Managing Gen X and Boomers

Managing Gen X and Boomers. This is what we'll be talking about on today's episode of How to Lead the Podcast for CEOs, founders and leaders who want some clear tools, techniques, and strategies to help them lead well, so their teams thrive and results follow. I'm Kate Waterfall Hill, a leadership coach with real hands-on experience in board level roles for numerous businesses, agencies, and consultancies for over 30 years.

If you like my take on leadership, but would like more support to actually put my ideas into practice, have a look at my website, waterfall hill.co.uk. Many of my clients join me because they need more live, interactive support to help them with their specific roles or organisations. And if you want guidance on your personal leadership challenges, then do head to my website and you can click on a link to ask me a question to make sure that the programmes are good fit for you.

Now, I've covered managing the younger generation in a previous podcast episode, and I thought It was time to turn the tables and talk about how to manage people like me.

And just to be clear, I am Gen X not a boomer,as some people on social media, like to assume that I am just because I've got gray hair. Anyway, today's episode is about managing that other end of the generational spectrum, Gen X and baby boomers. If you've ever inherited a senior team or long serving employee who's been around since dial up internet, you'll know that managing experience can be just as tricky as managing inexperience. These are the people who've lived through recessions, restructures, and more leadership refreshes than they can count. They've seen every fad come and go, and they can spot buzzwords at 50 paces. So how do you lead people who've been leading longer than you've been alive?

We are going to mix things up this time. It's not going to be a word from Linda, but from Alice. Alice works for Linda. Poor old Alice.

“Hey, Jason. You never guess what? This morning Linda got me to help her with her Word document, putting it in a PDF. Again, she says she can't do that sort of thing, thinks it's some sort of weird admin witchcraft. She does the whole, oh, Alice, you are so clever with technology. Can you help me thing? And I fall for every time.

Anyway, she just casually drops into the conversation that when she was younger, she made her own home computer, something about a ZX spectrum. She said she sorted it all herself and everything. I'm stood there thinking, hang on. I wasn't even alive when Dialup was around and she's there making her own computers on her own for fun and then she pretends she can't do anything.

So I said to her, do you know how to do A PDF? She says, of course I do. I just don't want to rather you do it. I'll sit here, have my cup of tea. What you do? All the hard work. I thought cheeky cow. And then I thought, well, fair play, good bit of delegation. I suppose her whole, I'm not very technical, act are load rubbish.

It's a ruse. Make me do her work. Respect.”

So it turns out that even Alice can make assumptions about Linda as well as the other way round.

Let's talk about what's really happening when you're managing Gen X and boomers and how to do it well. Now I have to say I don't like sweeping generalisations because everyone is different, but there are trends that we can obviously see in leadership, and that's what I'm talking about here. What sometimes makes managing the older generation a bit tricky. Well, for all their experience, sometimes older team members can be resistant to change. Not because they're awkward, but because they've seen a lot of initiatives start with fireworks and just end up in more paperwork. They've built deep expertise and networks.

They take pride in being dependable, but that pride can sometimes look like defensiveness. When you say, let's do it differently, They sometimes hear everything you've done so far is plain wrong,

And when you ask for transparency or feedback, they might think I've survived fine without you to date. Why now? And here's the nuance. Experience can make people confident but also cautious.

You're not just managing skills, you're managing identity. So here are four big lessons for managing more experienced colleagues. First of all, please do respect their expertise. Don't be intimidated by it though.

One of the quickest ways to lose the room is to treat experience like it's a problem. If you want their buy-in, start with respect. Acknowledge what they've built, what they know, and what's worked before. Then once that foundation's in place, invite them into the change conversation. Given what you've seen work before, how might we do this?

Even better now? You'll get better insights and avoid triggering we tried that in 2004 response. Secondly, clarity beats charisma. Gen X and boomers grew up in a more hierarchical structure. They're used to direction, but they still want clarity and rationale. If you are younger or newer to leadership, don't try to prove yourself by being overly matey or inspirational.

They value competence over charm. Take some time to spell out expectations without being patronising. Follow through on your commitments. Don't waffle. Reliability earns respect faster than energy ever will. Thirdly, don't assume tech equals threat. There's a lazy stereotype that older workers fear technology.

In reality, many are perfectly comfortable. They just resent being patronised. The key is to offer context, not condescension. Explain why a new tool matters, how it helps them succeed, and what supports available. A phrase that works well is - this isn't about replacing your experience, it's about amplifying it.

And then number four, give feedback with care and calibration. If you've ever given a boomer developmental feedback and been met with frosty silence, you are not alone. This generation often equates feedback with failure because that's how it was handled in their early careers. Your job isn't to tiptoe or to avoid giving feedback altogether, but to reframe position feedback as partnership, not judgment.

Try, here's what's working well, here's where we could build on it together. You don't need flattery, just fairness, clarity, and respect. If you want to dive deeper into that, I have an excellent feedback masterclass available on my website.

And why do so many managers tend to get it wrong? Well, most leaders don't deliberately mishandle experienced team members. They just misread the cues. They mistake confidence for arrogance. They interpret questions as pushback, and they confuse stability with stubbornness. But the reality is that most older employees are quietly wondering if they're being left behind.

They want to stay relevant, they want to feel useful. But they don't want to feel managed, so the trick is to engage them as partners in progress, not obstacles to it. So what can you do differently? Here's how to get the best from your experienced team members without walking on eggshells all the time.

Firstly, invite, don't instruct. Instead of we're doing it this way. Now try. I'd value your take on how we can make this work best. Influence works both ways. coach don't correct. So ask questions that draw on their wisdom. What would you do if you were me? What's worked well in the past that we can adapt here? Thirdly, connect experience to impact. Show them how their knowledge shapes decisions, how they might mentor others or drive consistency.

Number four, encourage reverse mentoring. Pair them with younger team members to share and swap skills. It builds mutual respect and keeps both sides learning. And number five, watch your tone.

So I suggest you ditch phrases like, let's embrace change or shall we step up? They can sound a bit patronising. So try something like, we're evolving this process, or let's make sure this still works for where we are going.

What you could do this week? Well, if you manage experienced team members, here are five simple things that you can do straight away. Ask one of them for advice and actually use it. Publicly acknowledge their contribution in a meeting, review a process together and invite their input on improving it.Give specific feedback, both positive and developmental. And ask them what motivates them now, because it might have shifted.

You'll be surprised how energising it can be when long serving employees feel seen, heard, and still essential. So managing Gen X and Boomers isn't about walking on eggshells or deferring to experience or about throwing their expertise out the window because they just don't fit your image of somebody in your team.

It's about respect. Relevance and relationship and really using that experience to the benefit of everybody. You're not there to replace them. You're there to help them keep adding value in a changing world, because great leadership isn't about age, it's about adaptability, empathy, and making sure everyone feels they still have a place in a future you’re building.

As a Gen Xer myself, I can absolutely say that I have more enthusiasm, energy, and drive to work hard than I probably did in my thirties when I had lots of other things to distract me, like children and school runs and all that sort of thing. So I'd really encourage you to be inclusive and diverse in your team by having lots of people from different walks of life, from different backgrounds and also different generations. You can get a great range of ideas from lots of different people with different types of experience.

So that's all for today's episode of How To Lead Until next time, if you want to be less like Linda, keep leading with clarity, care, and curiosity. Do follow for more leadership insights and spare a moment to like leave a review and share with your fellow leaders to help spread the word about the How To Lead Podcast.

If you'd like my personal support, take a look at my website, waterfall hill.co.uk, and I can help you actually put some of these leadership ideas into practice in your world.

The best leaders are clear on the vision, care about their people, and approach interactions with curiosity, not judgment. Until next time, thanks for listening and don't be a Linda.