When the Top Never Moves: How One Generation Is Blocking the Leadership Pipeline - RegInsights

We grew up on a simple career story. Study, get a job, work hard, move up. The people at the top eventually retire, make space, and hand over responsibility. You keep climbing and one day you are the one in charge. Looking towards 2026, that script feels out of date for a lot of people.

Across business, politics and even housing, a powerful generation is not stepping aside in the way younger professionals expected. Baby boomers are staying in work for longer, holding onto senior positions, keeping board seats and delaying retirement. Many also hold on to property and assets that younger generations assumed would rotate more quickly. The result is a career ladder that feels crowded at the top and slow in the middle.

Before going further, it helps to be clear about who we are speaking about. Baby boomers are usually defined as people born between 1946 and 1964. They are mostly in their sixties and seventies now and still hold a lot of senior roles and assets. Between them and the younger generations sits Generation X, born roughly between 1965 and 1980, who are now in their mid-forties to around sixty and often occupy upper middle or senior management. Millennials, sometimes called Generation Y, were born between about 1981 and 1996 and are now in their late twenties to mid forties, which should be prime time for career progression. Gen Z, born from the late 1990s through the early 2010s, is the youngest working generation, with the older part of this group now entering and moving through early career stages. When we talk about blocked pipelines, these are the groups feeling it most strongly.

On the surface, the picture sounds positive. People are healthier for longer. Experience still has real value. It is good that age is not treated as an automatic exit point. The real issue is not that older professionals are still capable. The real issue is what happens to the leadership pipeline when senior people stay put for too long and systems are not designed for shared power.

The generation that is not moving on schedule

The generation that is not moving on schedule

Baby boomers are a big cohort, and they changed almost everything they touched. Now, as many of them move through their sixties and seventies, something interesting is happening. Instead of stepping out of work life, a large number are choosing or needing to stay in.

There are reasons for this. People are living longer, and that shifts how long they feel they need an income. Retirement has become more uncertain and more individual. Formal pensions are less common, markets are volatile, and many people worry that leaving the workforce too early will put them at financial risk later. Work is also tied to identity. For a lot of boomers, their job is not just what they do, it is who they are. Walking away from that can feel like walking into a void.

If this was just a personal choice, it would be simple. In reality, it shapes entire organisations. When senior figures stay in place longer, the roles beneath them do not open up. The effect is subtle at first. A promotion takes a little longer than expected. A head of department delays retirement. A long serving executive asks to extend their contract for one more year. Over time, the whole structure hardens.

How a stuck top blocks the leadership pipeline

How a stuck top blocks the leadership pipeline

Inside companies, you can feel this in small, everyday ways. High potential employees are told they are next in line, but the line never seems to move. Succession planning looks good on paper but often fails in practice. Development programmes are launched, but the same people keep the final say. Younger managers are given responsibilities without real authority, or temporary acting roles that never become permanent.

Boards often mirror this pattern. They are frequently made up of people from the same age group as the chief executive or founding team and data on CEO and board demographics shows many company heads are now 60 or older. It is natural for them to be sympathetic when a long-standing figure wants to stay on. Pushing for change feels uncomfortable, especially when the organisation appears to be stable. So, the cycle repeats. Senior people remain in place, talking about the future while quietly clinging to the present.

The danger here is not only stagnation. When succession is delayed or mishandled, transitions are more likely to be triggered by crises and handled through disruptive interim appointments. A health scare, a scandal or a sudden resignation forces rushed decisions. Companies scramble to put interim people into roles. Knowledge transfer is incomplete. Instead of a carefully planned passing of the baton, you get a scramble.

From a leadership pipeline perspective, this is the worst of both worlds. Younger professionals have been kept waiting, and when the opportunity finally appears, it arrives in a crisis rather than a structured handover.

The career impact for millennials and Gen Z

The career impact for millennials and Gen Z

For millennials and Gen Z, this power dynamic is not theoretical. It shows up directly in careers and personal finances, with many younger workers reporting anxiety about jobs, savings and the future especially as 2026 approaches and many people take stock of where they are.

Professionals in their thirties and forties often find themselves in prolonged mid level roles. They carry heavy responsibility, manage teams and deliver results, but their title and pay do not reflect the stretch. They are told to be patient, to keep proving themselves, to wait for timing to be right. When they look up, they see the same faces in the same seats they saw five or ten years ago.

At the same time, the classic markers of adulthood are under pressure. Housing markets are tight. Older owners hold onto homes longer, or buy laterally rather than downsizing, which leaves fewer options at the entry level. Younger buyers face higher prices, tighter lending criteria and more fragile employment, and many say they cannot buy a home or retire without an inheritance. The old story about getting a home, building equity and progressing neatly through life stages feels increasingly distant.

Emotionally, this can be draining. It is easy to internalise the sense of being behind. If you are renting, still in a mid level position, and still trying to build savings while prices climb, you might quietly assume you failed at some invisible test. In reality, a lot of what you are up against has very little to do with effort or talent. It is structural.

Frustration is valid, but it is not a plan

Frustration is valid, but it is not a plan

There is a reason jokes and memes about boomers and younger generations land so easily. Younger adults in the US and elsewhere increasingly describe a sense of betrayal and anger over how the economic deal has changed. The frustration is real. Many people look at the opportunities that existed thirty or forty years ago, compare them to their own starting point, and feel short changed.

The risk is getting stuck there. Blaming another generation might feel satisfying in the moment, but it does not move your career forward. Demographics are not going to flip overnight. Many older professionals genuinely cannot afford to stop working yet. Others honestly do not realise how much space they are taking up.

Younger professionals need space to vent, but they also need strategies that reflect the reality of the future, not the fantasy of the past.

Building a career when progression is slower

If the top of the organisation is not shifting, a straight upward climb is unlikely to be your only path. The people who seem to keep moving in this environment often think differently about growth.

One shift is to see your career less as a single ladder and more as a portfolio. Your portfolio can include your current role, projects you initiate inside the company, side work, study, and ventures that stretch your skills. You may not be able to change your title immediately, but you can expand your capability and influence.

Within your current organisation, it is worth getting very specific. Rather than accepting vague promises about the future, ask for clear expectations. What would a promotion actually require in terms of results, responsibilities and timeline. Which skills or experiences are non-negotiable for the next step. Who can sponsor you, not only mentor you. Sponsorship is different to encouragement. It involves someone with power actively opening doors, not just giving advice.

You might also need to be more open to lateral moves than previous generations were. Moving into a new function, geography or business unit can unlock future roles that are not visible from your current spot. Sometimes the quickest way around a bottleneck is sideways.

There will be cases where the honest answer is that your organisation simply does not have the space you need. If you are hitting a hard ceiling with no realistic movement in sight, taking your skills somewhere else is not a failure. It can be a strategic decision to put yourself in a healthier pipeline.

What senior people should be thinking about in 2026

What senior people should be thinking about in 2026

While younger professionals adapt, the responsibility cannot sit only with them. The people currently in charge have choices to make too, especially now, at the edge of a new year.

If you occupy a senior role, part of your job in 2026 is to think seriously about continuity. That means more than identifying a name on a slide. It involves giving potential successors real exposure to decision making, not just implementation. It means stepping back often enough for them to step forward in visible ways.

Boards and owners should review how long key roles are held and whether the composition of their decision making forums reflects the future they say they want, a concern echoed in recent research on CEO and board succession practices. Bringing in younger voices is not about tokenism. It is about making sure the organisation can see around corners, respond to new realities and remain credible to the people it hopes to serve.

There is also a personal element. If your entire sense of worth is tied to your title, you will hold onto it for as long as possible. Developing interests, relationships and a sense of purpose outside formal power makes it easier to loosen your grip when the time comes.

Sharing the future instead of hoarding it

Sharing the future

Generational tension is not new. Older people have always complained about the young, and younger people have always rolled their eyes at the old. What is different now is how visible the gap is and how long it can last when one generation stays in control for decades.

As we’re about to enter the new year, the question is not whether baby boomers are good or bad, or whether millennials and Gen Z are patient enough. The real question is how we design careers, companies and public institutions so that power can move without everything falling apart.

For those who feel blocked, the task is to see reality clearly without letting it crush your ambition. There are still ways to grow, build influence, and shape your path, even if the classic fast track is crowded. For those at the top, the task is to recognise that your real legacy is not how long you stayed, but how well the people after you can thrive.

When the top never moves, frustration builds, innovation slows and talent quietly leaves. When opportunity is shared more deliberately, every generation has room to contribute. In a year like 2026, with so much uncertainty and change already on the table, we cannot afford to waste that potential.

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Dip Media Practices Content Writer | Regenesys Business School Neo is a Content Writer at Regenesys Education with a passion for crafting engaging, purpose-driven content. She contributes to various Regenesys platforms, including the RegInsights blog and Regenesys Business World Magazine, focusing on leadership, education, and personal development. With a background in marketing communications, Neo brings creativity, strategy, and a strong sense of purpose to her work. Outside of the office, she’s committed to using her voice to advocate for education, wellness, and opportunities for neurodivergent individuals.

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