Confessions   //   October 23, 2023

‘I find myself being their IT support’: Confessions of a team leader on the pressures of managing older workers

The workforce is ageing, and it’s raising new challenges. How do you work seamlessly with someone when there is a 30-year age gap while also steering clear of ageism? 

Baby boomers – folks currently aged between 57 and 75 years old – are staying in the workforce for longer than people ever have before. So the gap between the ages of more seasoned workers, as well as those at the start of their careers will only widen further.

While multigenerational workforces are a must-have and an asset for any organization, at times, presumptions and miscommunications can lead to awkward moments. That goes doubly if you’re a young boss.

For the latest installment of our Confessions series, where we trade anonymity for candor, we spoke to a 33-year-old communications executive who manages someone in their mid-60s about the challenges they’re working on overcoming together.  

This conversation has been edited and condensed for clarity.

What is it like working with someone in their mid-60s?

Largely the average age group [at the company] is in their 30s. We’ve got some people who are about 10 years younger, and then we’ve only got a few people who are older. So the older generation is very much the minority within the whole agency, but they have have been here from the very beginning. There’s one person who has been freelancing and came on full time. They’ve been put onto my team and there’s a significant [age] gap between us. It’s the biggest age gap I’ve ever had with someone I’m managing. It’s come with a whole different set of challenges that I’ve just never dealt with or had to think about before.

There’s a common stereotype about the older generation not being able to embrace technology. What has your experience been?

I’m hyperconscious of this because then I overanalyze that I’m being ageist and if I have an unconscious bias that older people don’t know how to use technology. But I do often have difficulty getting them up to speed with the software that we use and I find myself being their IT support a lot of the time. This person goes to great pains sometimes to explain to me that they lived through the age of moving on to email, so it’s not that they don’t know how to deal with new technology. It’s that the technology isn’t working for them. But I can’t help but notice that no one else in the whole team has these technical issues. 

I really struggle with that because I have sympathy for it and I have time for it and I understand how frustrating it is. Something that frustrates me about going hybrid and working from home a lot is that everyone’s had to become IT specialists and that drives me bonkers. So I understand the struggle, but it’s frustrating to always hear that excuse as well as to why they can’t log on or that they’re late. 

I ask him [the 60+ staffer] to share his screen and what to click and how to do it for software issues. But if it’s beyond that, I often pass it off to HR or IT support because it’s just taking up too much of my time. I need to just give the problem to someone who is more familiar with talking through systems and processes because it just takes me a really long time to figure it out. They do a much better job because they’re onboarding people all the time. 

How have you changed your management style?

I’ve just had to become a lot bolder and confident with it. For a long time I was quite apprehensive and nervous to manage him in the way that I manage my other team members where I take the approach of just being super honest and firm, but fair. I was much more gentle because I was nervous about being ageist or saying the wrong thing or seeming patronizing to someone who is older than me. But I’ve come to realize in the last few weeks that actually that’s not fair on my other team members to see that I treat him differently. This person does seem to be performing better with stricter guidelines and they haven’t pushed back saying they know what’s what because they’re older than me. I need to just manage him the way that I would anybody else. That’s fairer than trying to adapt. 

He does make me think about how we work. I see the value in the way that he works, which is technically a bit more old fashioned. But he gets good results often and proves that the way he would go about something is actually the right way. He just can be slow to get tasks done and I questioned if I can say ‘this is taking too long,’ and I really sounded it out. I realized like no, this is just taking too long, it missed the deadline. Of course I can say that.

You’re a millennial, but how do baby boomers and Gen Zers work together?

It hasn’t gone well and I’ve had to deal with that. It’s not that anyone has been rude to each other, but the generation gap was far too much and they couldn’t work together well. It’s more than a 40-year age gap and they could not find their rhythm. It was mutually recognized that they just couldn’t figure it out. With me, it’s more like 30 years and we can figure it out. We moved things around because the 20-somethings and 60-somethings just couldn’t finish the project together.

It was chaos. Different working styles and paces. He needs time to really sit with it and consider the meatier sides of the project, whereas the younger staffer was just like ‘let’s get it done,’ using tools and technology to move faster. They both said they felt like the other wasn’t listening. I do put that down to the age gap more than anything else. They didn’t seem to be able to just joke around with each other and have fun because ultimately they aren’t on the same page. Their references are too different. I hate sounding so broad strokes and stereotypical, but it did happen. That’s why I struggle with this topic.