The politics of working for a younger boss

Beena Nadeem explores how we view working for a boss much younger than us.

older worker being instructed by a young boss


As more and more over 50s remain in the workforce and as the tech revolution takes over, it’s likely that, at some point, they will face having to work for a younger boss. This can be a recipe for resentment and frustration.

While we’re told to welcome the world of multigenerational working and the benefits of reverse mentoring, youth boards and increasing diversity, how do we really respond to being managed when the person at the helm is potentially half our age?

For Jules, a writer in her 50s, having a 29-year-old colleague fast-tracked into the post of director at a significant cultural body led to career ruin. The academic institution was largely populated by long-serving experts in their 50s and 60s.

“It was an attempt to redress a balance, to shift the perception of the organisation as somewhat fusty and out-of-date,” says Jules. But while impressive enough on the surface, she said the new director lacked basic diplomacy, social skills and the people-management experience to make people feel valued.

“The young boss’ immaturity, fragility and latent imposter syndrome – she must have felt all eyes were on her –  led to bullying behaviour to get what she wanted,”  she says. The situation left Jules having to take long-term leave through depression and stress and ultimately to her leaving her post. “Before her appointment, we were peers in the workplace and friends outside,” she says.

Youth boards

Chris, who once headed up an international global content and media company, says he’s experienced both the positive and negative sides of having a younger boss.  “I had a young boss with no hands-on experience tasking me with trying to harvest customer data to sell in a way which I knew to be in breach of GDPR and also in breach of the terms of services of some of the big social networks,” he says. “He refused to accept my view and I was forced to explore both whistle-blowing and constructive dismissal routes.”

Chris says the advent of youth boards and panels – to represent young people’s views – show a drive to embrace multigenerational workspaces, but cautions that they don’t always work.

“I have recently set one up, and lots of companies from O2 to Soho House have them too: They are there as an acknowledgment that exec’ teams made up of middle-class white people in their late 30s and early 40s, may need to embrace more diversity in their thinking,” he says. In reality, “on paper these boards are venerated and good for PR, in practice I’ve seen some resentment towards them from directors who ‘don’t want to be told their job by a spotty adolescent’. In fact, youth boards tend to be up to age 27.”

On the other hand, Chris is working in a start-up of hybrid industries around property, events and advertising. “This is a very different environment to a big corporate and there is more age diversity and less ageism. As it’s a new venture, we’re more gentle and there’s more respect for people’s expertise,” he says.


For Ashley Write, an experienced secondary school English teacher from Guilford, Surrey, the placement of a new head of year, who is in his 20s, was difficult for other older staff.  “He’s keen but so inexperienced and lacks subtlety,” she says.

Ashley says he was hired because ‘students could connect with someone of his age’. She adds: “Coming armed with extra paperwork and new initiatives for already overburdened staff was not welcomed. When staff complained they were told ‘that’s why I’ve been hired because of ideas like this’.

“Our older head of department trusts us to do our jobs without us being micromanaged. And he isn’t trying to reinvent the wheel as he’s seen lots of initiatives come and go over his career.”


However, for every experience of some younger bosses being a disaster, there are stories about how others create a more invigorating and dynamic workplace.

Comms’ officer Heather often works with bosses who are 20 years her junior. She also volunteers as a press officer for a political party where the key coordinators are in their 20s.

She says: “I admire the millennial generation: they are smart, hard-working and very skilled. I enjoy learning about different cultures and generations. Now I’m nearing 53, I no longer see myself as mistress of the universe. I need to earn a living, but I’m not battling my way to the top so I can play a more supportive role and let others play the game. Hence there are no abnormal working conflicts of a generational sort for me.”

Meanwhile, for 62-year-old Matthew, a website developer and writer,  there is a lot of prejudice about younger bosses. “We need to lose our sense of entitlement as the keepers of the flame,” he says. “I’ve worked with people who are 23 and work quickly. We should be treating them as peers and not as if we’re in an antediluvian relationship where we’re in authority and they don’t know anything.

“We need to realise they’re grown up with Instagram and Facebook and that it’s not like they’re in possession of something masonic. Let’s strip the mystique out of age and enjoy the task of producing a newspaper or website. After all diversity in the workforce around age is as important as gender and BME.”

Mutual respect

Anton Fishman is an organisational consultant and HR and talent advisor to AI firms. He has worked within management consultancy for decades and cautions against attributing bad bosses to age.  “Far too many people leave workplaces because of stress brought on by being inappropriately managed, but the truth is I don’t really think you can attribute age to this,” he says.

Fishman adds that not only are workplace practices like reverse mentoring – where younger workers mentor older workers – becoming more popular and effective in generating mutual respect and understanding, but that we’re seeing more very young bosses coming to the forefront.

“An awful lot of tech start-ups were started by people in their teens and early 20s and the founders are usually the youngest people in the organisation,” he says,

Increasingly, older people might join the firm later on when it has grown a little. “Younger people might be relatively inexperienced, but they do have vision, leadership and energy and thing that are hugely motivating,” says Fishman. “As they mature, they may start putting some sort of formalised management structure in place and by the time they start to get investors, they start to add a bit of grey hair at either advisory board level or director level. We have tens of thousands of businesses like this.”

As for those seemingly just out of nappies who are being fast-tracked into management roles, Fishman says: “It’s not a new issue: Plenty of organisations have been fast-tracking high potential people for decades; it was not uncommon to have twenty-something people managing 40 or 50 something people back in the eighties, it’s just research into this kind of thing wasn’t long-established.”

If it’s done well and the manager in question has been well trained, he says, it shouldn’t be a problem.

Giving up the upward climb

Another thing that has been happening is older people rejecting the traditional hierarchical career ladder approach, giving up the relentless climb to the top in favour of returning to the things they once enjoyed about their job most.

Fishman gives examples of teachers, who become head of departments and consequently, stop teaching. “Maybe they’re increasingly comfortable with letting go of leadership and management responsibilities and returning to the craft; the profession, the thing they were most passionate about with little regret about giving up their responsibilities,” he says.

Overall, Fishman says we’re a bit obsessed about millennials and Generation Z.

“People bring into work their emotional reactions to engaging with different generations: if your mindset is one of ‘how can this young whippersnapper tell me what to do’ there is no doubt there will be a sort of psychological dimension to this,” he states. Those responses, he says, “are quite natural, but just because they are natural, it doesn’t mean they reflect reality.”

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