How do you lead through AI-driven change when the map hasn’t been drawn yet?

Anna Gressel, partner and global co-head of AI at Freshfields, has built a career exploring questions without established answers, from neuroscience to some of the hardest legal, safety, governance, and strategy questions in AI.

In this conversation, Anna and Gabrielle explore what it takes to move into unfamiliar territory with curiosity, creativity, and sound judgment.

For Anna, the fact that something is new isn’t a reason to avoid it. It can be the reason to explore. That mindset shapes how she approaches novel problems: turning the prism, connecting ideas across disciplines, asking what might still be missing, and “scaffolding forward” toward challenges that haven’t fully arrived yet.

But exploration isn’t the opposite of rigor. Anna works on high-stakes AI matters where safety, compliance, liability, and judgment matter enormously. The joy comes from helping clients solve hard problems, create responsibly, and find a wise path forward.

The conversation also moves from individual AI fluency to organizational strategy. AI often doesn’t create entirely new organizational problems; it throws existing questions into sharper relief. What should we preserve? What needs to change? What is our competitive edge? Are we adopting AI because it serves a strategic goal, or simply for adoption’s sake?

The goal isn’t predicting exactly where AI will be in five years. It’s building capabilities now that create more options later.

In This Episode

• Why unexplored territory can be an invitation rather than a warning
• Turning the prism: connecting ideas across disciplines
• Building AI fluency through experimentation and peer learning
• Why even AI experts still feel behind
• Holding joy, creativity, risk, and judgment at the same time
• Why AI can surface organizational challenges that already existed
• Strategic AI adoption vs. adoption for adoption’s sake
• Building capabilities now to create future optionality
• Unlearning the comfort of familiar patterns

Your Rep: Challenge the Familiar

Think of one thing you hate doing or one familiar process you rarely question.

Ask AI to interview you about how it works today, where the pain points are, and what might be removed, simplified, or done differently.

Then ask: What could I stop doing? What could AI help me automate? What would I redesign if I were starting from scratch?

You don’t have to automate everything. The rep is to challenge the comfort of the pattern and explore what might be possible.

Chapter Markers

02:32 Everyday AI joy: spreadsheets as a thought partner
04:15 Why unexplored territory is worth pursuing
11:00 Turning the prism across disciplines
17:05 Building AI fluency through exploration
22:05 Why even experts feel behind
26:00 Joy, risk, and sound judgment
33:15 How AI surfaces existing organizational challenges
35:35 Why AI adoption needs a strategy
38:15 Building capabilities for an uncertain future
39:25 Unlearning the comfort of the pattern
42:20 Your Rep: challenge a familiar way of working
43:30 What makes the future of AI exciting

Sources & Resources

• Anna Gressel, The AI Drop (https://www.freshfields.com/en/our-thinking/podcasts/the-ai-drop)
• ABA Commission on Women in the Profession + ABA Center for Innovation, 21 Days of AI: A Grit and Growth Mindset Challenge (https://www.americanbar.org/groups/diversity/women/initiatives_awards/grit-project/ai-grit-challenge-home/)
• Sebastian Seung / EyeWire, connectomics and brain-mapping research

Ways to Connect with Gabrielle

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GK Strategic Advisory: gkstrategic.com
LinkedIn: linkedin.com/in/gabrielle-kohlmeier