Strategies to Increase Lawyer Adoption of Legal Software

What separates tech-savvy lawyers from those being left behind: 1. Start with problems, not tools. - Identify your most painful daily bottlenecks before exploring software solutions - Ask "what takes me 3+ hours that should take 30 minutes?" rather than "which AI should I buy?" - Focus on fixing specific workflows instead of chasing trendy platforms - Audit how many times you repeat the same tasks manually each month - those are your automation targets 2. Invest in practical learning. - Schedule 30 minutes weekly to master one feature of tools you already have - Join user communities for your key platforms - they're goldmines for shortcuts - Record short videos of your improved processes to share with skeptical colleagues 3. Measure what matters. - Track time saved through automation, not just money spent on subscriptions - Document how tech adoption has improved client response times - Collect specific examples of errors prevented through better systems - Calculate your "not having to ask IT" dividend - the hours saved by becoming self-sufficient The most effective legal tech adopters aren't necessarily technical experts. They're pragmatic problem-solvers who recognize that a contract management system that works is worth more than another hour spent manually checking defined terms. They've learned that time invested in mastering technology pays dividends in every matter that follows. #legaltech #innovation #law #business #learning

Last week at LegalTechTalk, I moderated a closed-door roundtable on AI with 10 innovation leaders from leading law firms across the US, UK and Europe. Here are my top 3 key takeaways from the conversation: 1/ Targeted use cases over firm-wide rollout - Firm-wide rollouts rarely result in massive adoption. One US-headquartered law firm shared that after their initial firm-wide rollout of Gen AI, they only had adoption from 10-20% of the firm. - There is a spectrum of tools emerging on the market from general-purpose microwaves to specialised pizza ovens and expert personal chefs. It’s about knowing which kind of tool is best suited for which use case and context. - Focusing on targeted and concrete use cases is the best way to prove value by showing (instead of telling) success and getting wider buy-in across the firm, and to bring on board sceptics. 2/ We sometimes forget that lawyers are humans - It’s difficult to get lawyers to leave the tools they are already working with and are familiar with. One innovation leader shared that vendors who are embedded into Outlook and Word make it easier to drive adoption. - Creating a network of AI Champions and focusing on peer-to-peer learning with knowledge sharing and social learning is a better way to create energy and convert colleagues to use AI instead of endless training sessions. - Most of the firms shared that there were AI sceptics inside their organisation. A large part of their role is consensus-building and navigating the politics of the partnership. It’s a far better use of resources to work with the willing and win the naysayers with proof of success. - AI fatigue and overwhelm are real. It’s impossible to run pilots with lawyers to test every single vendor on the market. It’s more effective to filter down on a specific use case in a practice group and find vendors who can solve that problem. 3/ Vendor Proliferation - A sea of sameness? - There is an endless list of vendors flogging AI in legal to innovation teams, meaning that the signal isn’t clear from the noise. - Most of the vendors have massive overlaps in features and capabilities, leading to redundancies in purchasing multiple solutions. It also raises questions for innovation leaders about what value vendors add above the core LLMs they use. - One innovation leader at a billion-dollar law firm shared that vendors need to think about decoupling back-end AI functionality from the front-end interface so firms can purchase what they need from different vendors and construct a unified single interface for lawyers. The roundtable was sponsored by DeepJudge. Massive thanks to Timothy Sulzer and Lukas Reichart for sharing their perspectives and to the team at LegalTechTalk for the opportunity to moderate the discussion. What would you add?

If you are a lawyer, whether in a law firm or an in-house legal department, here are the questions you should be asking about legal tech and innovation: 1) Do you start with the client or business? • For firms: does your tech roadmap improve client experience and value? • For in-house: does it make your business stakeholders’ lives easier, faster, safer? • Can you clearly link each initiative to better service, speed, or risk management? 2) Are people and process ahead of the tech? • Have you fixed the workflow before adding a tool? • Are lawyers and staff trained, incentivized, and supported to change how they work? • Or are solutions gathering dust because the process gap was never addressed? 3) How strong is your adoption muscle? • Who actually uses the tools in daily work? • Do you have structured change management or only isolated pilots? • Have you learned from failed implementations and applied those lessons? 4) Do your leaders role model innovation? • Do they use and talk about technology in delivery or decision-making? • Are they preparing for second order effects like: - Training juniors differently as traditional tasks get automated - Rethinking time based billing or productivity measures - Developing new service lines or risk frameworks - Setting standards for ethical and responsible AI 5) Who are your internal champions? • Which lawyers or professionals are experimenting and sharing wins? • Do you showcase their success to inspire others? • Are you building a pipeline of digitally fluent next generation talent? 6) Can you demonstrate ROI and impact? • For firms: can you show hours saved, revenue protected, client satisfaction gained? • For in-house: can you show faster contract cycles, reduced risk, or business enablement? • Do your stakeholders, internal or external, feel the difference innovation makes? If you cannot answer these questions with confidence, your legal tech strategy may not be working for you. Picture Courtesy - The amazing Leila El Gharbi

The secret to winning over lawyers (Hint: Don’t try) If you’ve ever tried to introduce a new process, tool, or way of working to a legal team, you know the struggle. Some lawyers are open to change. Others? Let’s just say they’d rather redline an MSA for sport than embrace a new workflow. Here’s what I learned handling Legal Ops at Meta and Coinbase: Trying to force change is a losing game. The trick? Don’t push – let their peers pull. Instead of wasting time convincing the holdouts, build trust with early adopters first. Once they start using a new system and seeing results, the skeptics won’t want to be left behind. How to Make This Work in Legal Ops: ➜ Find your champions Identify the lawyers who are open-minded. They’re your biggest allies. Get them using the new tool or process first, and let them prove it works.  I take the same approach with initiatives from the COO’s office at SpotDraft. ➜ Start small, show wins Don’t roll out massive changes all at once. Start with a specific team or contract type, track improvements (faster turnaround, fewer errors, etc.), and broadcast the success. ➜ Make it a no-brainer Lawyers resist change because they think it’ll slow them down. Make it impossible to ignore the benefits – faster contract cycles, fewer headaches, less back-and-forth. When they see their peers getting through work more efficiently, FOMO kicks in. ➜ Let the business teams speak Sometimes, legal won’t listen to legal. But when sales, procurement, or finance start praising the new system because deals are closing faster? That’s when holdouts start paying attention. ➜ Turn skeptics into advocates Once a previously resistant lawyer starts using the new system and sees results, celebrate their success. Make them the spokesperson for the change. Lawyers trust their own more than an ops person telling them what to do. At the end of the day, lawyers don’t hate change – they just hate being forced into it. Tried this approach before? Let me know what worked (or didn’t)! #LegalOps #Leadership #LegalInnovation #LegalTech

What if I told you that most law firms buying AI tools today aren't actually using them? That conversation I keep having with law firm partners is becoming increasingly common. They're investing in expensive technology platforms, announcing them with fanfare, then watching usage rates stay near zero six months later. It's not a technology problem. It's a culture problem. I've been observing this pattern across the industry for months now. Firms are under pressure to appear innovative, so they purchase cutting-edge AI tools. But then reality sets in. Partners who built their careers on traditional methods are skeptical. Associates realize these efficiency tools actually hurt their billable hour targets. The expensive software sits unused while everyone goes back to the old ways of working. In the second article of my four-part series "Remaking the Model: A Blueprint for Law Firm Culture Transformation," I explore how three specific technological forces are creating unavoidable friction with traditional law firm structures. From the economic tension between AI efficiency and billable hour models to the way cloud collaboration is flattening hierarchies that took decades to build. The most successful firms aren't just buying better technology. They're fundamentally rethinking their incentive structures. Instead of only rewarding billable hours, they're experimenting with efficiency bonuses, client satisfaction metrics, and profitability measures that actually encourage technology adoption. They're aligning their internal rewards with the value their clients expect. What's particularly interesting is how some firms are discovering that AI's real value isn't in making old processes faster, but in completely reimagining how work gets done. Instead of having AI review contracts the same way humans do, they're creating entirely new workflows where AI handles pattern recognition while lawyers focus on strategic advice and relationship building. It's a shift from automation to transformation. What I'm seeing consistently is that this transformation requires senior leadership to actively champion change rather than delegating it to IT departments. Managing partners and practice group leaders need to model the behavior they want to see, using these tools themselves and publicly celebrating efficiency gains rather than just billable hours. I also share the story of fictional "Cromwell & Finch" and their AI contract review platform disaster. It's a scenario I'm hearing variations of everywhere, where internal resistance meets external client pressure and something has to give. The firms navigating this transition successfully aren't treating this as an IT issue. They're investing in change management, appointing technology champions in each practice group, and using their own data to drive decisions rather than assumptions. The pace of change feels different this time, and the implications often aren't clear until after they've happened.

77% of in-house lawyers have experienced a failed legal tech implementation. One way to avoid this is to dodge big all-in-one solutions. Don't buy a Swiss army knife if you only need a bottle opener. But even when you're looking at tools that solve just one problem, some are easier to use than others. Two main factors affect this: • 𝗛𝗼𝘄 𝗺𝘂𝗰𝗵 𝗱𝗼 𝘄𝗲 𝗻𝗲𝗲𝗱 𝘁𝗼 𝗰𝗵𝗮𝗻𝗴𝗲? Every tech tool will on some level change how your team works. But the best tools minimise this. They know that for every change, implementation will take longer and fewer team members will end up adopting it. • 𝗛𝗼𝘄 𝗶𝗻𝘁𝘂𝗶𝘁𝗶𝘃𝗲 𝗶𝘀 𝗶𝘁?    Think about consumer apps like Uber. No one expects to spend an hour learning how to use it. But many business tools require hours of training. The more intuitive a tool is, the more likely your team will use it. 𝗥𝗲𝗮𝗹-𝗪𝗼𝗿𝗹𝗱 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: 𝗖𝗼𝗻𝘁𝗿𝗮𝗰𝘁 𝗥𝗲𝗱𝗹𝗶𝗻𝗶𝗻𝗴 𝗧𝗼𝗼𝗹𝘀 Let's say your team is struggling with contract reviews. You might look at AI-powered redlining tools. But even among these, there's a spectrum: 🤔 Some require you to upload contracts to the browser, to get the redline suggestions there. That means your team now have to get used to marking up in a new browser based editor instead of Word. 🤔 Some will require you to spend months ‘training’ the AI to get accurate results, instead of it working out-of-the-box. The best ones will show up right inside tools your team already uses, like MS Word. 𝗪𝗵𝗮𝘁 𝘁𝗼 𝗹𝗼𝗼𝗸 𝗼𝘂𝘁 𝗳𝗼𝗿 𝗶𝗻 𝗮 𝗱𝗲𝗺𝗼: 1. 𝗪𝗼𝗿𝗸𝗳𝗹𝗼𝘄 𝗰𝗵𝗮𝗻𝗴𝗲𝘀: Try to be aware of every workflow change that would be required to use the tool. List these out knowing that every change is something your team will question, debate, and get annoyed about!     2. 𝗗𝗼 𝗜 𝗴𝗲𝘁 𝗶𝘁? Ask yourself, do I understand how this works within 1- 5 mins? If not, my team won’t either and they likely won’t bother trying to learn it (they simply won’t find the time).     3. 𝗖𝗮𝗻 𝗜 𝘁𝗲𝘀𝘁 𝗯𝗲𝗳𝗼𝗿𝗲 𝗜 𝗰𝗼𝗺𝗺𝗶𝘁? Make sure you can try out the tool in a small way before rolling it out to everyone. I really believe the future of legal tech isn't about having the most complex tool. It's about having the right tools that your team will actually use and love! --- 𝗣𝗦 / 𝗦𝗮𝗹𝗲𝘀 𝗽𝗶𝘁𝗰𝗵: At DraftPilot, we face these trade-offs every day. We made a key decision: everything must work in the Word add-in, so you get all AI redline suggestions right where you work. This is hard because we have less visual 'real estate' to work with. But it forces us to be very deliberate about what features we include and keep it really easy-to-use. The benefit is that you can start using DraftPilot out-of-the-box (no implementation time), with minimal disruption to your usual workflow. If you want to give it a go send me a message! We offer a free 2 week trial (no credit card etc required).

Tech Isn’t the Strategy—Adoption Is. 🔄⚖️ Legal departments and law firms keep making the same well-intentioned mistake: assuming that buying better technology is the same as becoming a better organization. It’s not. The Above the Law article below nails this disconnect. We keep investing in smart, promising platforms—AI, contract tools, workflow engines—only to watch them sit unused. Not because they’re broken. But because adoption was never designed as part of the strategy. In too many orgs, tech procurement is treated as the win. The business case gets written, the contract gets signed, the implementation kickoff is held… and then the rollout loses steam. Lawyers, facing no clear incentives and overwhelmed by competing priorities, quietly return to legacy methods. The system may be “live,” but it’s not alive in the practice. This isn’t a tech problem. It’s a change management problem. Real legal transformation requires building adoption ecosystems: shared incentives, contextual training, cross-functional champions, and leadership that reinforces new behaviors. The best tools mean nothing if lawyers don’t see how they make their work safer, smarter, or more client-centered. If you’re investing in legal tech, invest just as heavily in what comes after: the onboarding, the narrative, the habit-building. Because innovation isn’t something you install. It’s something you cultivate. Tech doesn’t drive the strategy. Adoption does. 🔗 Full article: https://lnkd.in/gU8NmSce Comment, connect and follow for more commentary on product counseling and emerging technologies. 👇