Judgement
- Simon Deen

- Jul 31
- 4 min read
We live in an era where an incredible amount of information is available to a large percentage of the world in a matter of seconds. Where people can, and do, ask their AI assistant of choice anything and everything, and receive an immediate response.
So when PrimeResi asked me to write a piece on what it takes to get deals over the line at the moment, and how we’re holding transactions together in these challenging times, I thought I’d start by asking Claude for his view.
Claude’s advice was to stay in the middle of the legal chain, manage the psychology of both parties, re-qualify buyers at offer stage, keep a warm buyer queue ready in case of any issues, and as an agent, always be the calmest person in the room. And I can’t say that I really disagree with any of those points.
But the one thing Claude misses is that none of those things are possible without something else. Something that’s essential if you want to navigate the often challenging path between agreeing terms and exchanging contracts. It’s something which Claude can tell you about, but can’t actually give you. Experience.
Of course, when you start out as an Estate Agent, or in any industry for that matter, you have no experience. And we’ve already established that even in the AI age, no one, not even a machine, can simply give it to you. But thankfully, there’s a solution. All you have to do is position yourself close to those who have it, and then spend time with them. Preferably 10,000 hours.
When I started my career as an estate agent back in 2003, I knew very little beyond what I’d been taught at home, in classrooms and lecture theatres. But fortunately I was surrounded by people who knew a lot. I learned first from listening and watching, and later, trying to emulate. Over time, I took different methods from different mentors and developed my own style.
Those mentors had a certain confidence. That came not from faking it until they were making it, but having worked through different economic and political cycles. From selling multiple properties per year, over decades. By making mistakes and learning from them.
Across London there are hundreds of agents who learned the skill of estate agency in similar ways. Take John Hunt’s Foxtons. Twenty years after his exit, there’s a large cohort of people working top jobs at industry stalwarts, in addition to some amazing entrepreneurs, who all started their professional life there.
Parts of that 2000s Foxtons culture wouldn’t survive in 2026. But the evidence doesn’t lie, and what those young agents learned has stood them in good stead. Not only in their own careers, but also for the clients they’ve guided through countless difficult transactions.
The estate agency landscape is shifting dramatically, as is the workplace in general. The office junior role, certainly as I knew it, is now redundant. AI will continue to replace entry level roles, and that will save businesses money in the short term.
But at what cost? A whole generation of estate agents either choosing, or being forced to, forgo the invaluable training that I, and many others like me, received?
Whether it’s the structured kind that Foxtons, Knight Frank or Savills gives you, or the unstructured, osmosis based type that I received, it doesn’t matter. What mattered, and still matters, is that young agents were learning. From actual people, in real life.
So what does it take to get deals over the line at the moment? Well, in our experience, it’s the corollary of experience - sound judgement.
When to push, and when to let a situation breathe. When to empathise and re-assure.
Choices that don’t necessarily come from conscious calculations, but instead the ability of an agent to recognise patterns and understand how best to navigate the inevitable challenges as they arise.
Like keeping parties’ interests aligned. Individually, by making them feel heard, seen and understood. And collectively, ensuring that everyone is working towards the same goal. Managing the other professionals in the transaction - the lawyers, the surveyors and the mortgage brokers - so that they’re all pulling in the same direction too.
The skill of judgement has never been more important than it is now. We’re in uncertain times, politically and economically. Expertise in general, even amongst those whose opinions were once seen as authoritative - doctors, lawyers and accountants - is now being challenged.
Amongst buyers, the availability of data means that they have access to the same information that was once the preserve of agents. We’re dealing with savvy buyers armed with reams of information, ChatGPT’s interpretation of it, and an accompanying spreadsheet.
But buying homes should never be just about data.
It should be about the last twenty years of one family’s life, and the next twenty years of another’s. It should be about hopes and dreams. About things that can’t always be rationalised.
Lower barriers to entry into estate agency and an increased number of agents operating in every area is creating a paradox of choice for sellers, with more options not always leading to an easier decision making process.
Homeowners don’t just want more choice, but more confidence in the choices presented to them.
Buyers don’t just want more facts, but to have their views either confirmed or challenged by people with long track records, who know exactly what they’re talking about.
Whilst every situation is different, nearly all are made better by agents who are genuinely able to guide both buyers and sellers towards a mutually rewarding outcome.
With calmness, confidence and conviction. With a depth of knowledge that can’t be Googled, and clarity of judgement that’s impossible to fake.
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First published in PrimeResi, 27 July 2026.
