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  • Writer's picturejeff1633

Josh Flagg, Million Dollar Negotiator

Updated: Oct 13, 2023

I recently sat down with Josh Flagg, star of TV show - Million Dollar Listing.

The ability to negotiate is a key skill that all great leaders possess. But what exactly are the qualities that enable and empower the very best negotiators? And why are they so important?

I recently read an advance copy of an immensely practical and entertaining book called The Deal: Secrets for Mastering the Art of Negotiations by Josh Flagg. Believe it or not, Flagg is the longest-tenured cast member of the Bravo series Million Dollar Listing.

To those unfamiliar with the hit TV show, it follows several hand-selected and highly charismatic real estate agents who are responsible for helping clients buy and sell the most coveted properties in Los Angeles - we're talking about multi-million-dollar estates in Beverly Hills, Malibu, and Hollywood. Negotiations are high-stakes and very, very emotional.

After reading Josh's book I wanted to pick his brain a little more, so I invited him to share his negotiation secrets with me in a one-on-one interview. He accepted.

On the surface it's easy to attribute his negotiating prowess to charm, experience, and a deep knowledge of the Los Angeles real estate market. But after sitting down with him and really peeling back the onion, it's clear that there are a handful of "soft skills" and "intangibles" that enable him to rise above the rest.

I'm absolutely convinced that many of these same soft skills are also essential for leadership and are indeed what separate the "merely good" from the truly great modern-day leaders in our society. These vital soft skills include judgment, empathy, self-awareness, authenticity, adaptability, resilience and of course, integrity. Let's talk about each of them.


In every city and town across America, the real estate market is constantly changing. Brokers are swimming - perhaps drowning - in information, sales transactions, new offers, and broken deals. Nowhere is this truer than in big cities like Los Angeles and New York. The best dealmakers can quickly and effortlessly cut through this clutter, separate the wheat from the chaff, and zero in on the most important pieces of data. Immediately, this gives the negotiator the upper hand. Knowledge is power.

Savvy negotiators can make sense of the most salient issues and deal points and go on to ask insightful follow-up questions. Judgment allows the million-dollar negotiator to see the whole chess board and clearly anticipate future moves and unintended consequences.

Judgment also allows the negotiator to help clients make tough tradeoffs and more effectively prioritize key deal points. Without good judgment a dealmaker will see the world in a more myopic, disconnected way and decision making will be more reactive than strategic.


Possessing the ability to really put yourself in the shoes of another individual and understand where they're coming from (their feelings, thoughts, and underlying agenda) is a key requirement for million-dollar negotiators. When I spent time with Josh Flagg, it was clear that he had two distinct levels of empathy. On the surface, Flagg had what I would call cognitive empathy: the ability to clearly understand what buyers and sellers are thinking.

But at a deeper, and perhaps more important level, Flagg had emotional empathy: the ability to understand - or even feel - what buyers and sellers are feeling in the heat of the moment. Armed with that kind of deep, psychological awareness, Flagg can custom tailor his words - and even his body language - in a way that truly resonates with a wide range of constituents. Here I must make an important distinction.

Emotional empathy should not be mistaken for its first cousin, compassion. The latter, if taken to the extreme, can prevent a million-dollar negotiator from making tough decisions, particularly when undesirable interpersonal decisions need to be made which might cause some feelings to be hurt and bad deals to be begrudgingly made.

Self-Awareness and Authenticity

If empathy is the outward-looking part, there's also an internally focused component that all million-dollar negotiators possess. It's called self-awareness. "Know thyself," as Socrates famously said thousands of years ago. Master negotiators spend a great deal of time doing the hard work and reflection to get in touch with how they think and feel, and to discover what motivates them at the negotiation table. This level of self-awareness is also a fundamental prerequisite to authenticity.

Paradoxically, the more complex and contentious the negotiations become, the more essential it is to be absolutely clear about who you are, how you feel, and where your "true north" lies. For example, Flagg was able to clearly articulate his core values, and how they were influenced by his Grandma Edith, a woman who always spoke her mind, treated others kindly, and punched way above her height and weight.

Self-knowledge creates more authentic interpersonal connections - because people trust you - which in turn create a smoother negotiation process. The exact opposite would be embodied in the prototypical "used car salesman" who is motivated purely by the transaction.

Finally, authenticity fosters one's openness to new perspectives, ways of thinking and points of view. Such broad-mindedness can lead to creative solutions when intractable deal points rear their ugly heads.


One of the most common derailers of otherwise talented and successful negotiators is the fact that they've become set in their ways; they think they know everything, and they've seen it all before. Essentially, this boils down to a lack of self-awareness, myopia, and perhaps even delusion about one's own value at the negotiation table. In the face of a multitude of options and no clear path to a "done deal," the capacity to adapt is thrown into stark relief. Million-dollar negotiators are able and willing to change direction when required - regardless of what's worked in the past. Flagg mentioned several times that every single deal is unique. One should appreciate history, but not be shackled by it. A good negotiator knows there are situations, particularly when the external context has significantly changed, when it is necessary to adapt. Digging in one's heels and "standing their ground" is a dangerous, often fatal flaw in these fast-moving situations.


Even when the million-dollar negotiator makes all the right moves, unexpected obstacles will inevitably emerge along the way. As the legendary heavyweight boxer Mike Tyson once said, "Even the best strategy flies out the window when you step into the ring and get hit in the face." All negotiators - even Josh Flagg and his closest colleagues Josh Altman, Tracy Tutor, and Fredrik Eklund - take their fair share of punches too, and sometimes fall to the mat. It's a combination of passion and resilience that allows them to get back up and fight. Indeed, Flagg openly admits that, "a little bit of healthy competition raises all of our games."


Nothing else matters if the negotiator lacks integrity. It's the foundation that keeps the whole structure standing upright. Remove integrity and the house of cards will eventually come tumbling down no matter how smart, empathetic, and emotionally aware a leader may be. In that sense, integrity is the single most important leadership quality.

In negotiations there are always shades of gray and ample opportunities to take the easier, less ethical route. Million-dollar negotiators aren't tempted to stray down this shady path. After all, the only thing any negotiator - or leader or human being for that matter - have in the long run is their reputation. It takes years, or even decades to build it, but only minutes of poor decision-making to lose it forever.

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