I was featured in a Dutch national newspaper around 1990. Half a page, no less. The reason? I was a male executive assistant. I also made the cover of the leading management support magazine at the time.

That’s how unusual it was; being a man in this profession warranted media coverage. Three decades later, despite all the workplace transformations we’ve witnessed, men still make up just 3% of the management support profession. This stubborn statistic raises questions that go far beyond simple gender demographics.

When I designed a full-day training programme for Reed Training specifically for male executive assistants, I focused on resilience and managing gender bias. The feedback was striking. Men gathered in that room experienced a rare moment of professional recognition, of not being the oddity, the exception, the one who needed to explain himself.

The unspoken biases

Let’s address what everyone thinks but few say aloud: when a man becomes an executive assistant, people make assumptions. They wonder if he’s gay (and as if that matters). They question whether he lacks ambition (unlike women, who are simply expected to be in support roles). They struggle to place him in their mental model of how organisations should function.

I became the male executive assistant to an executive who had what can only be described as a revolving door of female assistants. They found it challenging to manage his volatile, high-energy style. When I took the role, colleagues made comments like “he needed someone who could stand up to him” or “a man won’t take it personally,” as though emotional resilience were somehow gendered.

The reality was more nuanced. My predecessor had left after three months, describing the role as “impossible.” The one before her lasted six weeks. What these women experienced wasn’t a failure of emotional resilience; it was a workplace that failed to create conditions where they could succeed.

When I survived past the six-month mark, the narrative became that I was somehow specially equipped to handle this difficult executive by being male. This framing does a disservice to everyone: to the women who weren’t properly supported, to me by reducing my professional skills to gender traits and to the organisation by obscuring the real systemic issues at play.

The unacknowledged ceiling

Female EAs often face a glass ceiling. A male executive assistant encounters something different: a presumption that they’re simply passing through.

Early in my career, I was frequently asked: “What do you really want to do?” The question carried an assumption that being a male executive assistant couldn’t possibly be my actual career choice. This reflects a deeper societal bias that views support roles as inherently feminine and therefore less prestigious or desirable for men.

When I revealed that I had deliberately chosen this career path, I often saw confusion or disbelief. People struggled to reconcile my gender with a role they had mentally catalogued as “women’s work,” revealing how deeply gendered our understanding of workplace value remains.

A male executive assistant also experiences a peculiar form of managerial discomfort. Some male executives worry that having a male executive assistant might seem odd to clients or colleagues. This concern reveals more about their insecurities than anything else, but it creates tangible barriers for men entering the profession.

I once overheard a conversation between two senior partners at a professional services firm discussing assistant assignments. When someone suggested assigning the new male executive assistant to one of them, the response was telling: “I don’t want people thinking I can’t handle a female assistant.” The perceived reputational risk of having a male executive assistant was considered greater than the actual professional fit.

The professional gatekeeping

It took me years on probation before International Management Assistants (then still called European Association of Professional Secretaries) accepted me as a full member. I had to prove repeatedly that I was genuinely a senior EA and that this was a deliberate career choice.

Then in 1995 I moved to the UK, where I faced the same battle again. Despite being an international association and me already holding full membership in the Netherlands, I encountered significant resistance. While some of this might have been because I wasn’t yet established as a senior EA in Britain, I couldn’t help noticing how differently the applications of female colleagues were treated. The unstated questions always lingered: Was I serious about this profession? Was this just a stepping stone to something deemed more appropriate for a man?

Professional associations should be safe havens from workplace bias. Instead, they sometimes become its most concentrated expression, with decades of gendered tradition baked into their structures and assumptions.

The double standards

Beyond formal gatekeeping, a male executive assistant often encounters double standards that highlight the gendered expectations embedded in the role.

When a female EA orders lunch for her executive, she’s fulfilling her job requirements. When a male executive assistant does the same, he’s sometimes viewed as being emasculated. When a female EA stays late to finish urgent work, she’s dedicated. When a male executive assistant does the same, colleagues might wonder why he lacks the assertiveness to pursue a “real career.”

I’ve experienced this first-hand. When I would take detailed notes in meetings, executives sometimes seemed uncomfortable in a way they never were with female assistants. There was an unspoken sense that I was somehow diminishing myself by performing tasks coded as feminine.

Conversely, I noticed I was given more latitude to push back on unreasonable requests. Behaviour that might be labelled “difficult” or “uncooperative” in female assistants was often framed as “assertive” or “straightforward” when I exhibited it. This double standard created an uncomfortable advantage that highlighted the gender biases permeating the profession.

The future question

I’ve been wondering lately whether AI’s impact on the management support profession might inadvertently create more space for men. As automated systems increasingly handle the administrative tasks traditionally associated with the role, the EA position is evolving toward strategic partnership, project management and systems thinking.

Will removing tasks historically coded as “women’s work” suddenly make the profession more appealing to men? And what would that reveal about how we value work?

If men do enter the profession in greater numbers once AI transforms the role, we shouldn’t celebrate this as progress. Rather, we should recognise it as evidence of how deeply gender biases have shaped our understanding of work value. The tasks themselves didn’t change in importance, only their cultural coding did.

The path forward

For management support to truly evolve, we need to address these biases head-on. This means:

• Recognising that skills like emotional intelligence, relationship building and communication aren’t gendered traits but professional capabilities.
• Acknowledging the historical undervaluing of administrative work precisely because it was associated with women.
• Creating recruitment practices that don’t perpetuate gender stereotypes about who “fits” support roles.
• Challenging executives who express discomfort with male assistants to examine their own biases.
• When I look back at that newspaper article from 1990, I’m struck by how the novelty of being a male executive assistant hasn’t substantially diminished in three decades. Despite all our progress in workplace equity, this profession remains stubbornly gendered.

Perhaps the real transformation won’t come from technology changing the role, but from finally confronting the gendered assumptions that have shaped it for generations. The future-proof assistant – regardless of gender – will be valued not for conforming to outdated stereotypes but for their ability to navigate complexity, solve problems and create connections across increasingly fragmented organisations.

For the 3% of us who are men in this profession, the challenge isn’t just navigating gender bias. It’s helping to dismantle a system that undervalues support work itself. That’s a transformation that would benefit everyone, regardless of gender.

The question isn’t whether men will enter the profession as it becomes more strategic; it’s whether we can finally recognise that it’s always been strategic, despite being dismissed as “women’s work” for generations.