AI isn’t changing the game—it’s exposing how you think. In this episode, I sit down with Misty Shafer Sterne, Vice President of Commercial Technology at American Airlines, to explore what it really takes to lead with AI inside a complex, high-stakes organization. We go beyond the usual productivity narrative and dig into something far more powerful: how AI can sharpen decision-making, surface better questions, and help leaders operate with greater clarity and intent.

Misty shares her journey from chasing efficiency to building a personal system for thinking—using AI as a partner to capture ideas, pressure test decisions, and improve how she shows up as a leader. We also unpack why experimentation matters more than metrics early on, how to avoid automating broken processes, and what it looks like to lead in the open so teams can follow. This is a conversation about performance, not productivity—and what it means to truly unlearn how we work.

Key Takeaways

AI amplifies how you think: The real advantage isn’t speed but improving clarity, judgment, and decision-making quality.
Productivity is just the entry point: The biggest gains come from using AI to enhance performance, not just efficiency.
Experimentation must come before measurement: Over-indexing on productivity metrics too early can shut down innovation.
Leaders must unlearn being the “answer person”: Great leadership shifts toward asking better questions rather than having all the answers.
Decision velocity matters more than idea volume: Success comes from quickly identifying which ideas are worth pursuing, not generating more ideas.

Additional Insights

AI as a thinking partner: Misty’s breakthrough came when she used AI to pressure test ideas instead of manage tasks.
Externalizing thinking creates clarity: Capturing raw, messy thoughts helps reveal patterns and improve decision-making.
Your thinking becomes a reusable asset: AI enables leaders to build a system that stores and evolves their ideas over time.
Automating bad processes makes them worse: AI should be used to redesign workflows, not just accelerate existing inefficiencies.
Leadership requires learning in public: Vulnerability and visible experimentation help drive adoption across teams.

Episode Highlights

00:00 – Episode Recap

A shift from chasing productivity to unlocking better thinking transforms how leaders use AI—turning it into a true decision-making partner rather than just a tool.

02:00 – Guest Introduction: Misty Shafer Sterne

Barry introduces Misty, VP of Commercial at American Airlines, leading AI-driven decision-making across pricing, customer experience, and revenue.

04:25 – From Perfection to Curiosity

Misty reflects on her journey from needing all the answers to embracing vulnerability and asking better questions as a leader.

07:45 – The Productivity Trap

Early AI use focused on inbox management and efficiency, but Misty realized this wasn’t where real value lies.

09:30 – AI as a Thinking Partner

Using AI to externalize thoughts, identify patterns, and pressure test ideas unlocks a new level of clarity and decision-making.

12:30 – Performance Over Productivity

The real benefit of AI is improving how leaders show up, think, and collaborate—not just getting more done.

15:15 – Capturing Ideas Before They’re Lost

Verbal processing and real-time capture help preserve insights and connect ideas over time.

18:18 – Building a System of Thinking

Accumulating ideas creates a long-term asset that helps leaders identify patterns and improve decisions.

21:25 – Why Experimentation Needs Space

Over-measuring productivity too early can limit exploration and reduce the potential of AI adoption.

24:33 – Context Matters in Decisions

Capturing why decisions were made enables better future judgment as conditions change.

29:04 – Leading by Example

Misty shares how modeling experimentation helped shift her organization from fear to adoption.

33:40 – The Danger of Automating Bad Processes

AI can amplify poor systems—leaders must rethink workflows, not just speed them up.

36:03 – Redesigning Work for Better Outcomes

True transformation comes from changing behavior and systems, not just adopting tools.

38:45 – Unlocking Ideas Across the Organization

AI democratizes innovation, requiring leaders to step back and let the best ideas emerge from anywhere.

FAQs

1. What is the biggest mistake leaders make when adopting AI?

Focusing too much on productivity metrics early on instead of creating space for experimentation and learning.

2. How should leaders actually use AI in their daily work?

As a thinking partner—to capture ideas, pressure test decisions, and improve clarity, not just automate tasks.

3. What does “decision velocity” mean?

It’s the ability to make faster, higher-quality decisions with confidence by using better information and structured thinking.

4. Why is experimentation so important in AI adoption?

Because the real value emerges through exploration—rigid expectations can limit discovery and innovation.

5. How can leaders avoid damaging their teams when introducing AI?

By leading with transparency, modeling behavior, and ensuring AI enhances collaboration rather than creating pressure or fear.

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