How to succeed with an older boss

How to succeed with an older boss

    Older employees are staying in the workforce at unprecedented numbers while younger ones are joining faster than ever before.

    Problems can arise when generational differences lead to incompatible work styles and expectations of the workplace and each other.

    With patience and respect for your differences, you and your boss can have a productive working relationship.

    Getting a promotion at work can take time, so those in supervisory positions are often significantly older than those they supervise, frequently by a generation or more. How should a young new employee engage with a boss their parent’s age? This article aims to help new entrants to the workplace navigate these uncertain waters.

    Why are generational differences more extreme than ever before?

    Current economic conditions have led some workers to delay retirement to keep building their savings. Meanwhile, some young workers are joining the workforce before completing school to reduce student loan debt and start earning sooner. A recent study showed that before the loan repayment hiatus, the average student loan debt payment was $300 a month, with $1.75 trillion owed by 46 million borrowers. So, while older workers are staying in the workforce at unprecedented numbers, younger ones are joining sooner than before.

    This has led to an unprecedented range of ages in the workforce. A problem arises when these age differences results in different styles of work and different expectations of the workplace and of each other. Failing to understand these differences can result in miscommunication, ill will, and unnecessary stress. Demystifying potential generational differences can help prevent misunderstandings, not to mention give you a better chance at a good reference when the time comes to take the next step in your career journey.

    How to engage with an older boss

    For simplicity, we’ll use labels to describe the generations currently in the workforce, but no one person completely fits their generational profile, and the generational labels are fluid. In fact, the only generation to have an official government definition is the Baby Boom Generation. Yet, these general categories by age do have some value in understanding the key events of a certain time and how they shape the values and ideas of the individuals who grew up in those times.

    For simplicity, rather than using all the named generations, they are grouped for this article. The ‘older’ generation in the workplace are those born in 1980 and before, and the ‘younger’ are all those born after 1980, also referred to as ‘digital natives’.

    What makes your older boss tick?

    While not everyone born before 1980 feels the same way, there are some helpful points of reference about what they experienced growing up and how that shapes their attitudes today. Boomers and Generation X largely grew up in 2-parent homes where their father was the breadwinner and the mother was a homemaker. Many saw their father stay at the same company for an entire career.

    » Read: Switching careers later in your professional journey

    Why does this matter? Because it shapes what they expect from their jobs. Research shows that Boomers and Generation X expect they’ll be stay at the same job for years or even decades. And many view work as toil, or as ‘punching a clock’, that is, as a means to an end – a way to get a salary that pays for a nice lifestyle, rather than as their purpose or a way to fulfill a passion. While not true of all members of these older generations, it may be true about your boss.

    Research shows that Boomers and Generation X expect they’ll be stay at the same job for years or even decades, And many view work as a means to an end – a way to get a salary that pays for a nice lifestyle.

    Why is your boss that way?

    Perhaps the biggest difference among the generations is the technology changes they lived through. For Boomers, the defining technology advance was the television. In the 1940s, owning a TV was rare, but during the 1950s, TV ownership grew tenfold, from 9% of the population, to 88%.

    • For Generation X, the defining new technology was the personal computer. In 1980, personal computer use in the home was nearly nonexistent, but today has grown to be ubiquitous.
    • For the younger generation, computers have long, if not forever, been part of their lives, along with the Internet and mobile devices.
    • For the older generations, these are new technologies that can be intimidating to use. According to research from the consulting firm McKinsey, as shown in table below, 17% of consumers choose to be offline completely, while another 25% are not comfortable with digital channels and use them only when necessary.
    Digital by lifestyle (23%) For these consumers, digital is fully integrated into their lives. They don’t perceive a separation between the digital and traditional worlds – that is, they use social media every day and tend not to watch traditional TV or read newspapers.
    Digital by choice (35%) Individuals who enjoy the advantages that digital brings, such as Netflix, Skype, YouTube, online check-in for travel, and online banking transactions, have options for how they engage but opt primarily for digital channels.
    Digital by need (25%) Digital is beyond the comfort zone of these consumers, who engage with digital channels only when necessary.
    Offline society (17%) Individuals who live in the nondigital world and prefer personal contacts make up nearly one-fifth of all customers. They use bank branches, shop in brick-and-mortar stores, and typically do not use the Internet.

    What makes young people unique at work?

    While not true of all younger workers, research shows that they are more likely to be motivated to work for a cause they care passionately about, and may prioritize work-life balance over status or salary when choosing a job. The recent ‘great resignation’ of workers included 25 million people who left their jobs in the second half of 2021, and a total of 4.5 million in November alone. This is the highest quit rate since the U.S. government began tracking this trend in 2000. So, employers must do what they can to retain workers, which gives young workers more leverage than ever before.

    What skills do young people have that their bosses don’t?

    Younger workers have always had the Internet as part of their lives, and some have shared details of their personal lives on social media for years. While older generations may have gone to a dictionary or encyclopedia, younger ones immediately seek out information on digital channels, whether on a computer, tablet, or mobile phone.

    » Read: Can micro-credentials enhance your career?

    Older workers are developing digital skills, but unlike younger workers, did not grow up with these technologies. As a result of being digital natives, younger workers may have greater skill than their bosses at setting boundaries around work when working remotely.

    As a result of growing up surrounded by technology, younger workers may have greater skill than their bosses at setting boundaries around work when working remotely.

    Unlike the older generation, many younger workers were raised in 2-career families and watched their parents juggle work and family life. Some saw their parents struggle with job loss in the post-9/11 economic downturn. Many were children or teens during the 9/11 attacks and lived through the post-9/11 wars during their youth. This shaped the perspectives and values of younger workers, who are less likely to want to spend a long time at the same job than their parents.

    Younger workers are ‘adapting quickly to a world undergoing rapid technological change. They’re optimistic, they’re confident and they’re pragmatic at a time when it can be difficult just to get by,’ says TIME writer, Joel Stein. They are also part of the most racially and ethnically diverse generation ever and are highly educated (and many also saddled with student loans). Additionally, they are the largest group in the current workforce.

    Younger workers are part of the most racially and ethnically diverse generation ever and are also highly educated.

    Many younger workers don’t remember when people weren’t reachable when traveling, and as a result don’t understand the idea of sitting at a desk to work. They are asking for flexibility in where and when they work. And, the move to remote work during the pandemic has accelerated the expectation that remote work can remain.

    millennials at work

    What are the keys to working successfully with your boss?

    The keys to success in having a harmonious relationship with a boss who was shaped by such different culture and technology are as follows:

    Be clear about what you need

    Your needs at work may be different from what your boss expects, so it’s helpful to clarify them so there are no misunderstandings or wrong assumptions. First, get clear in your own mind on what your goals are, what you want to learn, how you want to progress in the job, and the help you’ll need from your boss in order to be successful. Write it down so you’re clear in your own mind before explaining it to your boss.

    Have an honest conversation with your boss

    You are probably just as much of a mystery to your boss as they are to you. So, it’s important to have a conversation that is open and honest and to do it in a way that respects your unique perspectives. You’ll need to explain yourself clearly to your boss and don’t assume they understand you immediately. Imagine you’re talking to someone from a foreign country for the first time and are curious about their ideas and values – you and your boss may be a lot like people from different cultures! So, go slowly and check in frequently to make sure you are being understood. Doing this respectfully with your boss can help build open communication channels.

    When you don't know why, ask

    Many older workers are more deferential to authority and will do a task without asking why it’s important or how it contributes to mission. Don’t hesitate to ask your boss why you are being assigned a task, how it fits into the larger picture of what your team or organization is trying to achieve, and if you need to, also ask how your boss can help you if you get stuck along the way. No one wants you spinning your wheels wasting time if you get confused, so speak up.

    Seek input before acting on an idea

    You’ve likely got some great ideas on how to improve the work. A basic tenet of management is that change is always more successful when you get buy-in during rather than after the fact. Whether choosing a movie to watch with a friend or deciding what to cook for dinner with a roommate, many decisions, even when you don’t completely get what you want, feel better in the end when we have input. Remember that your boss may want input on your idea in order to get fully behind it, so check in before charging ahead. As a bonus, you may get some advice from the boss on pitfalls to avoid that they themselves have hit before in their years of experience.

    Request progress updates

    Many workers are used to receiving very little feedback on their work. That’s unfortunate, because feedback helps us learn and improve our skills. So, if you have been working on a project for more than a couple of months, or if you reach a milestone and wonder how you are doing, ask. You may get praise or helpful constructive feedback that can help you achieve your goals sooner. Remember, your boss may not be used to giving feedback, but you deserve it.

    Respect rules, even while changing them

    You may see yourself as one day being in charge of the organization, but you’ll need to take it one step at a time, and you don’t want to burn bridges on your climb to the top. The best way to do this is to abide by the cultural norms of your organization even if you are going to try to change them. For example, you should avoid using the informal tone you might use with friends in conversation or in text or chat messages and avoid all slang terminology when talking to or sending an email to your boss. Partly, this is to show them some respect, but it also helps them have a better understanding of what you’re communicating as they may not understand the jargon or slang that you are using – and no one wants to feel excluded or stupid.

    Be flexible about flexibility

    Many workers, having tasted remote work during the pandemic, are asking for it to continue. Some bosses are resisting, often because of rules set by the organization or by unions that prevent complete flexibility. Your request may need to fit within some parameters that neither you nor your boss can control. Rather than resenting what you can’t control, think of it like the weather, something you can work around and do your best to mitigate the downside of. When approaching your boss about continued remote work or flexible hours, approach with an open mind and keep your boss’ goals in mind too. If you are flexible and handle the conversation as a give and take, you may get more than you expected if not all that you hoped for.

    Communicate strategically

    You’ve probably got a great perspective on how the work could be done more efficiently, especially if you are new and have a fresh set of eyes on old routines. Or, you may have an idea for a community service project that your team can do together to make a difference while getting to know one another better. Or, perhaps you want to initiate a Slack channel for sharing ideas and suggestions, and your boss doesn’t even know what Slack is. Bring your ideas to your boss, but frame it as a helpful suggestion and a way to make progress on common goals, rather than a criticism.

    Younger workers are a tremendous asset to their organizations – a more educated, multicultural, and digital savvy group that has a lot to offer in connecting work to purpose and in driving an ethos of transparency and inclusion which is increasingly demanded in today’s society. With patience and respect for your differences, you and your boss can have a productive working relationship. The key is to not expect them to be like you, or to change to conform to their expectations. Instead, see to understand them, be adaptable (enough), and communicate your perspective clearly.

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