Matters of perspective: Generational viewpoints

In a breakout session at the 2024 BenefitsPRO Broker Expo, a jam-packed panel including, Susan Combs, CEO, Combs & Company; Eugene Starks, Partner, Acuity Group; Sue Wakamoto-Lee, director of business development, Advanced Benefit Consulting and Insurance Services; Jenny Weaver, national partnership specialist, PES; Jessica Brooks-Woods, CEO, NABIP; Marlin Woods, executive coach, The Woods Plan; and Sims Tillirson, SVP, sales & broker partnerships, BLUE RAVEN actuarial discussed their challenges, backgrounds, stereotypes, opportunities, and the future.

While discussing what dress code was like for male boomers back in the day, Eugene Starks said “When I got into my professional job, it was always coat and tie… I could be in my office and take my coat off, but if I got up to walk around I had to put my coat back on.” Sue Wakamoto-Lee, who is from the baby bomber generation, agreed and emphasized the no open-toe shoe policies she experience.

“Especially when it comes to women, a lot of times you see those trends shift when a women becomes in leadership,” added Susan Combs, who comes from Gen X. Combs shifted the conversation to talk about stereotypes of each generation, saying “When we start talking about different companies and different cultures, a lot of your past and how you are raised come into play.”

Sims Tillirson, a millennial, shared that he got his first “real job” at 22. Since then, he has been a part of seven companies which plays into the millennial stereotype of job-hopping. However, on the other hand, Wakamoto-Lee shared that she has had 17 careers and has been fired five times.

Related: Employee mental health challenges remain after the pandemic, research finds

The conversation shifts once more to discuss prospect. “It was still walking in the door, and a lot of times the owners were just there. Since COVID, I’ve realized owners aren’t there anymore, so now it’s a little different,” millennial Jenny Weaver shared. Marlin woods (Gen X) shared that he was cold calling at the beginning of his career, but now he doesn’t prospect at all. His business comes strictly from word of mouth.

“Career fairs were a big deal, setting up booths and hand-shaking… but now it’s centers of influence and relationships. LinkedIn is very active for me and I’ve been able to develop authentic relationships to that platform,” said Jessica Brooks-Woods.

To finish off the session, Combs asked everyone to describe success in one word to name something challenging for their generations:

Woods (Gen X): “Responsibility and the challenge is to unlearn error.”

Weaver (millennial): “Journey and it’s challenging not to be put in a box.”

Starks (boomer): “Warm convivial gatherings, meaning intimate time with people. The challenge for my generation is letting go.”

Brooks-Woods (millennial/Gen X): “Impact and the challenge is burnout.”

Wakamoto-Lee (boomer): “I’ll let you know when I’m there. The biggest challenge is to stop being so stubborn.”

Tillirson (millennial): “Presence, like having the ability to have control over my time to be present with the people I’m with. The challenge is working to heal generational trauma while trying to raise kids ourselves.”

Combs (Gen X): “Tenacity or the ability to find the answer. The most challenging is finding balance and that blend.”