The good, the bad, and the ugly of legal tech: practical lessons for SME law firms

In episode 29 of the Empowering Law Firm Leaders podcast, Shona discusses with Amy Bruce, marketing director at Osprey Approach, the habits and behaviours that separate the most innovative practices from the rest – and how to build momentum through small, measurable wins.

In this conversation, Shona Kaye, legal tech consultant, shares candid, first‑hand advice on why legal tech projects stumble, how to plan for success, and the practical steps SME firms can take to pivot when things aren’t going to plan.

In this conversation we cover:

• What a 5th‑century general can teach us about 21st‑century legal tech
• Why projects “fail” (and why many never get off the ground)
• How SMEs can pivot when pressure mounts
• Planning before you build: ROI, roadmaps, and readiness
• Habits of innovative, successful firms
• Choosing the right supplier – and the questions to ask

Three essentials every firm should know before investing in legal tech

Shona is clear that success with legal tech starts long before implementation. She highlights three foundational principles that every firm—regardless of size, maturity, or ambition—should understand before beginning their digital transformation journey.

1. Know the product: Shona encourages firms to pause and be “a little bit holistic” by stepping back and assessing their identity, workflows, client expectations, and long‑term goals before selecting a system. This ensures the firm chooses a product that fits its reality—not one that simply looks impressive on the surface.
2. Engage people early and effectively: Technology succeeds only when people genuinely feel part of the journey: “Understand the journey your users are going on… what will make their jobs better.” She urges firms to involve teams from the beginning through requirements gathering, workshops, and candid conversations about pain points.
3. Organisational readiness: Investing in technology is never just the cost of the product itself; firms must be realistic about the resource required to make the project successful. Shona explains that firms need to ask whether they have the right team, time, and capability internally to deliver the project well: “It’s making sure your firm actually has organisational readiness… you’re making a huge investment, potentially.”

What a 5th‑century general can teach modern law firms

For Shona, Sun Tzu’s Art of War playbook is surprisingly relevant to implementing new technology – not because tech projects are battles, but because success is planned way before go‑live. “We are on a mission when we’re undertaking these projects, and there are so many things that we need to be aware of to get them right… doing the groundwork and having the preparation.” She highlights Sun Tzu’s principle of knowing the terrain: “What’s the legal landscape? What are our clients expecting of us?” and just as importantly, “what’s our existing technological ecosystem… what would this new initiative do to those technologies?”

Shona advocates an iterative approach over big‑bang transformation: “Opportunities are multiplied as they’re seized… if we start delivering little incremental bits and getting value per department… those visible, quick wins build confidence and gain a bit of currency in your firm.” Crucially, she encourages teams to “fail fast”: experiment safely, learn quickly, and course‑correct without derailing the whole programme.

When things aren’t going to plan: pragmatic pivots for SMEs

For time‑poor, budget‑conscious SMEs, the stakes are high, but so are the options. Shona starts at source: “Plan a good product selection process” – assess fit thoroughly, review roadmaps, and don’t get sold to. Implementation success then depends on realistic resourcing: “It’s not just the cost of the tech… it’s the cost of all the resource that comes with it… build in a little bit of contingency.”

If pressure mounts, diagnose before you decide: “Get really laser‑focused on… what are these areas [of challenge]? Do we need to be technically focused? Do we need to be people‑focused?” Some blockers are integrations, others are training or change‑readiness; each demands a different remedy.

When necessary, avoid the sunk‑cost trap: “Sometimes stepping back and saying, ‘Is this working?’… If we stop our investment now, we can focus on other things.” The key is open communication with users – “people are okay if you take them on the journey”.

Shona’s experience with suppliers is they “want your feedback” and should be treated as partners, not vendors. “Don’t be afraid to pick up the phone… and if you have challenges… don’t go passive.”

Plan before you build: ROI, roadmaps, and readiness

Shona’s planning checklist is straightforward and powerful. First, mission clarity: “Who are we as a firm? What are we trying to achieve here?” Then, attach numbers: “If we are losing X because of Y… can we measure that?” Use this to build an ROI case that wins stakeholder confidence. Next, treat supplier selection as a project in itself: structured requirements, market scanning, and alignment on support and delivery methodology. Finally, run a dual‑track plan -project management + change management + business analysis, and continuously reconcile outcomes to the original ROI case.

For firms that don’t do transformative projects often, external guidance can de‑risk decisions. The aim isn’t to eliminate risk, but to surface and mitigate it early: “We’re not just going to jump on ahead. We’re going to form a really structured plan and communicate that as well.”

Habits of innovative, successful firms

Talk is cheap; experiments aren’t. Shona observes that successful firms do the work behind the scenes: “They’re not just talking about things… they’re testing things.” Leadership sponsorship is decisive, and “a culture of innovation” that permits safe trial and error encourages teams to “give things a go” and learn quickly, especially with emerging tech like AI. The goal is to start, sustain, and scale: avoid analysis paralysis and “be at the forefront of this exploration.”

Sustained success often looks like stringing together small wins. Shona cites firms that build patiently, one step at a time, without over‑stretching: “They don’t put all their eggs in one basket… little bits… all adding up to something a lot bigger.” Over the years, that compounding effect “grows massively” while keeping risk low and teams engaged.

Building confidence, clarity, and momentum in legal tech transformation

Successful legal tech transformation begins long before implementation. Firms must define what they want to achieve, understand the landscape, and select technology with intention rather than influence. Shona’s reminder to “step back” and assess who you are as a firm before choosing a product reinforces the importance of grounding decisions in strategy, not hype.

Across the discussion, people emerged as the decisive factor in whether projects thrive or stall. Engaging users early, listening to their needs, and ensuring the right skills and capacity are available creates alignment and removes friction. Shona repeatedly emphasises that momentum is built through small, well‑planned steps: testing early, iterating safely, and celebrating quick wins to build confidence and credibility across the firm.

Watch the full interview with Shona Kaye now to discover more advice and guidance on successfully implementing legal tech into your firm. You’ll also hear Shona’s exclusive advice on supplier selection and success stories of when firms have got it right and reaped the benefit of tech.