Freedom Over Possessions

Gen Z values different things than Gen Y and other generations. I remember sitting down with several team members and asking what they would do with accelerated earnings. In a competitive sales environment like ours, money is a big motivator, so I expected the usual responses: buying a car, a house, or something they’d always wanted. But they laughed and said, “We don’t care about that stuff. We want our freedom. Those things will only tie us down.”

That moment was a real eye-opener. I was raised with the mindset that if you work hard, you’ll get ahead in life. But for Gen Z, success isn’t measured by material possessions – it’s about autonomy, well-being, and balance. The root of these generational differences is clear: a lack of communication and a failure by companies and leaders to truly understand what drives their teams.

I’ve learned that professional development and career investment often matter more than a salary increase. Giving younger employees autonomy is far more effective than rigid hierarchies that stifle creativity. Ultimately, Gen Z prioritises well-being and personal fulfillment over traditional career milestones – and that’s not wrong, it’s just different.

Mutual Learning Bridges Communication Divides

Encouraging regular conversations in non-formal settings can help bridge generational gaps. One-on-one discussions that aren’t solely focused on work – such as casual check-ins about life, aspirations, or interests – can create stronger connections and mutual understanding. This helps break down stereotypes and fosters a culture of trust. Generations often have different perspectives shaped by their upbringing and experiences. By openly sharing life experiences – both successes and challenges – leaders and team members can build empathy and see the value in each other’s viewpoints. This also helps break down hierarchical barriers, making communication more fluid.

A workplace that embraces humour, camaraderie, and a fun environment can help ease tensions and foster stronger relationships. However, it’s equally important to set clear expectations about when to be serious. Striking this balance ensures that different generations, with varying work styles, can collaborate effectively without misunderstanding each other’s intentions. Different generations have different communication preferences – some may prefer face-to-face discussions, while others lean towards instant messaging or emails. Being flexible in how you communicate and respect these preferences can reduce misunderstandings and improve collaboration.

Mentorship shouldn’t be one-directional. Encouraging younger employees to share insights with older colleagues – whether on technology, social trends, or new work approaches – creates a learning culture where both sides benefit. Likewise, more experienced employees can offer wisdom and guidance, bridging the generational divide. At JacksonGrant we have a great initiative called Lunch and Learn. In Lunch and Learn, team members get 30 minutes to share their expertise in any topic they wish to discuss. For example, we have had Tik Tok for recruitment, Generational Gap Divide discussions to Wine tasting.

Finally, we also promotes a Culture of Psychological Safety. This ensures that all employees feel comfortable expressing their opinions, asking questions, and raising concerns without fear of judgment is key. When people from different generations feel heard and respected, communication becomes more effective, and conflict resolution becomes easier.

Modern Communication Tools Uniting Multi-Generational Teams

Organisations can leverage technology to bridge generational gaps by fostering seamless communication, collaboration, and engagement. At JacksonGrant, we’ve successfully integrated Happily.ai as a core communication tool to enhance workplace culture and connectivity. Happily.ai has been a key part of our communication strategy since 2021. It goes beyond just messaging – it enables us to share coins, praise, and feedback daily, reinforcing a culture of appreciation and continuous engagement.

One of its most impactful features is the continuous pulse check, which provides real-time insights into team sentiment and morale. This ensures that leadership remains connected to employees across all generations, helping us proactively address concerns and foster a supportive work environment.

By embracing technologies like Happily.ai, organisations can move away from rigid, outdated communication structures and create a dynamic, inclusive, feedback-driven culture that resonates with employees of all ages. The key is not just adopting digital tools but embedding them into daily operations in a way that enhances connection rather than creating division.

The Feedback Revolution

As I mentioned in my previous answer, Happily.ai has been a gamechanger. While it’s a platform designed to enhance workplace engagement and communication, it has also become a valuable bridge between generations, helping older managers adapt to modern communication styles favored by Gen Z employees. A key way older employees use Happily.ai is through its daily feedback feature, where they provide instant recognition for jobs well done.

This real-time feedback mechanism encourages a shift from traditional, structured performance reviews to a more fluid and continuous dialogue, aligning with Gen Z’s preference for immediate, ongoing communication. By using the platform consistently, senior employees have become more comfortable with digital-first communication, reducing generational friction and creating a more cohesive team dynamic.

In addition to this, our HR leader, Ohmmar is an inspirational L&D professional and she has developed additional learning plans which include online training. Ohmmar has also been pivotal in bridging the gap between management and younger team members.

Digital Natives vs. Traditional Communicators

The most common communication misunderstandings between Gen Z and older generations arise from fundamentally different approaches to workplace interaction. Gen Z employees, having grown up as digital natives, typically prefer concise, informal communication channels with quick responses and visual elements like emojis. In contrast, older generations often value more structured, formal communication with complete sentences and traditional etiquette. These differences stem from distinct formative experiences with technology, where Gen Z developed communication habits in an era of instant messaging and social media. At the same time, older generations established their professional communication styles in environments that emphasised formality and hierarchy.

Creating Clarity in Multi-Generational Workplaces

Effective conflict resolution across generations requires creating spaces for mutual understanding instead of expecting either group to fully adapt to the other’s preferences. Successful organisations implement communication guidebooks that recognise various styles as equally valid while establishing clear expectations for when specific approaches are most suitable. Cross-generational mentoring programs have proven particularly effective, as they foster structured opportunities for knowledge exchange while building personal relationships that transcend communication differences. The most successful interventions concentrate on helping employees understand the intent behind different communication styles rather than fixating on the methods themselves.

Beyond One-Size-Fits-All

Organisations can leverage technology as a unifying force by implementing platforms that accommodate diverse communication preferences. The most effective digital workplaces offer multiple channels for the same conversation, allowing for real-time video, structured text, and informal chat options while establishing clear guidelines about which medium is appropriate for different types of information. Companies that find success in this area typically avoid forcing all employees into a single communication approach, instead creating digital ecosystems that support both synchronous and asynchronous work, formal and informal exchanges, and varied levels of detail based on the situation and preferences of those involved.

Learning Both Ways

Digital training tools effectively bridging generational divides by typically combining structured learning with experiential components. Platforms like Udemy and LinkedIn Learning offer specialised courses in generational intelligence, while interactive simulation tools enable employees to practice cross-generational communication in low-risk environments. The most impactful approaches incorporate reverse mentoring programs, where younger employees guide older colleagues through digital platforms while gaining insights into institutional knowledge and industry experience. Such programs are particularly effective when they emphasise mutual learning rather than positioning any generation as more or less technologically capable, recognising that each age group contributes valuable perspectives to workplace communication.

From ‘Noted’ to Three Paragraphs

Gen Z thinks speed equals efficiency, while older generations think structure equals professionalism. I’ve seen it firsthand. A Gen Z employee sends me a WhatsApp message: “Noted.” That’s it. No context. No elaboration. Just “Noted.” Meanwhile, a senior leader types out a three-paragraph email outlining expectations, references, and follow-up steps, only for the Gen Z employee to skim through it and reply, “Okay.” Both walk away thinking the other is inefficient.

Now, let’s talk about the root cause.

Older employees like me were trained in environments where authority and structure ruled. Clear, lengthy emails, in-person meetings, and meticulous follow-ups were signs of professionalism. Gen Z? They grew up on instant messaging, emojis, and voice notes. To them, shorter isn’t rude; it’s efficient. Took me a while to unlearn and learn to be hybrid in the ever evolving environment. At CARSOME, I saw these differences play out on the ground in the Philippines.

I had team leaders who wanted detailed weekly reports and 20-minute calls to discuss updates, while my younger team members wanted to send a quick voice note on WhatsApp and move on. It wasn’t about right or wrong – it was about adapting to a world that moves faster than ever. The moment you accept that communication evolves, not declines, you stop wasting time trying to prove your method is superior.

Reverse Mentorship Key to Cross-Generational Understanding

Let’s be clear, you can’t force a Baby Boomer to text like a Gen Z, and you can’t expect a 24-year-old to write emails like a CEO from the 90s. The key here isn’t making one side conform to the other. It’s about setting communication norms that remove ambiguity. Here’s how I fixed this in CARSOME Philippines:

Clear Rules on Communication Channels
WhatsApp – urgent, fast responses
WorkChat – daily operations and project discussions
Email – formal, documented communication

This way, everyone knew where to expect what, and no one had to “guess” the tone of an email or a message. I told my senior leaders: Stop assuming “Noted” means someone doesn’t care. If you need elaboration/context, ask for it. I told my younger employees: Your boss isn’t a mind-reader. If you understand the task, tell them what you’re doing next. If you don’t, ask them. Context, context.

Reverse Mentorship (You Teach Me, I Teach You)
I have open meetings together with my older managers with younger employees so they could learn how each other work (real hard questions to each other, in front of each other). Suddenly, my senior leaders were using digital tools like Google Drive in real time instead of waiting for email attachments (you know when they need to download it and send instead of attaching the link immediately), and my younger employees started drafting more structured reports. You don’t fix the generational gap by debating who’s right. You fix it by aligning expectations and making both sides see value in each other. Consistent one to one helps a lot too.

Satisfying Both Digital Natives and Traditionalists

I have personally experienced seeing an old-school manager stare at a WorkChat/Google notification like its alien technology. In my experience these past 15 years, I have encountered team members that refused to move away from emails and downloading attachments, while some of my younger team wanted to handle everything on WhatsApp/WorkChat. The solution? Hybrid adoption with clear expectations.

One Centralised Work Hub
We moved all essential updates to a single Google Sheet dashboard (coincidentally built by one of my younger team members). No matter the generation, everyone had the same access to information. The young ones loved the real-time updates. Senior leaders liked that it was structured and trackable.

Asynchronous Workflows
Older employees liked structured morning check-ins, while Gen Z wanted flexible responses. We implemented daily standups via WorkChat so updates were there without requiring unnecessary calls (I personally do not like meetings when a call/message/email would suffice).

Office Hours Instead of Endless Emails
Instead of chasing people across five different channels, we set fixed office hours where employees could come in and clarify things in real time, and specifically on certain days. As not to disrupt our daily operations too much. Guess what? Fewer emails. Fewer misunderstandings. More action.

Most companies blame technology for workplace misalignment, but the problem isn’t the tool. It’s the leadership not setting the ground rules. Also, I keep reminding my team that I detest misunderstanding, if you are not clear, and you refused to get clarifications, then you are the problem.

Real Work, Real Results

You ever try to teach someone who’s been doing business for 20 years how to use a new tool? It’s like telling an F1 driver to ride a bicycle. They know how to get the job done their way, and they don’t see the point in changing. At CARSOME, I’ve had experienced managers refuse to use our new tools, saying “the current way is fine.” Meanwhile, our younger employees were automating half their tasks and getting results twice as fast. So, how do you get older employees to adopt digital tools?

Use Real Work, Not Training Sessions
We didn’t force employees to attend tech workshops; we made them use WorkChat for actual sales updates. Instead of a boring tutorial, we made every department track their OKRs on it. One look and you know whether we are making revenues or losing a sale.

Bite-Sized Tutorials
No one wants to sit through an hour-long training on the new dashboard. Instead, we created 15-minute training sessions that employees could attend without disrupting their work. Multiple slots designed for their convenience.

Gamifying Digital Learning
We rewarded employees who actively used the new tools; I personally use public shoutouts. Screaming, “Well done, keep this update coming!” to any of my employees when they do something right on the new dashboard. You’d be surprised how fast people adapt when there’s recognition involved. Even a thumbs up emoji validates them.

Tracking Adoption & Course-Correcting
We didn’t just assume people were using the tools. We tracked engagement and followed up with those who resisted change. The result? More efficiency, fewer outdated work habits, and a team that actually spoke the same digital language (as close as possible).