There’s a general consensus that to develop a legal tech strategy, you need to follow four steps: identify what you have (your systems, workflows, pain points), map the gaps, define the solutions, and implement them.
The four steps are good. They are in the right order, and I would not recommend skipping any of them. But in project after project, this process produces strategies that look good on paper, but don’t deliver in practice. Not because the analysis was wrong, but because the strategy answers “what do we need to do?” but ignores the more important question, “are we capable of doing it?”
The failure rate in legal technology projects is not primarily a technology problem. There is plenty of good technology out there (arguably, too much), and a lot of it works well and solves a genuine pain point. What breaks down is everything around it: the organisational factors that determine whether a transformation succeeds or fails. Five of these factors come up consistently in the programmes I have worked on, and almost none of them appear at the beginning of the standard four-step process.
Matching desire to capability
Before starting any technology project, there is a question that needs asking: is the organisation genuinely capable of the change it is planning? A legal technology transformation requires time, resource, and sustained focus from the people running it. It requires a cross-functional team with the skills and experience to manage vendor relationships, lead requirements processes, implement the technical aspects, drive adoption, and hold the programme together through the inevitable complications.
If those skills are not in the team today, the plan needs to account for that, not as an afterthought, but as part of the design. If ambition doesn’t match capability, the gap between them becomes the first risk.
Defining success upfront
What does success actually look like? Not in general terms. Specifically. In twelve months, if this goes well, what is different? What is the business expecting to be true?
Legal technology programmes that miss out this question find themselves a year later unable to answer whether it worked, which makes it very hard to maintain stakeholder support, justify further investment, or learn from what happened. Defining success criteria before you start is not bureaucracy. It is the thing that keeps everyone aligned when decisions get harder mid-implementation, and it is the foundation for defining ROI, building a business case and securing budget.
Change management and tech fatigue
Change management is the element most consistently underestimated in all transformation programmes. It is easy to include it as a line in the project plan. It is harder to honestly assess the change conditions you are actually operating in.
I ran two AI contract review pilots with a team. They were structured, properly supported, with real evaluation criteria. Unfortunately, each tool had genuine strengths but neither was the right choice. When I stepped back, the team attempted a third pilot on their own, but it never really got off the ground. Not because the tool wasn’t good enough, but because two rounds of inconclusive results had left the team feeling under-confident that any tool would deliver (and without external support driving it, BAU took over and the initiative stalled).
That is tech fatigue in practice: not cynicism, but low expectations borne of experience. Recognising it honestly, and adjusting the pace, the communication, and the approach accordingly, is the difference between a well managed change programme and a process that leaves people frustrated.
Stakeholder alignment
Legal technology does not exist in isolation. Implementation typically touches IT, procurement, finance, and multiple business lines. Those functions need to be bought into the strategy, not just informed of it.
There is an important difference between stakeholders who understand what the project is trying to achieve and why it matters for them, and stakeholders who have simply been told it is happening. I have seen a CLM implementation where a key business stakeholder was nominally behind the project (present at the kick-off, supportive in principle) but never sufficiently aligned to protect it when things got hard. When opposition arose within their team, they were the first to authorise exceptions to following the process. While we were able to get things back on track, it did hinder progress and a lot of the problems that followed would have been avoided if that function had been more meaningfully involved from the start.
Getting alignment early is more than just communicating. It means making sure key stakeholders understand the specific asks of their team, have a genuine say in how the system or tool is designed, and have enough skin in the game to advocate for it even when their people push back. That investment at the front end is what determines whether the programme survives contact with the rest of the organisation.
Transformation risk
The one question I rarely hear is “what happens if it doesn’t work?” Every technology project carries risk, and most of them have a risk register. What they don’t spend enough time on is an honest assessment of the specific conditions that could cause those risks to materialise – and a clear view of what happens if they do.
Does the business have a contingency? Is there a decision framework for when to pause or change direction? Thinking through the failure modes before they happen is not pessimism. It is good governance. And organisations that do it make faster, better decisions when complications arise (which they always do).
What this means in practice
These five elements don’t replace the four-step model. The assessment still needs to happen. The gaps need to be mapped. The solutions need to be defined and implemented. But treating these five questions as foundational work, addressing them before the strategy takes shape, not half-way through the project, changes the outcome.
A legal technology strategy built around your actual change readiness, with clear success criteria, realistic change management, genuine stakeholder alignment, and an honest view of the risks, is a very different thing to one built on the assumption that organisational readiness is a given.
The technology rarely fails. The transformation around it does.
If you are scoping a legal tech strategy and these questions have not come up yet, raise them now. It is almost always easier to work through them at the design stage than to unpick the consequences twelve months in.
Rethink Legal works with in-house legal teams at exactly this stage – before the strategy is locked and while there’s still time to build the right foundations.
Find out more about our Consulting Services.
