable friend,’ and we do our best to be as helpful as we can to each and every one of our users.”

3. Switching industries while mid-career

“Moving into speech recognition technology after spending years in politics was challenging,” Ottomatias Peura, today CMO of Speechly, said. “Both jobs were marketing and PR related, but understanding the technology and how to communicate its benefits to our clients took some work.”

To help, Peura turned to any educational resource in his field that he could get his hands on.

“In those early years, I poured myself into learning as much as I could about up-and-coming voice technologies,” he said. “I went well beyond our product to ensure I knew the terms of the industry, why our customers wanted this technology, and what our product specifically could offer them.”

4. Making a difficult termination decision

“I once worked for a very large and well-known company where I had to terminate my supervisor’s spouse without their permission or knowledge,” Jeff Goodwin, today Senior Director of Performance Marketing & e-Commerce at Orgain, said.

Although Goodwin added that not everyone will have to face this particular challenge in their career, the lesson he took away was a widely applicable one.

“For me, it was a great lesson on tackling hard situations head-on and not shying away from necessary but difficult decisions,” he said. “It will be fairly difficult to move upwards without accepting that.”

5. Maintaining boundaries as a manager

“The biggest challenge for me was learning that I need to set a distance between myself and the people I manage so that I can be considered an authority,” Petra Odak, Chief Marketing Officer at Better Proposals, said. “I’ve always tried to be friendly to everyone, which can be a challenge when you’re a manager. The people you manage start looking at you like a friend rather than their manager, and they relax too much.”

Being seen as approachable while also taken seriously as a manager can be a difficult combination to master, but it’s one worth pursuing.

“You really need to be an expert to get the right balance of being friendly and authoritative and unfortunately, it takes years to master this skill,” Odak added.

6. Hiring the right people

As Kevin Miller, founder and CEO of The Word Counter, put it, a “business is only as good as the people behind it,” which is why hiring decisions are so critical.

“A big challenge has been hiring the right people for the team,” Miller said. “Not only is finding the right match difficult, but keeping the team motivated and dedicated especially in times of isolation is also a hurdle to get through. Your organization and its longevity may very well be dependent on understanding who is a culture fit and who is not.”

7. Learning to receive difficult feedback

As a recent graduate working at a consulting firm, Jeff Havelka, today the CEO of Beyond Warehousing, received some feedback that wasn’t easy to hear.

“The first class of summer interns was starting in a few weeks, and I was certain that my application to be a summer mentor was a front-runner,” he recalled. “A consultant pulled me into his office one afternoon to discuss my application. I was told I would not be a mentor for the upcoming intern class. The feedback was that I was ‘cocky, condescending, and rough around the edges.’ He said this was not the company image they wanted the interns to perceive.”

Havelka was livid until, after some reflection, he realized they were right. He credits this experience as teaching him the importance of timely feedback, as well as being open to receiving that feedback.

“It is not always easy to hear, but it is a treasure to reflect on and take action to correct as needed,” he said.

---

Need help navigating a career challenge? Meet with an Ivy Exec Career Coach, or let us help you find a mentor!

---