Holly Hunt, Founder & CEO of Women in Digital, shares her reflections from the Great Generational Debate.

At Women in Digital’s Great Generational Debate, we brought together Team Legacy (Gen X and Boomers) and Team Next Gen (Gen Z and Alpha) to do something the workplace rarely makes space for — genuinely listen to each other. There were no winners. That was never the point. But walking away, I couldn’t shake a sense of unease.

As a Millennial, I found myself caught in the middle — nodding along to both sides. I related to Team Legacy’s belief in rolling up your sleeves and earning your seat at the table. I also respected Team Next Gen’s clarity about their own worth, their appetite for purpose, and their willingness to challenge systems that frankly do need challenging. But there is a tension that the debate surfaced that I don’t think we can afford to gloss over.

The uncomfortable truth about timing

Team Next Gen enters the workforce with higher expectations than any generation before them — and in many ways, rightly so. They want to understand the why behind commercial decisions. They want to be part of strategy conversations early. They will move roles if growth stalls. They have clearly defined boundaries and they are not afraid to use them.

These are not inherently bad qualities. In fact, several are admirable.

The problem is the timing.

AI is not a future threat — it is a present one. The entry-level roles that have traditionally been the training ground for careers in technology are already being replaced. The graduate pathway that Team Legacy walked, and that Millennials like me benefited from, looks fundamentally different today. In that environment, the expectations Team Next Gen are bringing to the table carry real
risk. When a junior employee signals early that they will leave if they aren’t in strategy conversations, or if the why isn’t clearly communicated — the cold, commercial reality is that it diminishes a leader’s incentive to invest in them. Mentorship, sponsorship, and genuine career development require time. And time-poor leaders will direct that investment where they see loyalty and commitment in return. Team Next Gen may be inadvertently doing themselves out of the very careers they want.

What this generation gets right

This is not a dismissal of Team Next Gen — far from it. One of the most memorable moments of the debate was a Next Gen panellist describing life as a game of chess: a game of strategy where you can never focus on just one piece. It was sharp, considered, and insightful.

Team Legacy openly admired their self-awareness and their refusal to derive all sense of worth from a job title. That evolution matters.

And they are right that the systems that got us here are not necessarily the systems that will take us forward.

The bridge worth building

The generational divide in the workplace is not a problem to be solved by one side conceding to the other. But it does require honesty.

For Team Next Gen: there is real value in seasons of intensity — in getting on with the job before you fully understand the strategy behind it, in demonstrating commitment before demanding flexibility. Adapting to the commercial realities of work, particularly in a rapidly shifting labour market, is not selling out. It is survival — and ultimately, it is how you build the influence to change the things that need changing.

For Team Legacy: the low seasons matter too. Supporting interests outside of work, investing in the development of junior talent even when the return is uncertain, and genuinely learning from a generation that has grown up with the world at their fingertips — literally — is not weakness. It is leadership.

As for me — I make no apologies for loving my work. For finding purpose in it. For believing that a career built with commitment and pride is something worth having. And I don’t think
Team Next Gen should apologise for wanting more from life than work alone. But in a world where machines are quietly taking the entry points, this generation cannot afford to let impatience cost them the career they are capable of building.

The robots are not waiting. Neither should they.