The Battle for Small Law Dominance in the AI Agent Era: Microsoft vs. Google

Microsoft dominates small law tech, but it’s fumbling the AI agent transition. Google sees the opening.

The Unexpected Opening

In most small law offices, you’ll find a familiar tech stack: Outlook, Word, Excel, Teams. Microsoft is the default productivity suite for the legal world. It has been for decades. So, when Copilot was announced, fully integrated into Microsoft 365, it seemed like the perfect AI upgrade for legal workflows.

In practice, Copilot adoption has been surprisingly slow. Most solo and small firms I speak to overwhelmingly favor AI tools like ChatGPT or legal-specific tools like Spellbook. They haven’t activated Copilot because they’re overwhelmed by its complexity, its premium pricing, and its unclear ROI.

Enter: Google.

Welcome to the AI agent showdown, where entrenched workflows meet agile innovation. This article explores the latest rollouts from Microsoft and Google and how small firms should begin enabling AI-powered agents.

About the Author

Jennifer Case writes each month about AI in legal practice, with a focus on solo and small-firm lawyers. She is a lawyer, educator, and AI coach focused on helping solo and small firm attorneys confidently integrate AI into their practice. She offers MCLE-accredited courses, one-on-one coaching, and a bi-monthly AI Mastermind for practicing attorneys. To learn more or work with Jennifer, visit law-tech.ai. Check out her previous column: AI Was Supposed to Democratize Legal Research. What Happened?.

The Two-Track Race

At this year’s flagship conferences, Microsoft Build 2025 and Google I/O 2025, each tech giant unveiled its newest features and laid out a competitive enterprise-level vision for AI.

Here’s a breakdown of each company’s law firm offering:

Microsoft: The Integrated Incumbent

Copilot offers deep integration with popular law tech tools and courtroom e-filing systems, industry-leading compliance, and enterprise-grade security.

And Microsoft continues to innovate. Its newest features from Build 2025 position its platform as an “AI agent factory”:

• Azure AI Foundry Agent Service: A centralized hub hosting 1,900+ models including OpenAI, Meta Llama 3, and xAI Grok 3, enabling law firms and vendors to build tailored, secure agents with enterprise compliance baked in.
• Multi-agent orchestration: Agents can now delegate tasks to each other. Imagine one agent pulling case data, another drafting the motion, and a third scheduling the filing deadline, all working as a team.
• Microsoft Entra Agent ID: A digital identity system that assigns unique IDs to every AI agent, controlling what data they can access and logging all actions for transparency and auditing, critical for legal ethics compliance.
• Copilot Studio enhancements: Low-code tools for building custom agents without developers, now supporting Agent-to-Agent (A2A) communication and Model Context Protocol (MCP) for seamless integration.
• Built-in observability: New dashboards track agent performance, quality, cost, and safety metrics, essential for demonstrating ROI and maintaining client trust.

You must admit it: these features sound incredible. Multiple agents working as a team? Automatic compliance tracking? Built-in ROI metrics? All within Microsoft’s security perimeter? Where do I sign up?

But here’s the catch:

Actually implementing this vision is a massive undertaking. While Copilot offers deep integration with legal tech tools, courtroom e-filing systems, and enterprise-grade security, small firms face significant barriers. Setup requires IT expertise and weeks of configuration.

The $30 per user monthly fee is just the beginning, with unpredictable API costs that grow with every document analyzed and task automated. Most small firms simply lack the resources to effectively deploy and manage such a complex system.

Google: Quietly Building Traction

Google has long been a dominant player in enterprise technology across sectors like education, media, and software. But in legal, it has often been dismissed as too consumer-oriented or lacking in the deep integrations firms require.

Bolstered by recent announcements at I/O 2025, Google is shifting perceptions by:

• Bundled Gemini AI: Eliminating separate licensing fees by including AI and agent building capabilities directly in Workspace plans.
• Embedded AI tools: Gemini now works directly in Gmail, Docs, Sheets, and Meet for summarization, writing, and automation without switching apps.
• Smart document search: Retrieval-Augmented Generation (RAG) allows Gemini to pull relevant information from all your Google Drive and Gmail content.
• Agent Mode: A low-code agent builder within the platform for creating custom AI assistants.
• NotebookLM Plus: Upload 300-page depositions or contracts and get instant summaries, source citations, and audio briefings for review on the go.
• Enhanced Workspace Gems: Custom AI assistants (like ChatGPT’s Custom GPTs) that now access and work with your actual client files, emails, and calendars rather than operating in isolation.
• Workspace Flows: Drag-and-drop automation builder (think Zapier, but native to Google Workspace) that visually connects triggers and actions like “when court email arrives → save attachments to matter folder → create calendar reminder → notify team.”
• Expanded legal tech partnerships: Clio, MyCase, and Billables AI now integrate directly with Gmail and Drive for seamless time tracking, calendaring, and document management without toggling between browser tabs.

Perhaps most importantly for budget-conscious firms, all these features come at a predictable monthly cost with no usage meters or surprise API bills.

But Google faces its own hurdles. While Microsoft has spent years building integrations with legal tech platforms and court e-filing systems, Google’s connections remain limited to a handful of practice management tools. Most legal software vendors prioritize Microsoft compatibility, leaving Google users to rely on clunky workarounds or manual data entry. And despite Google’s enterprise security certifications, the perception challenge remains real: many firms still wonder whether a company built on data collection for advertising can truly safeguard attorney-client communications.

Want an AI Agent? Try These Ideas at the Law Firm:

No matter which platform you use, 2025 is the year of the agents. If that concept still feels foreign, consider the time savings if these digital employees clocked in each day:

Precedent Profiler: Opens new client intake → Scans all past matters for similar fact patterns → Delivers folder with 10 most relevant pleadings, motions, and memos → Highlights what worked/failed → Saves 2 hours of searching through old files.

Calendar Sentinel: Monitors court dockets every morning → Calculates deadlines using local rules → Creates calendar entries with 3-day warnings → Sends alerts when opposing counsel files anything → Eliminates missed deadlines.

Update Drafter: Tracks case milestones (deposition completed, discovery deadline met, settlement offer received) → Generates client update emails with plain English explanations → Includes next steps and timeline → Queues for attorney review → Turns 30-minute task into 2-minute approval.

Discovery Navigator: Receives 500 production documents → Creates master spreadsheet with date, sender, subject, key terms → Flags privileged communications, smoking guns, and inconsistencies → Groups related documents → Saves 3 hours of paralegal review time per production.

Outreach Coordinator: Scans recent case wins and client anniversaries → Drafts LinkedIn posts highlighting success (“Just secured custody modification for client after 2-year battle”) → Creates newsletter content → Schedules social media posts → Builds referral pipeline without extra effort.

Will Legal Industry Tools Become Obsolete?

Not yet. The “no-code” promise of Microsoft and Google still requires:

• Connection the right data sources.
• Configuring permissions and user access.
• Setting up security and compliance safeguards.
• Building reliable workflows with context awareness.
• Maintaining logs and audit trails for ethical and legal reasons.

Until these solutions are made seamless, legal-specific wrappers built atop general-purpose AI (like Claude or GPT) are good alternatives for the less tech-savvy.

Start Where You Are: Try One New Tool This Week

Microsoft is building a powerful infrastructure. Google is betting on ease and accessibility. Both are advancing exponentially with AI agents that can support legal work.

Whether you use Microsoft 365 or Google Workspace, these tools are already available.

Don’t switch platforms. Just activate one AI feature you’re not using yet.

• Microsoft users: Enable Copilot in Outlook to summarize long email threads or use it in Word to draft client letters from bullet points.
• Google users: Turn on Gemini in Gmail for email drafting assistance, or upload a complex PDF to NotebookLM for instant summaries and Q&A.
• Ready for agents? Create a simple automation in Power Automate (Microsoft) or Workspace Flows (Google) to auto-file emails by client name or send calendar reminders for deadlines.

Test with real work: Pick one task that takes 30+ minutes daily. Time how long the AI version takes and how much editing you need.

The goal: Find one tool that saves 15 minutes per day. That’s 60+ hours per year—worth more than the subscription cost.

AI agents are not part of some distant future tech to investigate someday. They’re active teammates awaiting deployment at your command. Start where impact matters most and build with purpose.