How to successfully lead a multi-generational workforce

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About 18 months ago, I was actively looking for a new role. I’d been running my own startup for a long time, but it was time for me to get back into the corporate world. 

I had seen a role that looked interesting and seemed to tick all the boxes and I was excited to be speaking to the recruiter. 

He asked me a few questions and then looked me in the eye … well as close to ‘in the eye’ as possible since we were on a Zoom call and said, “I just don’t think I’m going to be able to put your forward.” 

I didn’t say a word. I waited, and when the silence got really awkward, he continued, “It’s just that they’re a really young team and I’d feel weird putting forward a guy in his early 50’s”. 

“I’m 49”, I replied. “And I’ve spent the last 10 years building a global business where over 90% of my team was under 30”. 

“It’s just …”, he continued again … 

To this day I will never know what his follow-up excuse was going to be, but I did know that the best thing for me to do at that moment was to end the call.  

Ageism. Discrimination. Stereotyping. It was a minefield in the making. 

How could he not have realised that today leaders are responsible for employees from potentially four different generations in the workplace – each with its own set of values, attitudes and outlook on life, but when managed well, and encouraged to collaborate can help an organisation to thrive. 

Intergenerational collaboration is very powerful (and important) to the success of any organisation. 

From experience, I can certainly attest to the fact that there can be magic in the generational mix. The conservative Boomer; the independent but collaborative Gen X focused on work-life balance; the Millennial (Gen Y) who is easily bored and typically more challenging of authority; and the self-directed Gen Z not exactly known for being overly team oriented.  

I can vividly recall attending a conference in Hong Kong in late 2006 where the speaker (a human capital leader from a global professional services firm) stood in front of a slide that said by 2025, 75% of the workforce will be comprised of millennials. 

At the time it felt like decades away (because it was!), but 2025 is now just three years away and failure to consider these generational differences could pose a serious threat to a leader’s ability to build a thriving team.  

It’s not always easy and anyone leading a multigenerational workforce needs to have a carefully thought-out strategy to make it work.

Creating an inclusive, collaborative culture and focusing your efforts on improving every employee’s experience is key.

But how do you keep all your team motivated? How do you get everyone on the same page working collaboratively? How do you shift your leadership style to adapt to these different personality types?  

Learning to empower a multi-generational workforce is a very common leadership development trait – one that will become even more important as organisations adapt to employees from different generations adjusting to new hybrid and remote environments. 

So how can you successfully lead a multi-generational workforce? 

Start by encouraging collaboration. You will start to see a more transparent, productive and more engaged team.

Why? Because collaboration will help break down any silos that may have (even unknowingly) developed in the workplace and will also naturally reduce feelings of isolation and loneliness, particularly prominent in more recently formed multi-generational teams.  

Don’t assume your more mature team members won’t want to get involved in agile projects, or that they might not be proficient in some of the latest tools and software.

Don’t underestimate the contribution someone with 25+ years corporate experience can bring into a startup environment.

At the same time, if you are leading a more established or conservative business, don’t accuse a millennial team member of slacking off because they’re constantly on their phone. They’re probably being incredibly productive with all their tools and desktop apps installed on their smartphone. 

Avoid assumptions and generalisations; don’t separate your Gen X employees from your Gen Zs. Instead, make the most of the skills, qualities, and attributes each different age group can bring into your workplace. Acknowledge the differences and embrace them for the overall benefit of the organisation.

Remember that some of the best teamwork happens when assumptions and egos are put aside, and we take on board our colleagues’ ideas, experiences, and commitment for working towards a common goal. 

When it comes to your communication and leadership style, ask your people how they would prefer to be led and communicated with. Just because there’s the perception that Boomers are more reserved, Gen Xers prefer to be given direction, millennials need a more collaborative approach, and Gen Zs appreciate more regular, in-person interactions, this isn’t always necessarily the case. 

Having a flexible communication and leadership style certainly helps when it comes to multi-generational management.

Get to know your team, what works and what doesn’t, their motivations, their learning styles, and so on. This way, you can adapt your own leadership style to match their needs so you can generate the best results. 

At the same time, it’s important to ensure that your multi-generational team members understand each other’s working and communication styles. You might want to suggest they run sessions together where they can discuss this openly. Or you might prefer to invite all your team to complete a personality profile or work styles questionnaire and then discuss the findings as a group. Once again, from personal experience I can share that not every Gen Y works the same way, and not every Gen X has the same approach to communicating. 

Employees coming from different generations will undoubtedly have different expectations about certain work practices, and as their leader you will need to be prepared for how to best respond to and react to these.

Even simple questions around working hours, dress code, work-life balance, availability, meeting etiquette, etc will need to be clarified so everyone is on the same page. In doing so, this will help you be more connected to and engaged with your multi-generational team and create a climate of trust so that your people can perform at their best both as individuals and as a team. 

When all is said and done, everyone working in your business genuinely wants to work there because of the opportunities the company, the role, and you as their leader can offer them … regardless of what year they happen to have been born in. 

So, avoid creating unnecessary generational barriers. Create a unified team and foster a culture where everyone (including the leadership) respects the diversity of experiences brought to the table. Get the generations together formally, informally, in all-hands meetings, whatever works. Let them talk amongst themselves. Ask Gen Ys and Gen Zs to share their ideas, then run them through the filters honed by the Gen X’s experiences. Do the same in reverse. Let the Gen X’s explain the way they’ve always done things and get them to ask the millennials to challenge them and show them a better way. 

By reinforcing the importance of collaboration between the generations, as a leader you will start to see your team members feel more confident and supported and this is clearly a good thing particularly on the engagement and retention front. 

Give it a go! 


Gen X (1971). 

Remember hellomonday provides coaching and support to leaders from every generation, prioritising development initiatives that result in long-term sustained learning and change; and reinforcing habits through curated learning and impactful coaching. 

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