Disclaimer: This write-up is just an opinion piece forged from my own experiences, aimed at fellow Gen Y / Millennials. I do not pretend to be an expert in demographic studies or a business guru (yet) – Iskandar Kavanagh, Product Manager at CTOS Data Systems.


Many business brainstorming events that I have attended, such as workshops, seminars or recruitment drives, as well as in publications and articles that I have chanced across online share a familiar echo – how to deal with Generation Y, a.k.a. Millennials.

It’s odd to think about it really – that the older generations, Generation X and Baby Boomers, are trying to get in my head. To figure me out. To know what makes me tick, even when I am still trying to figure that out for myself. They once labeled my generation entering the workforce as a “phenomenon”, and now call it “a reality we have to face” as Millennials now make up the majority of the working population.


We have to give credit to all the anthropologists, demographers and business gurus working on this. They have made incredible progress solving the Rubik’s cube that is the ‘Gen Y psyche’. Through their findings, they’ve generalised our attributes, mapped out our desires to gain from life, even developed techniques to effectively market products to us, and of course most importantly, integrate us into the workforce as well as bring out the best in us to maximize productivity. Basically, they really know how to manage us.

It’s flattering to be the subject of such buzz, but I recognize that there’s a flip side to this story. The older generations have handbooks on managing us, but I have not chanced across many specific guides for ‘Millennials managing Gen X and Baby Boomers’ until a quick Google search was made as I was writing this article. I found this gem by Association CareerHQ (please feel free to correct me in the comments, preferably with the relevant links. This is just an opinion write-up after all, and I welcome the opportunity to learn).

There are the general articles about employees managing upwards, but these tend to transcend generations and don’t tap into the key considerations and actions needed specifically by Millennials when interacting with the older generations, although this article by Jeff Lail draws parallels from the book, Managing Up by Rosanne Badowski, and applies them to Millennials. For example, he points out that we are afraid of failure. More on that later.

As stated above, this write-up also draws from my personal experiences. I have had the good fortune of often being one of the youngest members of organisations and working teams since starting my career. I have also had the privilege of working with some exceptionally bright people, who have equipped me with a wealth of knowledge and skills to succeed in the workforce. By having worked with a diverse group of people across the three generations I have referred to, I have made some interesting observations as to what has worked best for me when interacting with Gen X and Baby Boomers in the office, whether in the boardroom or by the coffee machine.



1. It is not always what is said, but rather who said it

I’m sure Millennial readers can relate to instances where the key message you’ve been chanting for a few weeks – the one that has fallen on deaf ears time and again – is remarkably well received when stated by someone else. But not just anyone else – often the new Director, the Chairman of the Board, the latest esteemed whitepaper, or the fancy consultant from that highly regarded place. As an ex-management consultant myself, I can verify that some clients are far more receptive to hearing what their own people have to say when it’s passed on from us. Nevertheless, it’s always a surprise when this scenario happens to oneself.

Could it be the data and way it is presented?

No, not when all your training on data analysis and presenting data has been so fruitful in the past.

Could it be that you’re presenting to the wrong person?

No, because you presented to everyone.

Could it be you that’s the issue?

Sadly, maybe.

But not an “issue” in a bad way – just in getting the message effectively across. It’s important not to feel bad about yourself or get hung up about this – you were hired into your organisation because they believe in you and the value you bring. It’s just that sometimes there are so many things going on in keeping the gears of an organisation moving, and moving upwards for that matter, that it seemingly becomes easy for the Gen X or Baby Boomer bosses to downplay what is being said by one of their youngest employees. This could apply just as much to those earmarked as future leaders, especially if that bright young mind has a brilliant new idea every other week. This is similar to a parent appearing desensitized to what their child is saying – often seen in movies where the child points out something incredible happening outside the car window only for the parent to automatically go “That’s nice, dear” without ever realizing the world-changing event that has just occurred meters away.

So how does a Millennial overcome this?

The one formidable solution that has worked for me is to achieve buy-in from one individual that can shift the tide. This needs to be someone with enough clout to influence the rest of the senior management team, yet have enough empathy to take the time to understand where you are coming from. Identifying this individual is up to you. What you need to do then is to have an honest, open conversation with him or her as well as using data to back your message. It may be an idea, a solution, or a warning about a potential roadblock. If your idea or proposal makes sense and benefits the business, all should go well and your identified individual can help champion your message higher up. However, do recognise that this process may take time, which segues into my next point.


2. We need to be patient and understanding

This does not only apply to the Gen X or Baby Boomer boss who needs to empathize and nurture the ‘rebellious Millennials’ now present in their company. Remember, communication goes both ways. Sometimes, the data analysis and presentation training means you follow all the right structures and rules, but are you using the right language?

For example, you need to describe the roles played by:

(1)  your internal tech guy who knows back-end coding, and

(2)  your vendor who is a web developer specialized in developing user interfaces (UI) and mapping the user experience (UX)

As many organisations move from traditional business operations to increasingly digital ones, this scenario may have been played many times over in many different places with many of you readers. Even if you are not from a technical background yourself, it may not have taken you long to learn the tech lingo and understand digital architecture to some workable degree.

However, fellow Millennial, we have to recognize that we grew up with this stuff. We have heard it from our TV shows, documentaries, video games, etc. We have been subconsciously prepared to handle these digital developments from birth whereas the older generations have not had that luxury. So, when describing the situation above, would you use terms like “Java developer”, “UI/UX”, or “API” to your non-tech CXOs without trying to “translate” those terms?

The key here is to put yourself in their shoes and try to be relatable. If your boss is from FMCG (fast moving consumer goods), use terms like “behind the scenes supplier” for the back-end coding and internal tech guy, and “shopfront and cashier” for the UI and web developer vendor. If your boss is a motorhead, use terms like “engine” for IT processors, “bodywork and upholstery” for UI, and “the feel of the drive” for UX. The list of possible similes is endless. Speak their language and it will make the whole communication much more efficient.

Being the expert does not give one the right to be arrogant, but instead to invite others to learn and understand. This does not only apply simply because the Gen X or Baby Boomer bosses stand ahead of you in the hierarchy. It is because this kind of empathy will help in communicating with any down-liners you may have from the previous generations. One day, this will also prove useful when we Gen Y are primarily running the organisations and we have to communicate with Gen Z and whoever comes next.


3. We need to be confident in how we communicate

The time will come when we are the ones responsible for running organisations – for keeping the gears moving, and moving upwards for that matter. There may be very many gears at play too. Some may be known to us, and some may not. That being said, we are being groomed by our bosses, organisations and mentors to fill the positions that they hold and any others that may be invented in future. We need to be ready to fill those shoes.

I bring this up because, although we Millennials may be an entitled bunch, we are terrified of failure. Not of being wrong or corrected, but of trying and failing. This is echoed in the Managing Up article cited above. I have noticed that this has led to some of my Gen Y colleagues shying away from communicating effectively, or at all, with Gen X or Baby Boomer seniors. Instead, they either stay quiet or communicate with an obvious lack of confidence. When one communicates with lack of confidence, in a submissive manner, the busy business manager from a previous generation is far less likely to receive what you are saying, however relevant your message may be. This is probably more prevalent in Asia, where stereotypes of cultures dictate that youngsters should be seen and not heard.

We should learn to embrace our roles in the workforce by striving for the success of our organisations, and whatever challenges that come up along the way. Whether when we are asking a question, pitching an idea, or highlighting a problem; if we are challenged with defining and implementing a solution, we should embrace it. This should be taken as a show of trust and an opportunity to grow as well as to prove our value.

In the end, my three observations are built on the foundation of having an enhanced emotional intelligence, or EQ, and being able to empathise with the audience whom we are communicating with – whether it be Gen X, Baby Boomer, or in the future, Gen Z.


This article was originally written by Iskandar Kavanagh and first published on Linkedin.com, a social network designed specifically for the business community, allowing people to establish and document networks of people they know and trust professionally.



Posted by Iskandar Kavanagh