5 critical legal AI discussions to prioritize at Legalweek 2025

Legalweek is your chance to explore what's next in legal technology, discuss developments with peers, and identify solutions worth bringing back to your team. But with hundreds of vendors, dozens of panels, and just 48 hours to navigate it all, you need a strategic approach to maximize your time and return with actionable insights rather than just business cards.

At DraftWise, we've been fortunate to work alongside the world's preeminent legal minds—from Vault 10 practice leaders to Fortune 100 general counsel. At the intersection of legal excellence and technological innovation, we have unique insight into what's driving attorney tool adoption and firm strategy today.

We've learned that behind the AI hype are real, transformative opportunities for transactional practice—if you know what to look for. The difference between game-changing implementation and expensive disappointment often comes down to asking the right questions at the right time.

To help you cut through the noise at Legalweek, focus on these five critical questions when evaluating AI vendors:

1. ROI focus: "How are peer firms measuring ROI from their generative AI implementations in transactional practice?"
2. Data usage: "How does your solution incorporate our existing precedent when generating suggestions?"
3. Seamless integration: "Does your tool require switching between applications or can attorneys access all capabilities within their existing drafting environment?"
4. Specialized knowledge: "How does your AI model handle transaction-specific concepts like defined terms and cross-references?"
5. Security standards: "Where specifically is client data stored when using your AI capabilities?"

For each of these topics, we’ll explain why it’s crucial to ask these questions as you evaluate your options for AI solutions at Legalweek. For deeper look into hese topics, join our Chief Customer Officer Will Seaton's panel on "Which LLM is Right for Your Firm? Choosing the Right LLM for Data Optimization in Legal Practice" at Legalweek on March 26th at 2:00 PM.

1. Generative AI is transforming transactional practice

Generative AI (GenAI) is no longer just a buzzword in legal tech—it’s a lasting tool changing how transactional attorneys draft, markup, and negotiate their contracts. Early adopters of legal AI already see radical efficiency gains—drafting complex agreements in a fraction of the time while maintaining precise control over language and risk profiles.

Understanding what problems you should solve with AI can be daunting. Start by thinking about the various mundane tasks and inefficiencies that riddle the contract cycle and where a tighter process could positively impact the client. Tools that enhance rather than compromise your firm's unique approach to drafting and negotiation can create powerful results for transactional teams. 

Questions to ask contract AI providers at Legalweek:

• How are peer firms boosting ROI from generative AI implementations in transactional practice?
• Which practice groups or contract types see the most value from generative AI?
• How quickly can you expect tangible results after implementing AI-powered drafting tools?

2. Your precedent is your competitive advantage

While generic AI models may offer basic drafting capabilities, true competitive advantage comes from leveraging your firm's collective knowledge. Your existing precedent library represents years of refinement and client-specific language that generic models simply cannot replicate.

Law firms sit on mountains of data, and activating this proprietary precedent allows you to tap into AI’s efficiency-driving power while ensuring all suggestions remain firmly grounded in your firm’s established practices and style guidelines.

Questions to explore at Legalweek on how AI can utilize legal knowledge:

• How does your solution incorporate our existing precedent when generating suggestions?
• Can your system distinguish practice group-specific or client-specific language patterns?
• What controls do you offer to prioritize specific precedents or exclude sensitive matters?

3. Integration with core applications is non-negotiable for attorney adoption

Your attorneys already navigate multiple systems throughout their day. Adding another standalone tool creates friction that undermines adoption, regardless of the tool's capabilities.

Look for solutions that meet attorneys where they already work. The most successful implementations integrate directly into familiar environments like Microsoft Word and your document management system, minimizing learning curves and maximizing productivity from day one.

Questions to ask about integration at Legalweek:

• How does the tool integrate with your existing document management system and drafting ecosystem?
• What is the typical learning curve for attorneys of different technology experience levels?
• Does the tool require switching between applications, or can attorneys access all capabilities within their preferred drafting environment?

4. Transaction-specific AI outperforms general models

Legal work demands precision that general-purpose AI models cannot deliver.  Transactional practice, in particular, involves complex concepts like defined terms, cross-references, and regulatory requirements that general models frequently mishandle.

At Legalweek, distinguish between vendors using off-the-shelf models versus those who have developed or customized AI specifically for transactional use cases. The difference dramatically impacts accuracy, reliability, and the amount of human review required.

Questions to ask about AI specialization at Legalweek:

• How does the vendor's AI model handle transaction-specific concepts like defined terms and cross-references?
• Can the system recognize and appropriately handle different types of agreements and their unique structural requirements?
• What safeguards prevent the system from generating legally problematic suggestions?

5. Security and control are table stakes

Client confidentiality remains essential, regardless of technological advancements. Firms cannot afford to compromise on data security in pursuit of efficiency gains. As you explore AI solutions at Legalweek, security and control should be non-negotiable baseline requirements.

The most sophisticated legal AI providers understand these concerns and have built platforms with rigorous security controls, including data security protocols and deployment options that align with client confidentiality needs. Don't hesitate to ask detailed security questions—reputable vendors expect and welcome this scrutiny.

Questions to ask about security at Legalweek:

• Where specifically is client data stored when using the vendor's AI capabilities?
• What control mechanisms allow you to restrict certain matters from AI training or suggestions?
• How does the vendor handle security and compliance certifications relevant to legal practice?

How DraftWise can help 

DraftWise is an AI contract drafting, review, and negotiation platform powered by your legal knowledge. Vault 10 firms using DraftWise see 15-20% higher realization rates on transactional matters.

Unlike general-purpose AI tools, DraftWise was built from the ground up for legal drafting workflows. We integrate directly with Microsoft Word and your document management system, providing AI-powered assistance precisely where your attorneys already work. Our customers report up to 30% time savings on contract review while maintaining or improving quality standards.

We're excited to show you how your firm can achieve similar outcomes by using your institutional knowledge to streamline your contract process without compromising quality.

Connect with DraftWise at Legalweek 2025

To explore these themes further, join our Chief Customer Officer, Will Seaton, for his panel discussion on "Which LLM is Right for Your Firm? Choosing the Right LLM for Data Optimization in Legal Practice" at Legalweek on March 26th at 2:00 PM. Will brings firsthand insights from working with the world's top firms on successful AI implementation strategies.

You can also connect with the DraftWise team at:

• Booth #3003 in Americas Hall 2 for personalized demonstrations
• Our exclusive breakfast at La Grande Boucherie on March 26th (RSVP here)
• Our Morning Run with Ari Kaplan on March 26th (Register here)
• Book a time to meet with our product experts (Book here)

We look forward to continuing these conversations at Legalweek and showing you how DraftWise is helping lawyers leverage AI to transform transactional practice.

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