Crafting Engagement Plans for Multigenerational Teams

𝐒𝐢𝐱 𝐠𝐞𝐧𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐬. 𝐎𝐧𝐞 𝐰𝐨𝐫𝐤𝐟𝐨𝐫𝐜𝐞. 𝐔𝐧𝐢𝐟𝐢𝐞𝐝 𝐧𝐨𝐭 𝐛𝐲 𝐚𝐠𝐞—𝐛𝐮𝐭 𝐛𝐲 𝐩𝐮𝐫𝐩𝐨𝐬𝐞. I believed leadership meant setting direction and ensuring alignment. But over time—I’ve come to see that real leadership isn’t just about strategy. It’s about 𝘤𝘰𝘯𝘯𝘦𝘤𝘵𝘪𝘰𝘯. That truth has never been more relevant than it is today. For the first time in modern history, 𝐬𝐢𝐱 𝐠𝐞𝐧𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐬 𝐜𝐨𝐞𝐱𝐢𝐬𝐭 𝐢𝐧 𝐭𝐡𝐞 𝐰𝐨𝐫𝐤𝐟𝐨𝐫𝐜𝐞. It’s a leadership challenge few of us were trained for. 🔹 𝐒𝐢𝐥𝐞𝐧𝐭 𝐆𝐞𝐧𝐞𝐫𝐚𝐭𝐢𝐨𝐧 (pre-1946): Still serving on boards; shaped by duty and discipline. 🔹 𝐁𝐚𝐛𝐲 𝐁𝐨𝐨𝐦𝐞𝐫𝐬 (1946–1964): ~12% of today’s workforce; value stability, loyalty, and legacy. 🔹 𝐆𝐞𝐧 𝐗 (1965–1980): ~27%; independent, pragmatic, delivery-focused. 🔹 𝐌𝐢𝐥𝐥𝐞𝐧𝐧𝐢𝐚𝐥𝐬 (1981–1996): ~34%; purpose-driven, collaborative, growth-oriented. 🔹 𝐆𝐞𝐧 𝐙 (1997–2012): ~27%; inclusive, tech-native, values transparency. 🔹 𝐆𝐞𝐧 𝐀𝐥𝐩𝐡𝐚 (post-2012): The emerging workforce—digital-first, fast-learning, entrepreneurial. These differences show up in how we work: → Senior leaders value hierarchy; Gen Z favors flat structures. → Boomers seek recognition; Gen X wants autonomy; Millennials want meaning; Gen Z asks, “𝘞𝘩𝘺?” → Gen Alpha? They're learning, building, and questioning earlier than ever. What feels like friction is often just generational dissonance. In a recent HBR piece, put it well: “𝘠𝘰𝘶 𝘤𝘢𝘯’𝘵 𝘪𝘯𝘴𝘱𝘪𝘳𝘦 𝘢 𝘮𝘶𝘭𝘵𝘪𝘨𝘦𝘯𝘦𝘳𝘢𝘵𝘪𝘰𝘯𝘢𝘭 𝘸𝘰𝘳𝘬𝘧𝘰𝘳𝘤𝘦 𝘶𝘯𝘭𝘦𝘴𝘴 𝘺𝘰𝘶 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘪𝘯𝘴𝘱𝘪𝘳𝘦𝘴 𝘵𝘩𝘦𝘮.” That’s the shift we need as leaders: From uniformity → to personalization From authority → to empathy From legacy leadership → to 𝘭𝘪𝘷𝘪𝘯𝘨 leadership I now ask myself not just, “Am I leading well?” but “Am I leading 𝘳𝘦𝘭𝘦𝘷𝘢𝘯𝘵𝘭𝘺?” Because when we adapt our style—not our standards—we help every generation contribute at their best. Great leadership today means adapting with intention and embracing what makes each generation thrive. 𝐏𝐮𝐫𝐩𝐨𝐬𝐞 𝐀𝐥𝐢𝐠𝐧𝐦𝐞𝐧𝐭: Connecting individual roles to a broader organizational mission fosters engagement across all generations. 𝐂𝐮𝐬𝐭𝐨𝐦𝐢𝐳𝐞𝐝 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐜𝐚𝐭𝐢𝐨𝐧: Recognize and adapt to the preferred communication styles of each generation to enhance collaboration. 𝐅𝐥𝐞𝐱𝐢𝐛𝐥𝐞 𝐖𝐨𝐫𝐤 𝐀𝐫𝐫𝐚𝐧𝐠𝐞𝐦𝐞𝐧𝐭𝐬: Offering flexibility can address the diverse needs and expectations of a multigenerational team. 𝐂𝐨𝐧𝐭𝐢𝐧𝐮𝐨𝐮𝐬 𝐋𝐞𝐚𝐫𝐧𝐢𝐧𝐠 𝐎𝐩𝐩𝐨𝐫𝐭𝐮𝐧𝐢𝐭𝐢𝐞𝐬: Promote a culture of lifelong learning to support professional development for all age groups. What shift have you made to better lead across generations? #HarveysLeadershipRhythms #ThoughtsWithHarvey #ExecutiveLeadership #TheLeadershipSignal #GenerationalLeadership #LeadershipReflections #LeadWithIntention #MultigenerationalWorkforce #LeadershipCue #Mentorship

5 Generations. 1 Zoom Call. By 2030, Gen Z will make up around 30% of the global workforce. The same workforce that still includes professionals who sent their first CV by fax. This isn’t a trivia fact. It’s a leadership crisis few are willing to name. I’ve seen this tension play out daily. The problem isn’t age. It’s mindset. And most companies aren’t equipped to deal with it. The data already shows it: teams led by managers more than 12 years older are 1.5× more likely to report low productivity. And yet, the solution isn’t as simple as hiring younger managers. Or introducing another ‘engagement platform’ no one asked for. Every generation demands something different: 1. Gen Z wants asynchronous comms, mission-driven roles, mental health benefits and instant feedback. 2. Millennials want progression, flexibility and trust. 3. Gen X values autonomy and evidence of competence. 4. Boomers expect structure, hierarchy, and consistency. All valid. All incompatible if you're not intentional. So what happens instead? Companies opt for the path of least resistance. They default to legacy systems that please no one. Or they design around one dominant generation, usually whoever holds the power. Bridging the generational divide is less about culture fit and more about infrastructure. You have to: – Build a workplace that supports both structured mentorship and rapid experimentation. – Provide clarity without surveillance. – Design platforms that feel cohesive but flex to different working styles. – Train managers to lead through emotional context, not assumption. And perhaps hardest of all: you have to dismantle the sacred cows of “how things have always been done”. It’s not comfortable. But then again, neither is building a company that lasts.

Leading a Multi-Generational Cybersecurity & IT Team, 25+ Year Perspective. Managing a cybersecurity and IT team with Boomers, Millennials, and Gen Z is like conducting a diverse orchestra. Each generation brings strengths—Boomers’ experience, Millennials’ innovation, Gen Z’s tech fluency—but blending them takes work. **Listen and Adapt** Understand what drives each person. Boomers value process; Gen Z craves flexibility. I’ve seen debates spark over documentation versus quick fixes. Listen to bridge gaps and build trust. Leverage Strengths Pair Boomers’ strategic insight with Gen Z’s knack for new threats. Mixed teams on projects like cloud security blend perspectives. Everyone’s a puzzle piece. Unify Communication Boomers prefer email; Gen Z loves Slack. Set clear norms and train on tools to avoid missteps. Clarity keeps projects on track. Encourage Learning Cyber threats evolve fast. Foster two-way mentorship—veterans share wisdom, younger folks teach tools. A Gen Z intern teaching container security can inspire everyone. Build Unity A shared mission—protecting the organization—bonds the team. Celebrate wins, like stopping a phishing attack, to foster connection. Final Note Embrace differences to create a resilient team. *What’s your trick for multi-generational teams? Share below please.

Worried your hiring strategy isn’t getting the results you want? Here's why: You're too focused on attracting talent Not on retaining and managing them well. Try this instead: ➡️ Tailor your communication style to each generation. ➡️ Align motivation with what drives each group. ➡️ Build a culture that thrives on collaboration between different age groups. From my coaching, years of hiring experience, and research... Here’s what different generations don't like, and what to do about it: Millennials: ➡️ Rigid corporate structures Create a flexible, team-oriented environment. Encourage open communication. ➡️ Lack of transparency Communicate goals, changes, and feedback openly. Keep Millennials informed and engaged. ➡️ No career growth Offer clear pathways for advancement, provide mentorship, training, and development opportunities. ➡️ Outdated technology Invest in modern tools. Streamline processes to maintain efficiency and engagement. Boomers: ➡️ Exclusion from decision-making Involve them in strategic discussions. Support them with tech adoption at their own pace. ➡️ Poor work-life balance Promote a flexible work environment. Respect their boundaries between work and personal life. ➡️ Feeling disregarded Create a culture where contributions from every generation are valued equally. Gen Z: ➡️ Lack of autonomy Give them responsibility. Trust them to manage their tasks while providing guidance. ➡️ Told what to do without context Explain the "why" behind decisions. Encourage independent thinking. ➡️ Hierarchies blocking collaboration Promote flat organisational structures that boost teamwork and communication. ➡️ Inefficient meetings Use digital tools for asynchronous communication. Keep meetings sharp and focused. In other words, create mixed-gen working groups, let Gen Z lead sprints, millennials bridge the gaps, and Boomers advise on strategy. No matter the industry, the lesson remains the same.

In this week’s episode (#56), Leon and I discuss how to harness generational collaboration. We fundamentally believe that despite differences in working styles across generations—Boomers, Millennials, Gen X, and Gen Z—they all ultimately want the same thing: results and impact. The silver bullet is to: (a) harness intergenerational collaboration to pursue shared outcomes, by (b) allowing for diversity in work and communication styles. ⸻ Golden Rules for Collaborating Across Generations 1. Understand where each generation is coming from. Empathy fuels collaboration. Every generation has been shaped by different world events, technologies, and cultural values. Before making assumptions, take time to understand what matters to each group. Boomers may value loyalty and face-to-face communication. Millennials often seek purpose and flexibility. Gen Z thrives on speed and digital fluency. Learn the “why” behind behaviors before judging the “how.” Know and use some of their lingos. For example, the millennials say: - “my bad” instead of “my mistake”, - “ I’m not gonna lie” instead of “to be honest” ⸻ 2. Focus on the Mission—Deliver Results Together Shared goals bridge generational divides. The best way to unify different age groups is to rally around a common purpose. Use a neutral language that is not entrenched in a particular generation eg true north is a fresh new word, whereas KPI is associated with boomers. Set clear true north, KPIs and impactful targets. When the focus is on performance and results, generational labels take a back seat. There is a place for situational leadership which requires ambidexterity ie start the journey with directive style of leadership and shift towards empowerment when the team has developed the competencies to deliver results. ⸻ 3. Build Mixed-Generation Teams with Clear Execution Plans Generational diversity becomes a strength when structured intentionally. Form teams that include members from different age groups and assign roles based on strength, not seniority. Ensure each team has: • A clear True North (shared target) • A 3-Foot Plan (step-by-step actions) • A DMS routine:  – Do it relentlessly  – Monitor continually  – Solve problems recursively This approach fosters accountability, mutual respect, and effective execution. ⸻ 4. Hold Regular Progress Reviews That Blend Styles Establish rhythms that suit everyone. Some prefer face-to-face check-ins; others thrive on digital dashboards or Slack updates. Blend formality with agility. Set monthly or biweekly reviews to align expectations, track results, and adapt plans. Finally, a fundamental characteristic of great leadership is the agility to work across different generations, countries and societies. ⸻ Check it out: https://lnkd.in/dzuEgdDB

Five generations are now present in the workforce, but most leaders only know how to communicate with 1 or 2 of them. Most leaders don’t realize they're missing an essential piece to holistic leadership: Optimization of all age groups. Leading a team requires the skills to manage across multi-generational differences. Here are three critical skills essential for success in this area: 💬Effective Communication Leaders must adapt their communication styles to suit different generations, who may have distinct preferences and expectations for receiving information. For instance, younger employees might prefer quick digital communications, while older employees may value more formal, in-person discussions. Understanding and leveraging these differences promotes clarity, minimizes misunderstandings, and fosters a culture of inclusion. 🔄️Adaptability and Continuous Learning Given the rapid pace of technological and cultural change, leaders must embrace continuous learning to stay relevant and effectively lead a diverse team. This includes being open to new tools and trends while valuing traditional methods where they are effective. Flexibility in processes and policies that cater to varying career stages and work-life needs will also help retain and engage a diverse workforce. 👂Empathy and Emotional Intelligence Leaders must show understanding and respect for the unique perspectives, values, and motivations that each generation brings to the workplace. Empathy helps build trust and enables leaders to manage potential generational conflicts or biases, creating a more collaborative environment. Emotional intelligence also helps understand generational stressors, allowing leaders to tailor support to help employees feel valued and supported at all stages of their careers. By mastering these skills, leaders can create a more cohesive, productive, and engaged multi-generational workforce. For three decades, my work has focused on diversifying workplaces and helping leaders develop the skills they need to create inclusive and equitable spaces. While you don't need to become an expert, it's essential to know how to nurture a culture of transparency and trust in rapidly evolving workplaces. Head to my profile for more information on how to work with me.

How Do I Lead Across Multiple Generations? Most leaders of big businesses are grappling with this very challenge. Leading an intergenerational workforce requires a nuanced approach that values and leverages the diversity of experiences and perspectives across different age groups. 🧑🤝🧑 The key to success is meeting people where they are. This involves: 1️⃣ Understanding Diverse Motivations: Each generation has different drivers. For instance, Baby Boomers may value stability and recognition, while Millennials and Gen Z might prioritize flexibility and meaningful work. 2️⃣ Tailoring Communication Styles: Clear and frequent communication is vital, but the medium matters. Younger employees might prefer digital updates, while older generations might value face-to-face interactions or detailed emails. 3️⃣ Offering Varied Development Opportunities: Different generations may seek different forms of growth. Offering a mix of mentorship programs, online courses, and on-the-job training can cater to everyone's learning preferences. 4️⃣ Creating Inclusive Policies: Flexibility in work arrangements, such as remote work options and flexible hours, can accommodate the diverse life stages and responsibilities of your workforce. Engage your team early and often, ensuring their voices are heard and their contributions are recognized. Avoid the one-size-fits-all approach and instead foster an environment where personalized strategies enhance satisfaction and productivity. Let's lead with empathy, innovation, and inclusivity, creating a workplace where every generation feels valued and empowered. 🌟 How do you tailor your leadership approach to cater to an intergenerational team? Share your insights and experiences below! 👇 #IntergenerationalLeadership #InclusiveWorkplace #EmployeeEngagement #FutureOfWork #Leadership