Guest Contribution: From Kevin Bashaw, MBA, Esq., CEO of Mason
We fall in love with the promise of something new. We celebrate the breakthrough. We announce the pilot. And for a moment, it feels like progress. Then reality arrives. The recent surge of experimentation in Legal AI and Legal Technology follows this familiar arc. Many organizations that successfully deployed generative tools are now turning to more autonomous systems. They assume the next step in Legal tech is incremental. It is not. It is foundational.
When you move from AI that responds from prompts to AI that takes action, you are no longer testing efficiency. You are testing the integrity of your operating model. Legal AI systems that operate with autonomy require clarity in process, discipline in data, and alignment in accountability. If your workflows live inside people rather than systems, Legal Technology will expose that. If your data is fragmented across practice groups and platforms, Legal tech will surface that. If your incentives reward caution over ownership, Legal AI adoption will stall.
This is not a failure of technology. It is a reflection of leadership. Almost all failures of technology are rooted in a failure of leadership. When Legal AI initiatives stall, it is rarely because the models were incapable or the Legal Technology immature. It is because leaders did not align vision with execution. They did not clarify ownership. They did not prepare the culture for change. They approved the Legal tech investment but avoided the harder conversations about process discipline, data integrity, incentives, and accountability.
Technology exposes what leadership tolerates. If ambiguity, silos, and risk aversion define the organization, Legal AI will magnify those traits. If clarity, transparency, and ownership define it, Legal Technology becomes a force multiplier. The outcome is less about the sophistication of the tool and more about the courage and consistency of the people guiding it. Transformation is rarely about the tool itself. It is about whether the organization has built the operational muscle to sustain it. Legal AI does not create discipline. It demands it.
I see two predictable responses when organizations confront this shift in Legal Technology. The first is overconfidence. Leaders assume that because an early generative AI pilot performed well, expanding into more autonomous Legal tech will be straightforward. They underestimate the complexity beneath the surface. When the system encounters undocumented exceptions, inconsistent data, and human workarounds, it fails. Confidence erodes.
The second response is overcorrection. Leaders layer governance and risk controls so heavily that the Legal AI initiative becomes sterile. The pilot is technically safe but strategically irrelevant. Lawyers ignore it. No meaningful value is measured. The effort fades. Both outcomes produce the same result. Disappointment.
The organizations that will succeed with Legal AI will not be the loudest or the fastest. They will be the most disciplined. They will invest in mapping how legal work actually gets done.
They will clean and structure their data before autonomy demands it. They will align incentives so that Legal Technology is seen as an opportunity for elevation, not a threat to status.
They will treat Legal tech not as a project, but as a strategic capability.
Technology can accelerate strategy, but it cannot substitute for it. Legal AI will not transform organizations that refuse to confront inefficiency. It will amplify what already exists. It will require clarity. It will demand rigor. That may be uncomfortable. But discomfort is often where growth begins.
The real question is not whether your Legal AI pilot will struggle. The real question is whether you are willing to do the hard, unglamorous work required to make Legal Technology durable inside your organization or you will blame the lack of leadership in your law firm on the technology that you didn’t deploy properly.
Sustainable innovation in Legal tech is never about chasing momentum. It is about building a foundation strong enough to carry it.