3 Keys to Successful Dealmaking: Empathy, Courtesy, and Respect

Amy Hall, COO, Caton Commercial Real Estate Group

Amy Hall, COO, Caton Commercial Real Estate Group

Caton Commercial Real Estate Group provides a wide spectrum of commercial real-estate services - commercial property services, investment sales, land development services. Caton also caters to international clientele and provides consultative services to municipalities.

As head of Caton’s day-to-day operations and growth initiatives, Amy Hall is the first to tell you, her industry is competitive, male-dominated, and laced with a hard-driving, get-the-deal-done focus.

Nonetheless, “there’s probably no more important trait that I have than to treat people well.”

Amy is quick to add that she’s no pushover, nor does she tolerate or condone disrespectful behavior. “At all times, it’s extending professional courtesy and respect in order to understand how we can best get to a meeting point.”

While she has seen others around her use manipulation and bullying as ways to get to a deal, Amy’s business philosophy is steeped in how she was raised with the golden rule, “Treat people the way you want to be treated.”


“One of the greatest learnings of my early career was that others have their own working style. We must acknowledge differences and communicate in a way so that they can hear what we are saying. That is truly leaning into professional respect.”


Set against the “hard-driving” backdrop of commercial real estate, the softer deal-making practices of empathy, courtesy, and respect can be a hard sell (pun intended). Amy knows that. She uses them as tools to decipher the intent behind what those sitting across the table are saying, to get both sides to a meeting point. After generating hundreds of millions of dollars in value through successful real estate negotiations and leading dozens of sales staff over the years, she explains that “Empathy is about solutions.” She further explains that only when you can look at a situation from their perspective do you really become an exceptional dealmaker or leader.

Every step of the way, she’s confirming what she’s thinking. “Have I looked at it from their perspective? Have I put myself on their side of the table? Do I truly understand their motivation?” In the process she goes to the source to seek out additional information.

“My quickest way to understand is seek clarification around their point of view on the situation,” she says. “You don’t know what someone else is thinking unless you ask. If you do not ask, you assume.” You quickly get why this is key for her because making assumptions can lead to not-so-good deals or no deals at all.

By asking good questions, she’s able to get answers that fill in their intentions. “Empathy is a professional courtesy. Put yourself in someone else’s shoes, in every step of your relationship, and stay out of the place of assumption. Ask questions.” Her empathetic approach translates assumptions into knowledge and successful deals.

Throughout the years of training, mentoring, and managing real estate sales professionals, Amy has encountered countless examples of how a lack of empathy and understanding has negatively impacted results. “Assumption in deal making is typically deal breaking and if you don’t care enough to find out the facts, then you don’t care enough to get the deal done.”

One example of this was a dealmaker who was negotiating to lease a space within an enclosed shopping mall. The prospect operated a space in a neighboring stripmall center. The shopping mall space and the prospect’s current space had different operating hours.

In a desire to “get the deal,” the dealmaker made an assumption. What was it? That the prospect knew the operating hours of the mall.

The negotiations advanced. Then, at the point that the prospect was reviewing the agreement with their attorney, the deal fell apart. The prospect discovered that they would have to be open during mall hours. But it couldn’t be done, they did not have the budget or the staff to absorb the additional overhead.

Weeks of time, energy, and legal fees were wasted due to an assumption. The young dealmaker knew there was a difference but chose not to delve further or offer up any additional information. The dealmaker did not care enough to look at the situation and say, “I know this prospect only operates from 10 a.m. - 5 p.m. six days per week. The mall operates from 10:00 – 9:00 p.m. six days a week and 11:00 a.m. – 6:00 p.m. on Sundays. This is an increase of more than 1,600 operating hours per year.” The dealmaker did not ask clarifying questions like, “Have you looked at the additional cost of doing business in a mall?  Will you need to add additional staff? What type of sales increase is needed to cover the increased overhead? Is that increase really possible?” When you ignore the challenges faced by the person on the other side of a conversation, often everyone loses.


For Amy and her team, there is one clear factor for success - empathy. “It is an incredible and invaluable trait in the workplace to embrace. It leads to excellence.”



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