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Real Estate Leaders Must Ask ‘Why Won’t People Do It?

Published on 27/10/2026 • By Chloe Turner

Real estate principals often face frustration when introducing new ideas to their teams, only to be met with resistance from agents who are hesitant to adapt. This resistance can stem from various sources, including the introduction of new tools such as customer relationship management software, artificial intelligence-powered prospecting tools, or alternative methods for managing buyers and vendors. Despite the apparent benefits of these innovations, some agents may continue to rely on traditional methods, leaving principals wondering why their teams are not adopting the changes.

Dreamers versus Detectives

According to organisational change consultant Philip Jameson, this frustration can actually hinder a leader’s ability to effect change. In his TED Talk, “Want someone to change? Ask this question,” Jameson argues that successful change begins with understanding the obstacles that prevent people from adopting new approaches, rather than simply assuming they should recognise the benefits. This distinction is particularly relevant in the real estate industry, where experienced agents often have established methods and strong opinions about what drives results. Jameson identifies two approaches to leading change: the “dreamers” and the “detectives.” Dreamers are convinced that their proposed improvements are superior to existing methods, while detectives investigate the obstacles that might prevent people from adopting new approaches.

The key difference between these two approaches lies in the questions they ask. Dreamers ask, “Why wouldn’t people do it?” whereas detectives ask, “Why won’t people do it?” This subtle shift in thinking can have significant implications for how real estate agencies introduce new systems, manage performance, and build stronger teams. For instance, an agency principal who invests in a sophisticated customer relationship management system may expect agents to adopt the new technology, but an established agent may be hesitant due to concerns that the system will make their interactions less personal or require significant time to learn.

Simply reiterating the benefits of the new system is unlikely to alleviate these concerns. Instead, Jameson suggests that leaders should seek to understand what agents believe they will lose by adopting the new approach and address those concerns directly. A case study from Jameson’s TED Talk illustrates this point. A hotel chain introduced a new pricing tool that utilised automation and machine learning, but employees were sceptical because they trusted their own pricing instincts more than the technology. Rather than forcing staff to use the system, the organisation involved experienced employees in an early user group, demonstrating the tool’s value and effectiveness.

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This approach can be applied to real estate agencies, where involving respected senior agents in the introduction of new technology can be more effective than simply expecting everyone to accept a management-level decision. An experienced salesperson who has tested a system and found it useful may carry more influence with colleagues than a presentation outlining the system’s potential benefits. It is also essential to distinguish between agents who refuse to change and those who lack the time, confidence, or training to do so. Jameson encourages leaders to investigate whether employees have the necessary knowledge and skills, whether practical obstacles are hindering change, and whether they believe they have something to lose.

Overcoming Common Obstacles

In a real estate office, these obstacles can be surprisingly ordinary. An agent may understand the value of detailed buyer records but struggle to find time to update them between inspections, negotiations, and appointments. A property manager may support a new communication process but feel overwhelmed by the additional administrative work involved in learning it. In such cases, the solution may not require another meeting about compliance or efficiency but rather providing better training, simplifying the process, or allocating time for people to become comfortable with the new approach.

Understanding the other side

More complex barriers can emerge when change affects someone’s sense of expertise, independence, or status. For example, a high-performing agent who has built a successful career using a particular listing presentation may interpret a new company-wide approach as a suggestion that their existing methods are inadequate. Similarly, an experienced sales manager who has always controlled certain decisions may feel that introducing automation diminishes their role.

These concerns are not necessarily arguments against change but can help explain why capable, committed employees sometimes resist it. Jameson emphasizes that leaders need to investigate these underlying motivations rather than dismissing them. As he notes, “When people feel they don’t gain anything by changing, or worse, when they feel that they have something to lose, we shouldn’t be surprised when they don’t change at all.”

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This perspective suggests that successful leadership involves more than identifying the right business strategy; it also requires understanding how that strategy will be experienced by the people responsible for delivering it. The same thinking can be applied beyond internal management, as agents regularly encounter resistance when advising vendors to adjust their price expectations, reconsider a marketing strategy, or accept changing market conditions. An owner who refuses to reduce their asking price may not simply be ignoring comparable sales; they may be concerned about the implications of a lower result for their next purchase or worried about appearing to have made a poor financial decision.

Applying the strategy externally

Repeating market evidence may be necessary, but understanding the reason behind the owner’s position can make the conversation more productive. Likewise, a buyer who appears unwilling to improve an offer may have genuine financial limitations, uncertainty about future interest rates, or concerns that have not yet been discussed. The lesson for agents is not to abandon professional advice or avoid difficult conversations but to recognize that persuasion becomes more effective when it begins with understanding.

Three Steps to Encourage Change

Jameson offers three practical suggestions for encouraging change. The first is to ask people directly what is preventing them from adopting a new approach, rather than relying on assumptions. The second is to ask more than once, recognizing that deeper concerns may only emerge after more immediate problems have been addressed. The third is to avoid turning resistance into a judgment about someone’s character.

As Jameson notes, “When people aren’t behaving the way you expect, it’s tempting to say that they’re lazy or resistant, but moralizing doesn’t help you get the thing that you want: a successful, sustained change.” This is particularly relevant in an industry where performance expectations are high, and agency leaders are often under pressure to improve productivity, protect margins, and respond quickly to changing market conditions.

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