Forging Stronger Inter-Generational Relationships for Company-Wide Success

by Rita E. Garwood May/June 2020

What does it take to attract and retain younger employees? Cara Silletto says it all comes down to relationships. When managers act like coaches and team members take the time to understand each other’s backstories and utilize each other’s strengths, authentic relationships are possible, and each member of the team can feel appreciated and valued.

Cara Silletto, MBA,
President & Chief Retention Officer,
Crescendo Strategies

This issue of Monitor celebrates the next generation of leaders in the equipment finance industry. These rising stars see the world in a fresh light, adapt to new technology quickly and challenge the status quo.

But what attracts younger employees to a workplace? Many believe young people want a fun environment with bring-your-pet to work days, ping pong tables and video game rooms, but Cara Silletto, president and chief retention officer of Crescendo Strategies, says the No. 1 draw for younger workers is great managers. These leaders communicate effectively, understand and appreciate their employees, and treat each member of their team like the complex human beings they are.

“They want to work for a boss who is more like a coach,” Silletto explains. “They want to have mentors who they look up to and trust, and they want to feel like they have an authentic, genuine relationship with those people.”

Silletto says the employer/employee relationship has shifted over the years. In the past, a sense of obligation tied workers and employers together. Employees showed up and completed their work and employers paid them accordingly. But in the 1990s, the internet and globalization changed everything.

As companies began outsourcing and offshoring, U.S. employees experienced more layoffs and less stability. “That’s when the employer/employee relationship started to shift because employees realized this company could let me go any day even though I have done great work and I have been loyal and I have been here forever. If times get tough, or if they decide to make a strategic restructuring move, then I’m out,” Silletto says.

Because of this shift, employees began giving their children new advice: Never depend on an employer. Since the bottom line always won out, employees could no longer trust that employers had their best interest at heart.

“That’s what my mom told me,” Silletto says. “She was laid off three times as a corporate accountant before I graduated high school. She told me not to trust employers and to never feel obligated to stay with an employer if I wasn’t happy.”

We saw this play out again in early 2020 when the COVID-19 pandemic hit and many companies had to make the difficult decision to lay off workers. “That affects loyalty in both directions long term,” Silleto explains.

Today’s younger employees grew up with a new perspective of the employer/employee relationship: it must be mutually beneficial. Companies only keep staff who deliver value and employees will only stay if the company is a good fit. When either side of that relationship falters, the relationship will end.

Frustration Leads to Job Hopping

With this new contract in place, millennials have been dubbed the “job-hopping generation” as they are most likely to be less engaged at work and open to new employment opportunities.1 Silletto says this is the result of younger employees becoming frustrated at work.

“They feel that no one is listening to them. They feel like seniority wins even though things have evolved over time,” she says. “They are frustrated that the leaders who’ve been in the business a long time are set in their ways, so they don’t see the new business opportunities available today that their competitors are coming to the market with.”

In defense of employers, Silletto points out that younger workers come to the table with less business acumen, so they often do not understand the bigger picture or realize the impact of making one change, such as using a new software.

What’s an Employer to Do?

“We need to come together for those conversations,” Silletto says, pointing out that decisions shouldn’t be made by senior leadership alone or by somebody with a new shiny idea. “Listen to your workers — not just about new ideas and technology — but about what keeps them up at night and what frustrates them in general. Is it a lack of appreciation? Is it a lack of communication across the company or from their manager? Is it a lack of belonging?”

Employers should know if their staff feels like they come to the office every day to do their jobs but don’t really know their teammate or feel like they are a part of the team. Silletto says listening comes with many benefits that can mitigate most employee frustrations.

Ultimately, Silletto suggests that employers must change the model. She points to law firms as an example. Some firms have begun re-evaluating the partner model and figuring out how to become more egalitarian. Moves like this recognize and reward each staff member for bringing value in their own way instead of clinging to a top-down value approach.

“I encourage all industries to re-evaluate the model,” Silletto says. “Companies are coming into the field to disrupt the way it’s always been done and try to think bigger using AI, blockchain and new technologies. How are those going to help our industry? How are they going to advance our industry?”

Silletto also recommends industry veterans take a hard look at their ability to be a leader when it comes to managing today’s new workforce. “Train managers and supervisors and train them better. Get them training that works and changes attitudes and behaviors to make it a better place to work,” she says. “Create better leaders across the organization at every level.”

Disruption as a Path to Success

When companies change their models, the entire framework of an organization can shift. Whether your staff views this change as exciting or encroaching probably has a lot to do with their upbringing.

“I find that most younger workers think disruption is a positive thing, while their parents see it as a negative concept. Because the boomers and Gen Xers were told as children, ‘Do not disrupt your classroom. Do not disrupt the church service. Do not be a disruption.’ It had a very negative connotation when those workers were young children,” Silletto says.

Meanwhile, many millennials look to Mark Zuckerberg as a role model for creating a whole new universe of social media and disrupting the world with Facebook. Silletto says millennials see Zuckerberg and think, “’Wow, he’s a 36-year-old billionaire wearing a hoodie.’ He doesn’t look like the success model from the past.”

While older people look up to successful people who took decades to ascend the ranks, young people are inspired by entrepreneurs who started unicorn businesses. They are proof that you don’t have to wait 20 years to be successful if you disrupt an industry.

Silletto is a frequent speaker at conferences and corporate meetings, virtually now, of course. At one event, she asked a group, “Which staff are you losing and finding hard to replace? Which staff are you struggling to retain and attract?”

For older professionals, the answer was clear: salespeople. They mentioned the difficulty involved in finding and keeping good salespeople and pointed out that it takes years to build relationships in an industry.

Silletto asked a man in his 30s if he faced the same struggle. “He said, ‘No. I don’t have any salespeople,’” she says. “Everyone’s jaw hit the floor.”

Instead of hiring a sales team, this young leader invested in search engine optimization and trained customer service reps who handle inbound calls to upsell and close the deal on the phone. Instead of building long-term relationships with clients, he built a system and a platform where customers go to get the solution. In turn, he was stealing market share from companies that have been around for decades with boots-on-the-ground salespeople.

Disrupting from the Inside

This path is all well and good if you are creating a new company, but what about companies that have been in business for years? How can younger employees bring fresh eyes to an older organization?

“First things first, the younger workers have to see the bigger picture of how the company operates today and what the industry expects, needs and is used to,” Silletto says. “Then they can bring that fresh perspective. They can bring their knowledge of new technologies and tie that idea or knowledge in with the needs of the profession. They must be able to tie the potential solution or disruption to the problem it would solve.”

Silletto says generational training across all staff, and particularly management, is critical today to bridge these gaps. “You don’t want to offer generational training that is based on statistics and based on a book or a report. You really want to have the generational discussion around how were people raised differently and what did that do to their mindset,” she says. “Divorce and layoffs and drive-throughs impacted the mindset of today’s younger workers. This is where that lack of loyalty or sense of entitlement comes in. If you want to know why younger workers are more entitled, it’s because we have drive-throughs. We have Prime shipping that brings things to our houses. We have on-demand television.”

Younger workers also must understand the backstory of their older colleagues. “Baby boomers only had three TV channels when they were children, and they did not get to pick what they wanted to watch when they wanted to watch it. They had to be patient and tolerant and wait for things. They had to earn money over time if they wanted to save up and buy something,” she says. “Younger workers have a credit card and say, ‘I’ll just buy it now and pay it off later.’”

Ultimately, Silletto says we should all come at the generational conversation by asking the questions, “How were you raised? What world did you live in as a child that created your perspective and your lens?”

“You’re much more likely to understand one another,” she says. “And that builds stronger relationships.” •

  1. Adkins, Amy. “Millennials: The Job-Hopping Generation.” Gallup Business Journal.

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