Mindfulness Meets AI: 5 Lessons from Leslie Witt on Building Empathetic Digital Wellbeing Tools
Welcome to the latest issue of the AI Community Learning Series – a space to explore how leaders and innovators are reshaping industries with AI 🚀. In this session, Leslie Witt, former Chief Product and Design Officer at Headspace, shared how she and her team built Ebb, an empathetic AI companion designed to support mental wellbeing. If you missed it, here are the highlights of our conversation. Watch the replay here.
“We weren’t just building fast — we were building with care.”
In an industry that often celebrates speed, Leslie Witt reminded us that some things are too important to rush. Developing AI tools for mental health, like Ebb, demanded more than shipping quickly. It required intentionality, clinical rigor, and ethical oversight.
1. Design for the Gaps Between Human Care
Leslie described Ebb not as a replacement for therapists or coaches, but as a companion that fills the in-between moments— those late nights, lonely hours, or transitional spaces where human care isn’t always available.
“One user shared that Ebb became a source of support between therapy sessions — something they hadn’t even realized they needed.”
By targeting reflection and emotional journaling, Ebb helps users feel seen and supported while guiding them to Headspace’s vast content library through clinically-informed AI prompts.
2. Ethical AI Isn’t a Statement — It’s a Daily Practice
Headspace didn’t just write down principles for ethical AI — they operationalized them. From red-teaming to testing for bias and hallucinations, the team created a “small but mighty” framework grounded in clinical standards.
“There’s no shortcut to testing and no end to oversight.”
Ebb’s AI is built using motivational interviewing techniques and includes clear boundaries: it doesn’t give advice, but it does empathize, reflect, and route users to the right support — including escalation paths for those in crisis.
3. Hyper-Personalization is the New Onboarding
Many users come to Headspace without knowing what they need — whether it’s better sleep, stress relief, or a deeper mindfulness practice. Leslie emphasized how traditional pathways like “search” or “browse” often fall short.
“Ebb meets people where they are, not where we expect them to be.”
By using conversational prompts, the AI discerns a user’s emotional state and context, then makes personalized, explainable content recommendations — creating a path to mindfulness that feels intuitive and relevant.
4. Feedback Is a Clinical Tool
Data wasn’t just about engagement. The team measured whether Ebb was actually helping people feel less anxious, less depressed, and more rested. They tracked clinical metrics alongside behavior patterns — and made space for stories.
“Our average session length was far longer than we imagined. That told us users were really opening up.”
From thumbs-up/down responses to end-of-session surveys and anonymized conversation audits, feedback became a continuous loop of insight — not a checkbox.
5. AI Can Help Tackle the Loneliness Epidemic — But It Must Be Handled with Care
Leslie is optimistic about AI’s potential to help address the global crisis of loneliness — especially among younger generations and underserved communities. But she also cautioned against reckless deployment.
“Tech is invisible — but its harm can be just as real and deadly as physical failure. We need to treat AI in mental health with the same care we’d give a building’s structural safety.”
Her call to action? Slow down, build responsibly, and commit to industry-wide ethical standards before the damage is done.
Final Reflection: “Exhale. Life Happens Over Time.”
As we wrapped up, Leslie offered advice to rising leaders navigating their own wellbeing and careers.
“Be a lifelong learner. Follow your gut. And if something feels unhealthy — you’re probably right.”
Whether you’re building with AI, managing burnout, or figuring out your next move, Leslie’s wisdom is a reminder: empathy starts with how we build — and how we treat ourselves.
From AI-based learning programs to connecting with like-minded enthusiasts from leading tech companies, the AI Enthusiast Community is your space to exchange ideas, explore tools, and shape the future of AI together. And trust us, this is just the beginning—stay tuned for what’s next!
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