Leading Across Generations: Stuck in the Middle?

The UK real estate industry remains proudly relationship-driven and, in many firms, relatively traditional in structure. At the same time, meaningful progress is being made around diversity, inclusion and new ways of working. And as a result, many businesses now have four generations working side by side.

• Baby Boomers (born approx. 1946–1964)
• Generation X (born approx. 1965–1980)
• Millennials (born approx. 1981–1996)
• Generation Z (born approx. 1997-2013)

In many firms, Boomers and Gen X still hold senior leadership and commercial authority. Millennials and Gen Z are shaping the future workforce. And in the middle sit the emerging leaders. We often refer to these emerging leaders as doer-leaders because they are at peak performance in their day job, but also have people leadership responsibility. They’re expected to deliver performance upwards, whilst leading and motivating downwards.

Through coaching senior leaders, doer-leaders and early-career professionals, we see all angles. And whilst generational differences are sometimes exaggerated, the pressures on those “in the middle” are very real.

It’s easy to stereotype generational differences. But we see tensions falling into a few consistent areas.

Attitudes to Authority

Boomers and much of Gen X often grew up professionally in clear hierarchies. Progression was earned through a somewhat linear progression, and sometimes by time served. Respect for seniority tended to be more important that voicing opinion.

Millennials and Gen Z are more likely to expect a dialogue, access to decision-makers, and an early voice in their careers. They are less likely to assume that seniors in hierarchy are doing the right thing.

This article doesn’t debate any right or wrong, but rather it points out that these differences reflect different social and educational contexts, and we need to take them into account to successfully accommodate multi-generational working.

Communication Preferences

Younger professionals often favour asynchronous communication, for example messaging platforms and structured updates where information comes to them. Many Gen X leaders still instinctively suggest information can sought, for example if you want to find out, “just ask” or even better “just pick up the phone”.

Communication can sometimes be a generational battleground with frequent phrases like these being launched at one another:

• “Why didn’t they just ask/call me?”
• “Why does everything need to be a meeting?”
• “Why don’t they tell us anything?”
• “Why don’t they care enough to...?”
• “Why do they expect it to be so easy?”

Career Expectations Differ

Boomers and Gen X often equate loyalty with longevity, highly respect “go-getters” and “grafters” and believe in a high level of self-drive to make things happen: Career progression should be a reward for these traits.

Millennials and Gen Z are more likely to expect visible progression before they commit; seek meaning and flexibility in their work; prioritise career development speed and / or consider portfolio careers.

This doesn’t automatically mean younger generations don’t want to work hard (as is often the accusation). It means they define return on effort differently.

The Middle: Emerging Leader’s Dilemma

Emerging leaders often comprise Gen X and Millennials who are doer-leaders, and find themselves:

• Being judged upwards on more traditional and commercial metrics e.g. fee income / profitability alone.
• Leading teams who question traditional working norms.
• Trying to protect performance while creating or maintaining engagement levels.
• Translating expectations in both directions.

This complexity is summed up well in the words of a recent coachee: “I’m being asked by my seniors to increase revenue per head and improve standards. At the same time, two of my strongest associates are asking for hybrid flexibility, more feedback and faster promotion. If I push too much, I lose them. If I accommodate, is this weak and setting the wrong benchmark?”

Navigating Generational Differences

We have written before about the business case for curiosity, and it crops up here again. One of the best ways of navigating generational dynamics is to exercise curiosity before making snap judgements.

Our November ‘25 article focussed on how asking better questions increases performance. The same principle applies here. Instead of casting assumptions such as “they’re entitled” or “they’re resistant” ask instead “what’s driving that expectation?” or “what’s the ‘why’ behind this?”. 

When a younger professional asks for flexibility, the “why” may be productivity or wellbeing. When a senior leader insists on responsiveness, the “why” is often client protection and reputation. Understanding the why allows you to separate principles from preferences. Client service standards is often a principle. Whether that service is delivered by phone or Teams is often a preference.

Helpful Practice to Navigate Differences

Make Expectations Explicit: Different generations assume different norms, so be really clear in communication to reduce avoidable resentment, for example with:

• Response times.
• Decision-making processes.
• Feedback methods and frequency.
• Behavioural standards.

Separate Commercial Standards from Cultural Style: Be firm on client integrity; delivery quality and commercial accountability, but offer some flexibility on format; communication style or where risk is low. Being rigid on everything creates unnecessary conflict.

Use Different Language Upwards and Downwards: Be skilled in communicating in both directions. For upwards, frame team concerns in commercial language for example “retention risk increases if development pathways aren’t visible.” For downwards, explain the commercial context for example “our responsiveness is non-negotiable because our reputation drives our pipeline.”

Reflect on Your Own Bias: As well as using curiosity to avoid generational stereotyping, ask yourself “am I reacting to genuine risk, or to preference?” to reduce friction where possible.

Remember

Intergenerational workplaces are here to stay. And there are lots of benefits from accessing both experience and fresh thinking. To maximise these benefits, it’s necessary not to choose sides but to work together. Emerging leaders may see this as yet another challenge, but they are also perfectly placed bring generations together and use this as an opportunity to demonstrate their capability. With just a few adjustments (fewer assumptions, more curiosity and some language changes) significant performance uplift overall can be achieved.  

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