From Curiosity to Competence: A GC’s Journey to Becoming AI-Savvy

For many General Counsels, the journey toward becoming AI-savvy does not begin with technology; it begins with curiosity. Questions like “Where can AI actually help?” or “What does this mean for my team?” often come long before any tool adoption. Yet today’s legal leaders are increasingly expected to move beyond curiosity and develop real competence in how artificial intelligence shapes contract workflows, risk management, and business strategy.

The shift is happening quickly. Gartner research shows that 36% of General Counsels are already prioritizing AI adoption and capability-building within their legal departments, reflecting a growing recognition that AI literacy is becoming a core leadership skill. At the same time, broader industry data indicate that 88% of organizations now use AI in at least one business function, creating pressure on legal teams to match the digital maturity of the rest of the business. 

This evolution is changing how GCs lead. Instead of focusing solely on legal expertise, they are increasingly responsible for shaping digital agreement strategies, guiding contract lifecycle management workflows, and helping teams navigate AI responsibly. Becoming AI-savvy is not about learning to code or replacing legal judgment with automation. It is about developing the confidence to evaluate new tools, redesign processes, and build teams that can adapt to a rapidly changing landscape.

The path from curiosity to competence is rarely linear. But for today’s GC, it is becoming an essential part of the role and a defining factor in the future of legal leadership.

Key Takeaways

• Becoming AI-savvy starts with curiosity but requires experimentation, learning, and leadership evolution.

• Modern General Counsels must combine legal expertise with workflow thinking, governance awareness, and data-driven decision-making.

• AI competence is less about technical skills and more about strategic thinking and guiding teams through change.

• Structured experimentation helps legal leaders understand where AI adds value without increasing risk.

• Strong governance and change management are essential for sustainable AI adoption.

• The future GC role blends legal judgment with operational and technological awareness.

Why AI Literacy Matters for Today’s GC

AI is not just another technology trend. It is changing how companies work, how deals move forward, and how legal teams deliver value. For General Counsels, understanding AI is becoming less optional and more essential.

Legal departments are under pressure to move faster while managing increasing risk. Contract volumes are growing. Negotiations are becoming more complex. Digital agreements are replacing traditional workflows. Business teams expect legal to keep pace with automation happening across sales, finance, and operations.

AI helps address these challenges by improving efficiency and visibility. Tools can summarize contracts, highlight risks, and support faster decision-making. But technology alone is not the solution. The real shift comes when legal leaders understand how to use AI strategically.

For many GCs, the starting point is mindset. Becoming AI-savvy does not mean becoming technical experts. It means learning to ask better questions:

• Where does legal spend the most time?
• Which workflows slow down deals?
• What tasks can be standardized or automated?

This shift reflects a broader evolution in the GC role. Today’s legal leaders are not only advisors. They are operators who help design processes, evaluate technology, and guide teams through change.

AI literacy also strengthens collaboration with the business. Sales teams want faster approvals. Product teams need guidance on data and risk. Executives expect legal to provide strategic insights supported by data. Understanding AI enables GCs to participate in these conversations with confidence.

In many ways, AI literacy is becoming a core leadership capability. It helps GCs move from reacting to requests toward shaping how work happens across the organization.

Understanding why AI matters is only the starting point. The real transformation happens as GCs move through distinct stages of adoption.

Stage 1: Curiosity — The Starting Point for AI Adoption

For most General Counsels, the path toward becoming AI-savvy does not begin with a formal strategy. It begins with curiosity.

Curiosity often shows up in small ways. A GC might explore how AI summarizes contracts. They may ask how other teams use AI tools or attend internal demos to understand what is possible. These early steps help shift the mindset from uncertainty to exploration.

At this stage, the goal is not mastery. It is awareness.

Many legal leaders hesitate because AI feels technical or unfamiliar. There are concerns about accuracy, risk, and loss of control. These concerns are valid. However, curiosity helps legal leaders move past hesitation and start learning through observation and experimentation.

Curiosity also changes how GCs approach their role. Instead of asking whether AI will replace legal work, they begin asking how AI can support better decision-making.

Andrew Epstein, General Counsel of Demandbase, describes this mindset as moving beyond traditional boundaries:

I’ve always liked to color outside the lines a little bit… I wanted to have the opportunity to impact a business beyond just legal.

This approach reflects a key shift. AI adoption is not about becoming a technologist. It is about expanding the scope of legal leadership. GCs who lean into curiosity are more likely to identify opportunities where AI improves workflows without compromising risk management.

Practical examples of curiosity-driven exploration include:

• Testing AI summaries for long contracts or policies.
• Asking vendors how AI supports contract lifecycle management.
• Observing how business teams use AI tools in daily work.
• Encouraging team members to share experiments or lessons learned.

Curiosity creates momentum. It lowers the barrier to learning and helps legal teams engage with AI in a safe and controlled way. Over time, this curiosity becomes the foundation for deeper experimentation and skill-building.

Stage 2: Experimentation — Building Practical Understanding

Once curiosity takes hold, the next step is experimentation. This is where General Counsels begin turning ideas into practical experience. Instead of only learning about AI, they start testing how it fits into real legal workflows.

Experimentation does not require large investments or complex implementations. In many cases, it begins with small, controlled use cases:

• Using AI tools to summarize digital agreements.
• Testing clause comparison or redlining features.
• Drafting internal memos or first drafts with AI assistance.
• Exploring how AI supports contract lifecycle management tasks.

These early experiments help legal leaders understand both the strengths and limits of AI. They also build confidence. GCs learn where automation speeds up work and where human judgment remains critical.

One common mistake during this stage is focusing too much on new tools instead of real problems. Effective experimentation starts with workflow challenges, not technology hype.

As Andrew Epstein explains:

It’s less about what new shiny tool you sign up for, and more about how you give your team permission to use the tools you already have.

This insight highlights an important shift. AI adoption is not only about purchasing software. It is about creating a culture where teams feel encouraged to explore new ways of working.

Experimentation also helps legal teams build internal knowledge. Team members learn how to write better prompts, evaluate AI outputs, and understand risk boundaries. These skills gradually turn curiosity into practical capability.

For many GCs, experimentation becomes a leadership exercise. They set expectations that learning is allowed. They create space for testing. And they show that innovation can happen without sacrificing legal standards.

Stage 3: Competence — Becoming an AI-Savvy Legal Leader

Competence begins when AI moves from experimentation into everyday decision-making. At this stage, General Counsels are no longer just testing tools. They are shaping how AI supports legal strategy and team operations.

Being AI-savvy does not mean mastering technology details. It means understanding how AI fits into the legal function. Competent legal leaders know where automation adds value and where human expertise remains essential.

This stage often includes several shifts:

• Moving from individual experimentation to team-wide workflows.
• Establishing governance and risk guardrails.
• Aligning AI initiatives with business priorities.
• Evaluating vendors and tools with a strategic lens.

Competence also requires self-awareness. Many GCs step into unfamiliar territory when working with AI. Learning to acknowledge gaps and seek support becomes a key leadership skill.

Andrew Epstein highlights this shift in mindset clearly:

You have to be honest with yourself around areas where you don’t have experience and ask who can help you grow that experience.

This perspective reflects the transition from curiosity to confidence. Instead of trying to know everything, effective leaders focus on building strong networks, learning from peers, and creating collaborative environments.

At this stage, AI adoption becomes less about efficiency alone and more about long-term impact. GCs begin thinking about how digital agreements generate data, how contract lifecycle management can improve visibility, and how AI insights support strategic decisions.

For a deeper look at how AI is reshaping contract workflows, explore this guide to AI in contract management.

Ultimately, competence is not a final destination. It is an ongoing process. AI continues to evolve, and legal leaders must continue learning, adapting, and guiding their teams through change.

Key AI Skills Every GC Needs in 2026

As artificial intelligence becomes more embedded in legal work, the role of the General Counsel continues to evolve. Becoming AI-savvy is less about technical expertise and more about developing practical leadership capabilities that help legal teams adapt, make informed decisions, and operate effectively in a technology-driven environment.

Strategic Thinking About Workflows

AI delivers the most value when applied to structured processes. General Counsels need to understand how work flows across drafting, negotiation, and execution rather than viewing tasks in isolation. A workflow-first perspective helps leaders identify where AI can support efficiency without disrupting legal oversight.

Prompt Literacy and Structured Communication

Modern AI tools rely on clear instructions. Legal leaders benefit from learning how to provide context, refine outputs, and evaluate results critically. This skill enables teams to use AI responsibly while maintaining professional judgment.

For practical examples, see this guide to LLM prompting for lawyers.

Risk and Governance Awareness

AI introduces new considerations around data use, confidentiality, and accuracy. GCs must establish clear guardrails that allow experimentation while maintaining compliance and accountability. Strong governance ensures that AI supports decision-making rather than replacing it.

Data Awareness and Analytical Thinking

Digital agreements increasingly generate actionable data. Understanding how to interpret trends, identify recurring risk areas, and connect contract insights to business outcomes allows legal leaders to contribute more strategically.

Change Management and Team Leadership

AI adoption depends on people as much as technology. Successful GCs encourage learning, create space for experimentation, and help teams build confidence gradually. Leadership at this stage focuses on guiding behavior change rather than mastering tools.

Common Mistakes GCs Make When Starting with AI

Understanding common mistakes can help legal leaders avoid unnecessary setbacks and focus on building sustainable capabilities.

Common challenges include:

• Starting with tools instead of problems

AI adoption works best when it addresses real workflow challenges. When organizations select technology before understanding their contract lifecycle management processes, adoption often stalls. Clear goals and defined use cases lead to better outcomes.

• Expecting immediate transformation

AI improves efficiency over time, but it does not replace structured workflows or human judgment overnight. Early experiments should focus on learning and iteration rather than instant results.

• Underestimating change management

Technology alone does not change behavior. Lawyers may feel uncertain about AI or worry about risk. Leaders who create safe environments for experimentation help teams build confidence gradually.

• Lack of governance and clear guardrails

Without guidelines around data usage, confidentiality, and review processes, teams may hesitate to use AI tools. Strong governance enables innovation while maintaining compliance.

• Trying to learn everything alone

AI adoption works best as a collaborative effort. Partnering with legal operations, IT teams, and external experts allows GCs to focus on strategy instead of technical complexity.

Avoiding these pitfalls does not require perfection. It requires clarity, patience, and a willingness to evolve alongside technology. When legal leaders approach AI as a long-term journey, they create stronger foundations for sustainable change.

The Future GC: AI-Savvy, Data-Aware, and Strategically Positioned

The role of the General Counsel is changing quickly. AI is not only introducing new tools but reshaping expectations around leadership, decision-making, and business impact. The future GC is no longer defined only by legal expertise. Success increasingly depends on the ability to combine legal judgment with operational awareness and technological confidence.

As AI becomes part of everyday workflows, legal leaders are expected to guide how digital agreements are created, negotiated, and managed. This means understanding how contract lifecycle management connects with broader business processes. GCs who develop this perspective can influence strategy earlier and help organizations move faster without increasing risk.

Data awareness will also play a central role. AI turns contracts into sources of insight. Patterns around negotiation timelines, risk exposure, and performance metrics become visible in ways that were not possible before. Legal leaders who understand how to interpret this data can contribute more meaningfully to executive discussions and long-term planning.

At the same time, the human element of legal leadership remains essential. AI supports analysis and efficiency, but judgment, negotiation skills, and ethical oversight remain core responsibilities. The most effective GCs will learn how to combine human expertise with AI-supported insights rather than treating them as competing forces.

One perspective that captures this balance is the recognition that AI creates opportunity rather than replacement:

Lawyers who leverage AI are going to be massively advantaged — but it doesn’t mean all the jobs go away.

This reflects the broader reality of legal transformation. The future is not about replacing lawyers with technology. It is about enabling legal professionals to work at a higher level of impact.

As organizations continue to adopt AI across departments, GCs who build competence early will be better positioned to lead change. They will shape how AI supports contract management, guide ethical use of technology, and ensure that legal remains a strategic partner in business growth.

Conclusion

Becoming AI-savvy is not a single milestone. It is an ongoing journey that starts with curiosity, grows through experimentation, and evolves into confident leadership. As AI reshapes how digital agreements and contract lifecycle management work, General Counsels have an opportunity to move beyond operational tasks and play a more strategic role in driving business outcomes.

The goal is not to replace legal expertise with technology, but to enhance it. GCs who build the right skills today will be better prepared to guide teams, manage risk, and unlock new value from AI-driven workflows.

If your organization is exploring how AI can support smarter contract management and more efficient legal processes, now is the right time to evaluate how structured platforms and workflows can help turn curiosity into lasting competence.

FAQs

1. What AI skills do General Counsels need in 2026?

Ans: General Counsels need strategic workflow thinking, prompt literacy, risk governance awareness, data interpretation skills, and strong change management capabilities. The focus is on leadership and decision-making rather than technical expertise.

2. How can GCs use AI to become more strategic?

Ans: AI reduces time spent on repetitive work and provides better visibility into contracts and risks. This allows GCs to focus on high-value tasks such as negotiation strategy, business alignment, and proactive risk management.

3. What courses or learning paths can help lawyers understand AI technology?

Ans: Lawyers can start with introductory AI courses focused on legal applications, contract lifecycle management, and AI governance. Practical workshops, vendor training sessions, and peer learning communities often provide the most relevant hands-on experience.

4. How is AI changing the role of the General Counsel?

Ans: AI is expanding the GC role from legal advisor to strategic operator. Legal leaders are increasingly expected to guide technology adoption, design efficient workflows, and use data insights to support business decisions while maintaining strong risk oversight.