The Challenges Facing In-House Legal Teams
CCBJ: In your tech talk, you mentioned that 71 percent of in-house lawyers are considering leaving their roles. What are the key factors driving this dissatisfaction, and how have successful companies improved retention?
Mike Tobias: The challenges facing in-house legal teams are multifaceted. High workload, constant urgency, and a lack of understanding about the unique role lawyers play within an organization contribute significantly to burnout. In-house counsel must balance being both risk guardians and commercial enablers—a dual responsibility that is often misunderstood.
Moreover, their personality profile and work output differ from other departments, yet they are expected to function within rigid corporate structures. These misalignments create what we call a “doom loop,” where conscientious, high-performing lawyers respond to pressure by working harder. Over time, this unsustainable cycle leads them to burnout and, ultimately, departure.
Companies that successfully improve retention recognize these structural issues and address them through better workflow management, clearer role definitions, and legal technology that genuinely alleviates workload rather than adding to it.
Why Legal Tech Often Fails
With 77 percent of legal tech projects failing, what common mistakes do companies make, and can you share an example of a company that successfully avoided these pitfalls?
The most common mistake is viewing legal tech selection through a traditional IT procurement lens—focusing on feature checklists rather than business outcomes.
In-house legal is distinct in its needs, yet many companies allow IT to lead the selection process without fully understanding how legal teams operate. Over the past few years, we’ve seen legal tech spending nearly double, yet burnout has worsened. That tells us that more technology isn’t the solution—it must be the right technology, implemented correctly.
Another major issue is failing to anticipate change. Businesses constantly evolve—new regulations, management shifts, market fluctuations—and legal tech must be adaptable. The most successful companies take a future-proofing approach, where before commencing a project, they conduct a “pre-mortem.” In this process, they imagine what could go wrong with the project and then work backward to plan ways to avoid potential pitfalls. This proactive mindset helps prevent costly missteps.
So, going into any technology selection process requires you have shared agreement on what business outcomes you are trying to bring about, and what changes to the business you need to be able to easily accommodate.
Adapting to the Future of In-House Legal
As we move into 2025, what major shifts do you see impacting in-house legal teams, and how are they preparing for these changes?
AI is the dominant conversation in legal tech today. While there’s excitement and anxiety about its implications, the reality is that foundational challenges remain—retention, workload, and operational inefficiencies. Until these core issues are addressed, AI alone won’t be a silver bullet.
However, high-performing legal teams are focusing on first principles: streamlining workflows, reducing redundant manual tasks, and ensuring their teams are positioned to thrive. The companies that get ahead will be those that integrate AI thoughtfully—augmenting legal teams rather than overwhelming them with another layer of complexity.
The Disconnect Between Legal and Technology
What operational or technological challenges do companies commonly face when they come to you for guidance? A recurring theme is the realization that document management systems (DMS) alone don’t solve operational inefficiencies. While they help with storage, searchability, and security, they don’t address operational effectiveness—who is responsible for what, what’s pending, what’s high priority, etc.
Many legal teams come to us after implementing a DMS, expecting it to solve their workflow issues, only to find that it doesn’t. We help them transition to structured processes, focusing on areas of high impact like contract and matter management. By starting with their biggest pain points, they can progressively enhance their operations rather than trying to overhaul everything at once.
AI’s Role in Legal Operations
Where is AI currently delivering the most value for in-house legal teams, and what misconceptions still exist?
Right now, AI is proving most effective in document-intensive tasks—summarization, drafting,
and review. However, one of the biggest challenges is adoption speed. AI evolves at a rapid
pace, but individuals, organizations, and particularly legal teams adopt it at a much slower rate.
And regulations—that change at a much slower pace than technology and the demands of business—are likely to further impede the adoption and integration of AI into legal work.