Winston Weinberg, CEO and cofounder of Harvey AI, a legal tech startup disrupting Big Law, shared insights about the future of the legal profession during a recent Reddit Ask Me Anything session. Despite his company’s rapid success in bringing artificial intelligence to the legal industry, Weinberg maintains that the core skills that define exceptional lawyers will remain unchanged in the AI era.
According to Weinberg, the best legal partners Harvey collaborates with excel at understanding business needs and framing agreements accordingly. “I’ve found that the best partners are the ones that are incredible at understanding what the actual business needs are and framing an agreement based on that,” he explained. In litigation, success comes from developing compelling arguments and narratives rather than manually reviewing discovery documents—tasks increasingly handled by AI.
Weinberg emphasized that junior lawyers should prioritize gaining client experience as early as possible in their careers. He advocates for firm leaders to provide more client-facing opportunities to junior associates, even if it means accepting some mistakes along the way. “That’s actually the main thing I pitch to firm leaders - they should focus more on giving juniors client experience, and be okay with them making some mistakes - that’s how they become the best partners in the future,” he wrote.
Harvey recently achieved an $8 billion valuation following a funding round led by prominent venture capital firm A16z, cementing its position as a major player in legal AI. Despite this success, Weinberg maintains a realistic view of the competitive landscape, stating that no single company—including Harvey—will dominate the entire legal tech market. “I don’t think a single player is going to capture all of the pretty enormous amount of value that will be created in the next 10 years in this space,” he noted.
For lawyers considering a transition into the tech startup world, Weinberg offers candid advice: develop resilience and tolerance for failure. “Junior lawyers are often practiced perfectionists, and startups are all about risk, reward, and resilience,” he told Business Insider. This mindset shift represents a significant departure from traditional legal training, which typically emphasizes precision and risk avoidance over experimentation and iteration.
Key Quotes
So I actually think a lot of what makes an incredible lawyer today is still what will make one tomorrow.
Winston Weinberg, Harvey’s CEO, made this statement during his Reddit AMA, emphasizing that despite AI’s disruption of legal work, fundamental lawyering skills around business understanding and strategic thinking will remain essential.
I’ve found that the best partners are the ones that are incredible at understanding what the actual business needs are and framing an agreement based on that.
Weinberg highlighted that the most successful lawyers Harvey works with focus on strategic business understanding rather than technical document work—tasks increasingly automated by AI systems.
Junior lawyers are often practiced perfectionists, and startups are all about risk, reward, and resilience.
In advice to lawyers interested in tech careers, Weinberg identified a cultural gap between traditional legal training and startup environments, emphasizing the need to embrace failure as part of innovation.
I don’t think a single player is going to capture all of the pretty enormous amount of value that will be created in the next 10 years in this space.
Despite Harvey’s $8 billion valuation, Weinberg acknowledged that the legal AI market is large enough to support multiple successful companies, suggesting significant growth opportunities across the sector.
Our Take
Weinberg’s perspective represents a mature view of AI’s role in professional services that contrasts with both extreme optimism and fear. His emphasis on unchanged core competencies suggests that AI serves as an augmentation tool rather than replacement, handling commoditized tasks while elevating the importance of uniquely human skills like relationship-building and strategic judgment. The $8 billion valuation validates this approach, indicating that investors see legal AI as enhancing rather than eliminating the profession. However, Weinberg’s advice about client experience raises questions about how firms will restructure when junior associates no longer spend years on document review. This transition period could be challenging for traditional law firm economics and partnership tracks. The acknowledgment that no single player will dominate also suggests we’re still in the early stages of legal AI, with significant innovation and competition ahead.
Why This Matters
This perspective from Harvey’s CEO is significant because it addresses a critical question facing the legal profession: how will AI fundamentally change what lawyers do? While many fear AI will replace legal jobs, Weinberg’s insights suggest a more nuanced reality where AI handles routine tasks while human judgment remains paramount. Harvey’s $8 billion valuation demonstrates that investors believe legal AI represents a massive market opportunity, potentially transforming how law firms operate and deliver services to clients.
The emphasis on client relationships and strategic thinking over document review signals how AI is reshaping junior lawyer development. Traditionally, associates spent years on tedious tasks like discovery review to build expertise. With AI handling these functions, law firms must reimagine training programs to focus on client interaction and strategic skills earlier in careers. This shift could democratize access to meaningful legal work while potentially reducing the time needed to develop senior-level capabilities. For the broader legal industry, Harvey’s success and Weinberg’s philosophy suggest that AI adoption will accelerate, creating pressure on firms to adapt or risk losing competitive advantage to more tech-savvy competitors.
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Source: https://www.businessinsider.com/harvey-ceo-advice-young-lawyers-2025-12