A few weeks ago, I sat down with Jon Sheppard, founder of J Sheppard Associates, for the first episode of my new podcast Great Talent, Great Business. Jon is a recruiter who has spent decades placing top talent, and he has a unique perspective on how different generations operate in today’s workforce. He calls it generationality – a term that describes the ways in which multiple generations interact in the workplace. 

The conversation was insightful, especially for business owners looking to optimize their teams and work more effectively across generational lines. It also reinforced something we at WorkBetterNow emphasize: the importance of talent alignment. No matter the generation, the key is knowing what drives people and setting clear expectations.  

The following includes some of my biggest takeaways from our conversation that every entrepreneur should consider. 

1. The Multi-Generational Workplace Is Not New – But It’s More Complex Than Ever

Jon pointed out something that many business owners overlook – especially those of us who have been at this for decades. Workforces have always had multiple generations, but what makes today’s workplace different is the stark divide in expectations and working styles. 

The “fault line,” as Jon calls it, lies between the older generation and a half (Boomers and early Gen Xers) and the younger two and a half generations (late Gen Xers, Millennials, and Gen Zers). The younger group has more options, different priorities, and greater autonomy than ever before. And while older business leaders may bristle at this shift, ignoring it is a surefire way to lose great people who could help you scale your business. 

Instead of resisting, smart business owners recognize the opportunity here. The best talent isn’t necessarily the one that works exactly the way you do – it's the one that helps your business grow, even if it means rethinking how you manage and communicate. 

2. Mutual Mystification: The Silent Killer of Workplace Productivity

One of my favorite concepts that came up in our conversation was something I learned years ago from a professor: mutual mystification. Simply put, it means that too many people in business don’t know what’s expected of them – and neither does the person managing them. 

Jon gave a perfect example. An older executive might send an email at 5:30 PM and expect an immediate response. Meanwhile, a younger employee sees the email, mentally logs it for the next morning, and doesn’t think twice. Neither is wrong – but without an explicit expectation in place, frustration builds. 

The fix? Clear communication. Define what’s expected up front. If you want a response acknowledging receipt of an email by the end of the business day, say so. If you expect client emails to be returned within a specific timeframe, set that standard. Assumptions kill productivity. Expectations create alignment. 

3. The Shift in Workplace Priorities for Younger Generations 

These days, you've likely heard complaints like this: “Millennials don’t work hard”... “Gen Z is full of quiet quitters.” Jon sees it differently. 

Yes, work ethic manifests differently today. But the younger generations bring energy, new ways of thinking, and a deep comfort with digital tools that many of us had to learn later in life. The difference is that they prioritize work-life rhythm rather than work-life balance. Their careers don’t define them in the way they did for Boomers and Gen Xers.  

And while that might frustrate older leaders, it’s not inherently bad. It just requires a shift in how we engage them. 

Jon’s advice? Instead of writing off these generations, leverage their strengths. Provide meaningful work, recognize their contributions, and be open to their ideas. They don’t just want a paycheck – they want impact. The more you embrace that, the more engaged they’ll be, and the more they’ll contribute to your business. 

The Bottom Line: Talent Optimization is a Business Advantage 

One of the biggest takeaways from my conversation with Jon was that great businesses don’t just hire anybody – they hire the right people and put them in positions to succeed. 

At WorkBetterNow, we do that by helping small and midsized businesses tap into our pool of outstanding, full-time talent in Latin America who not only bring exceptional skills, but also the work ethic and cultural adaptability that modern businesses need. 

If you’re a business owner trying to navigate generational challenges, streamline communication, and build a more effective team, the key is simple: Hire the right people and set clear expectations. It sounds obvious, but as Jon and I discussed, it’s where so many leaders fall short. 

WorkBetterNow (WBN) provides outstanding remote talent to small and midsize businesses. WBN’s highly skilled and pre-vetted Latin American professionals are hand-matched for each client’s unique needs. Hundreds of growing businesses turn to WBN to unleash their potential through our exceptional talent, ease of hiring, and ongoing support. Request a consult today!