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Ultimate Playbook For Gen Z & Millennials

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The workplace is evolving—the clash of the generations can, for some, feel like a daily reality TV show. But ask yourself, what if you were able to turn that drama into a power move?

So your boss has a Boomer birthday, and you’re from a younger squad of Gen Z, Millennials, and Gen X (the tough generation). Here’s your no-nonsense, bold guide to managing up and making waves – the right way – seriously, ‘no cap.’

Cracking the Boomer Code

Your boomer boss started their career when phones were attached to walls, inter-office envelopes were a thing, and mail came with stamps.

Boomers joined a company for their career, from day one until retirement, and they could count on a ‘golden handshake’ at the end their 25 years. Understanding this reality can provide you with a serious strategic advantage.

Generally speaking, Boomers like to dispense with small talk, they prefer direct face-to-face communication, spilling the tea is literal and many view emails and instant messages as too impersonal for ‘real’ discussions. The lesson is, don’t drop the serious topic grenade through an online tool—when something comes up, suggest a one-on-one meeting—it’s not old-school; it’s respect-school.

Tech-Savvy Translator

You can navigate apps and new tech with your eyes closed. Your boss? Perhaps not so much. So instead of rolling your eyes or dropping your jaw when they struggle with the latest software update or password change – offer some help. Organize a short informal tutorial – a subtle way to showcase your skills and integrate cutting-edge technology while showing your value. Not only does this streamline your workflow, but it also makes you indispensable.

Leverage Their Experience

Here’s the thing – your Boomer boss has been around the block a few times. Embrace their wisdom. They’ve done things, seen things, and often know how something will end way before you do. They have not only made the mistakes you’re about to make but also scored some ‘legit’ major wins along the way.

Tap into that treasure trove of experience by asking good questions. Hear the stories, learn from the experiences, and hear their careers lessons. Believe it or not, they know more than you. Take the feedback—it’s not personal.

Taking a beat to listen does double duty: you learn something, and they get to share the wisdom with mutual respect through a mentorship lens. This is a gift—accept it, value it, and embrace it.

Respect and Recognition

Recognition goes a long way. With Boomers – they aren’t just there for a paycheque. For many, their career has become their identify – it’s who they are and they want to be valued for their contributions. Be real and generous with your praise – but make sure it’s genuine they can tell when it’s not. Recognition is a powerful and meaningful way to strengthen your relationship with them and improve morale.

Align on Ambitions

It’s likely that your Boomer boss isn’t interested or planning on a job hop. Think in terms of legacy – they’re building something. Engage with them on the long-term projects that will be there after they leave. Core values are key for Boomers – they should be for all of us – so if you’re not just punching the clock take a minute to invest in their legacy.

Innovation Through Integration

You can’t teach an old dog new tricks – well, sort of. Boomers often appear set in their ways – but they can also be your biggest advocates if you approach it correctly. Instead of presenting overhauls – suggest enhancements. If you want to push for more sustainable office practices, link them to cost savings, brand reputation and efficiency – things that resonate with the bottom-line mindset – it’s what they know and it resonates.

Build Bridges, Not Walls

Relationships are king. Bridging generational gaps is both an art and a science. Embrace learning, be open to experience, and mentor up as well as down. Be reciprocal in your approach—it fosters a work environment that is open to experience, builds psychological safety and respect across age groups, while promoting creativity, and innovation.

Now What?

Navigating the generational divide with a Boomer boss doesn’t need to be hard. It’s an opportunity to flex your interpersonal savvy, emotional intelligence, and strategic thinking. By embracing the experience, you can turn barriers into ladders of success that will help pave the way for a career that’s not only successful but also fulfilling and meaningful.

Managing up isn’t about getting ahead – it’s about contributing to a work culture that values diversity, embraces change and rewards mutual respect. So, take the lead; you might find that your Boomer boss is more of an ally than you think.

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