Transforming the Workplace: Generational Insights from Jason Dorsey

By 2030, Gen Z will make up nearly a third of the workforce, fundamentally changing how teams communicate and collaborate. Is your organization ready to adapt?

At this year’s Deltek ProjectCon, Jason Dorsey, a leading expert on generational dynamics delivered a keynote packed with actionable insights. His research-backed findings reveal the preferences, values and communication styles of each generation, equipping leaders with tools to foster collaboration and drive innovation. For project-based businesses, Jason's insights offer a roadmap to creating inclusive, high-performing teams.

Strategies for Cross-Generational Success

One of Jason’s key strategies involves creating a 'generational snapshot' of your workforce. This visual representation of generational demographics helps leaders anticipate workforce trends and adapt strategies for communication, recruitment and retention. “By giving leaders numbers and visuals, they’re almost always shocked,” Jason noted. This data-driven approach provides a foundation for aligning workforce strategies with evolving team dynamics.

Jason emphasized that generational insights are not about labeling one group as better or worse but about understanding each group’s unique perspectives. “It’s really about understanding where they are coming from, how they view the world and creating a space for them to be who they are,” he explained. Simple actions, like providing quick feedback or using visual learning methods, can significantly boost engagement across teams.

To bridge generational gaps and foster collaboration, Jason recommends the following:

• Provide Generational Training: Offer training sessions to educate employees and leaders on generational differences, highlighting collaboration techniques.
• Implement Cross-Generational Programs: Design opportunities such as cross-generational mentoring to foster mutual understanding, learning and respect.
• Encourage Story Sharing: Create spaces where employees can share experiences, build deeper connections and learn from each other.

By embracing these approaches, organizations can build a more inclusive, dynamic and collaborative workplace.

Leadership's Role in Fostering Inclusivity

Setting the Tone

Leadership plays a pivotal role in creating a thriving multi-generational workforce. Jason highlighted the importance of 'planting a flag' that values every generation equally and adapting strategies to unlock each generation's potential. “Leadership is the driver of culture within an organization,” he emphasized. Leaders must foster a culture of trust, performance and inclusivity—where every generation feels valued and understood.

Effective leadership requires a commitment to education and strategies that honor the unique contributions of each generation. This doesn’t mean catering to or coddling specific groups; rather, it’s about equipping all employees with the tools and support they need to be successful. Leaders should recognize their team’s diverse communication preferences and work styles of their teams and adapt accordingly.

Authentic Recognition

Jason also stressed the importance of meaningful recognition. “It’s not about giving everyone a trophy,” he explained, “but finding authentic ways to honor each generation’s contributions." Whether it's public acknowledgment, personalized feedback, or growth opportunities, tailored recognition can build a culture of appreciation and respect.

Leaders can create workplaces where diverse perspectives are celebrated by addressing generational challenges head-on and encouraging open dialogue. This approach not only strengthens collaboration but also drives innovation and productivity, making generational diversity a key organizational asset.

Tools & Trends Shaping the Future of Work

Supporting Diverse Technology Preferences

In today’s workplace, technology is key to bridging generational divides. Each generation has unique communication styles and preferences—from email and text messages to video calls. Leaders must assess current tools and ensure they align with these generational preferences. For instance, younger employees may favor quick, informal messaging, while older generations might lean towards more traditional methods.

A one-size-fits-all approach to technology and communications doesn’t work. However, by blending technological flexibility with thoughtful communication strategies, organizations can create an environment where every employee can succeed.

Leveraging AI to Bridge Gaps

Artificial Intelligence (AI) holds considerable potential for enhancing communication, automating routine tasks and freeing employees to focus on high-value work. It can also help tailor communication strategies, ensuring messages are delivered in the most effective way.

AI will also be pivotal in talent development by identifying skill gaps and offering personalized training programs. However, AI’s integration comes with its own set of challenges, including skepticism and mistrust. As Jason noted, “Leaders must demonstrate AI’s positive impact on the workforce, ensuring it enhances—not replaces—human capabilities.”

The Rise of Hybrid and Virtual Work

For leaders, staying ahead of trends means more than just adopting new tools—it requires fostering a culture of continuous learning and adaptation to stay competitive in an increasingly dynamic workplace.

One of the most significant shifts is the rise of hybrid and virtual work, particularly as Gen Z views remote work as a standard expectation. Organizations must embrace this change to attract and retain top talent.

Shorter Generational Spans

As Jason predicts, the pace of technological and societal change may blur traditional generational distinctions. “The traditional concept of generations might even disappear, as the rapid pace of change creates shorter generational spans.”  This shift will require organizations to stay agile and continuously adapt to new trends and technologies.

Redefining User Experience for All

Recognizing these changes, Deltek has prioritized creating personalized and seamless experiences that drive productivity and satisfaction for a multi-generational workforce. Deltek Harmony, our new design experience, simplifies complex functionality into a cohesive and easy to navigate user interface.

Rather than expecting users to adapt, we’ve reimagined the user experience to evolve with their needs. Harmony reflects our commitment to empowering project-based businesses by fostering collaboration and enabling teams to focus on what matters most.

The workplace of tomorrow demands flexibility, inclusivity and innovation. By embracing Jason's generational insights and leveraging tools like Deltek Harmony, your organization can lead the way in building a culture where every generation thrives. To learn more about how Gen Z will change the future of business, check out Jason Dorsey’s latest book The Zconomy.