The Ongoing Challenges Facing Insurance Industry Leaders


COVID-19 has changed business as we know it. No one understands this more than those in the insurance and financial services sector. For an industry built on relationships, it has been an adjustment to conduct all business virtually — and that’s exactly what was discussed at the PIMA conference in June 2020.

The challenges industry leaders faced going into this pandemic won’t likely differ in a post-coronavirus world, and it’s important to understand more than just how to lead remote teams. You’ll also need to learn how to manage operations effectively as more disruptions come. Several company leaders provided insights into the most common challenges of being a leader today — and after COVID-19 passes — at the PIMA conference. Those challenges include the following:



If the pandemic has taught us anything, it’s how quickly corporations — and the people within them — can adapt to change. In a matter of weeks, entire departments switched to remote work without missing a beat. A recent survey from Lenovo found that 63% of workers feel even more productive at home than in a traditional workplace. 

This isn’t to say organizations won’t or shouldn’t go back to office settings after the coronavirus. Your company may decide to offer employees greater flexibility in working arrangements or have employees go back to the office full time. Whichever direction you choose isn’t the point — adaptability to recurring change is. This adaptability requires leaders and their teams to develop new skills continually and broaden their knowledge base.

Finding solutions to leadership challenges such as this can happen through:

  • Continuing education. People always need to learn. As knowledge broadens and grows, we tend to view things differently and find more creative ways to approach challenges. Outside-the-box thinking is key to innovation, after all. With PIMA, continuing education is easy: Members can access industry-specific articles, whitepapers, infographics, case studies, research, and many other resources to expand their skills and expertise.
  • Peer learning. While much of peer learning happens informally, this doesn’t mean you shouldn’t take opportunities to make peer-to-peer network connections. PIMA offers discussion forums and interest groups that allow for knowledge sharing and a chance to seek advice on myriad topics in the insurance industry.


Employee Engagement

As corporations return to some semblance of “business as usual,” leaders will still have the challenge of engaging employees. Even after the coronavirus passes, you’ll likely be leading remote and virtual teams on occasion.

Hiring the right talent can help, but you’ll also need to find ways to build cohesion within a team. If not, a lack of connection can quickly turn into a loss of motivation and productivity. Now is the perfect time to review employee engagement initiatives that will bring virtual — and nonvirtual — team members together:

  • Regular meetings. Schedule virtual team huddles at least once a week and open up discussions to more than just responsibilities. Employees need an opportunity to connect with one another and establish relationships with colleagues. Beyond that, have one-on-one meetings with employees to check in and help with struggles they may have.
  • Consistent communication. Keep your team in the know by providing a platform for regular communication — either with leadership or co-workers. Frequent communication doesn’t just ensure the timely completion of projects; it also shows a vested interest in your team’s success.
  • Recognition. Showing appreciation for a job well done has always been important, but it’s even more critical when leading remote and virtual teams. Make a point to share their accomplishments publicly.



During the pandemic, one of the biggest challenges of leading remote teams has been consistency in communication. At first, leaders were trying to find their own footing in the new virtual landscape, so correspondence was perfunctory at best. Team members were generally given only need-to-know information. This won’t be enough in the post-coronavirus world.

Going forward, how to lead remote teams effectively will involve greater transparency and clear, reliable communication on everything from daily tasks to the overall direction of the company. A collective clarity can help facilitate team cohesion and ease any lingering uncertainties.


Priority Management

The challenges of being a leader during COVID-19 have been plentiful, but one thing discussed during the PIMA conference was that many people struggled with managing priorities. When everything is thrown into question, it can be difficult to stick to a regular schedule — let alone prioritize what needs to be done throughout the day.

Like everything else on this list, priority management will be key to overcoming the challenges of leading a remote team now and in the future. Learning when to say no can be beneficial, but proper delegation is equally important.



It’s hard to ignore the importance of technology when leading remote and virtual teams. When the pandemic hit, many leaders found themselves relying on entirely new technologies to manage day-to-day responsibilities. This won’t likely change, and organizations should take it as a cue to continue investing resources in tech.

Video has certainly become a means of connecting remote employees, but your company should look at other tools to enable communication and bolster productivity virtually. Even when you do eventually return to the office, you may still need to maintain social distancing. You’ll likely be using new technology to keep operations running smoothly.

PIMA can help with a great deal of these challenges of leading remote teams — and help you find solutions to leadership challenges beyond this list. If you’d like to learn more about a PIMA membership or PIMA continuing education opportunities, contact us today.

Published on October 19, 2020.

PIMA® (Professional Insurance Marketing Association®) is a member-driven trade association focused exclusively on the group-sponsored benefits market