Connecting Workplace Generations Through Technology

Now of Work (NoW) co-founder Rocky Ozaki discusses the importance of technology in the workplace and how to keep different generations engaged.

Technology is a pillar of the modern workplace. Without effective technology, productivity and employee engagement can suffer. However, some employees from past generations may want to understand how technology can help them but lack the means to do so.

Rocky Ozaki, co-founder of Now of Work (NoW), focuses on equipping companies with the necessary tools to connect generations and keep them aligned with modern ways of working.

The Concept Behind “Now of Work” (NoW)

Ozaki explains that if companies are waiting for some “future” to arrive before making changes to attract, engage, and retain talent, they risk becoming obsolete. The term “Now of Work” is meant to invoke urgency. The present is shaped by three key forces:

1. 1.The connected generation
2. 2.Technology
3. 3.The sharing economy

Ozaki notes that generations themselves aren’t fundamentally different; rather, the world around them has changed. Millennials are now the majority of workers, and Gen Z has entered the workforce. Gen Xers, especially the younger ones, often prefer workplaces designed by millennials rather than those maintained by baby boomers. By 2025, the connected generation could make up 75-80% of the workforce. Companies cannot ignore this shift.

Technology is advancing rapidly, making every company a tech company or soon to be one. The sharing economy is not just about goods and services but also about sharing knowledge and skills. These three forces mean the future is now.

Misconceptions About Future-Proofing

Many companies mistakenly view future-proofing as a distant goal, leading them to approach it incrementally. This is a misconception. Baby boomers are often seen as resistant to change, especially regarding trends like open-concept offices, modern work styles, and new technologies. However, Ozaki argues that baby boomers can adapt when given control and shown the value, as seen with their adoption of platforms like Facebook in their personal lives.

In the workplace, nurturing baby boomers and involving them in the process can help them adapt. A human-centric approach to change is key.

Generational Expectations and Approaches

Ozaki emphasizes that we live in a hyper-personalized world. While younger generations are more aware of this, organizations should personalize their approach to different audiences. There is no need for everyone to work and communicate in the same way.

Meeting people where they are is important, but so is exposing them to modern ways of communicating. Reverse mentorship—pairing a younger person with a more experienced one—can help bridge gaps. The younger person can demonstrate the value of new communication tools, fostering empathy and understanding.

Freedom and Choice in the Workplace

Startup culture often emphasizes freedom and choice. Ozaki shares that when companies introduce remote working policies, initial uptake is high, but over time, only about 30% regularly use it. The key insight is that employees value the choice itself, not necessarily remote work. People like collaborating in person but want the option to choose where and when they work. Providing choice increases investment in work. When assigning tasks, asking for volunteers rather than delegating can also increase engagement.

Leadership and Technology Trends

Leadership must understand how exponential technologies will affect their business. Without this understanding, companies risk being disrupted or unable to adopt new technologies quickly enough. Employees want to work with great technology, and lacking it can lead to staff attrition and reduced competitiveness. Employees are aware of industry trends and expect their organizations to keep pace.

Making Past Generations Comfortable in the Modern Workplace

Ozaki suggests that organizations should focus on human-centric approaches, nurture employees through change, and encourage knowledge sharing across generations. Reverse mentorship and personalized communication can help bridge generational gaps and make all employees feel comfortable in a modern, technology-driven workplace.