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• AI x Human Leadership for Navigating Complexity

  • Start
    06/10/2026
  •  
  • End
    06/24/2026
  •  
  • Schedule
    3 sessions
  • Location
    Canopy, Menlo Park
  • Spaces left
    13

  Register

  

  AI × Human Leadership - A 3-session experiential lab for women leaders ready to stop waiting for the perfect moment  and start moving

  The leaders who thrive in uncertainty aren't the ones with the best strategy.
  They're the ones who stopped waiting for the perfect moment to act.
  Most high-performing women we know have the intelligence, the experience, and the insight. What gets in the way isn't capability.

  Join us to experience how the shift happens

  • Dates /Times:  June 10, June 17, June 24 | 5:00 -6:30 PM PT
  • Location: Canopy, Menlo Park

  Session 1: Unlocking Your Inner Experimenter June 10 at 5pm

  Most leaders facing complexity don't have a strategy problem. They have a fear response and it's completely rational. This session interrupts it. Through live micro-experiments, you'll discover why the instinct to protect and perfect is actually slowing you down and experience firsthand what becomes possible when you give yourself permission to try instead of waiting until you're sure.

  You'll leave with:

  • Your specific "gremlin" pattern named and defanged  the internal voice that surfaces whenever change, AI, or bold action is required

  • One small, real experiment to run before Session 2, tied to a challenge right now

  • A visceral  understanding of why experimentation is the fastest path through complexity

  Session 2: The Good Enough Start June 17 at 5:00 PM

  Perfectionism isn't about high standards. It's about waiting;  and waiting is a strategy for staying stuck.We open by debriefing the experiments you ran between sessions. Every outcome is treated as data, not judged as success or failure. Then we go deeper on what makes it so hard to start before you're ready, and what actually happens when you do.

  You'll leave with:

  • Real data about your own leadership patterns, drawn from your own experiment

  • A concrete protocol for giving yourself and your teams permission to start 

  • The Learning Autopsy: a simple framework for extracting insight from anything that didn't go as planned

  Session 3: The Agile Leader June 24 at 5:00 PM

  The goal was never to be right. The goal is to learn faster than the world is changing. This closing session integrates everything from the lab and sends you home with practices built to last not just intentions that fade when Monday hits.

  You'll leave with:

  • A personalized experimentation practice specific enough to actually do, anchored real challenges

  • A 30-day plan you'll start before you leave the room

  • A learning partner and a clear picture of how to extend this practice to the teams you lead

  Reserve your seat today (14 spots total, this fills fast) 

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• Second Act! You’re Not Lost, You’re Outgrowing Your Life

  • When
    06/25/2026
  •  
    5:00 PM - 6:00 PM
  • Location
    Zoom

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  You’re Not Lost, You’re Outgrowing Your Life

  A session for women who've arrived and are ready for more.

  There is a particular kind of restlessness that visits high-achieving women in midcareer. The title is there. The track record is solid. The respect is real. And yet, something quietly insists that there is more. Different. Truer.

  That feeling is not a warning sign. It is a compass.

  Executive coach Colleen Pimentel reframes midlife career restlessness not as a crisis to manage, but as a signal to follow. In this session, she will guide you through a practical framework designed for senior women who are ready to move from confusion to clarity, and from restlessness to reinvention.

  This session is not about walking away from what you have built. It is about building forward from who you are becoming.

  WHAT YOU WILL TAKE AWAY

  1. Clarity over confusion: Understand why the traditional linear career path may no longer fit, and how to name what you actually want next.
  2. Fear reframed as growth: Learn to recognize dissatisfaction as a signal of expansion and build courage without making reckless leaps.
  3. A framework you can use: Leave with a grounded model for sustainable reinvention that honors where you are and where you are going.

  ABOUT THE SPEAKER 

  With a 30-year legacy in Big Tech  (Google, Oracle, etc.) and over 10 career reinventions, Colleen doesn't just understand the climb, she knows how to find your true purpose and master the art of evolving to live it. 

  She is now a dedicated speaker, author and trusted mentor focused on guiding high-achieving individuals toward their next chapter. Colleen shares proven, practical strategies to gain crystal-clear vision, ensure value alignment, and take bold, intentional action. She empowers groups and individuals to move past exhaustion and build a career defined not just by achievement, but by deep, unwavering purpose.

  THIS SESSION IS DESIGNED FOR YOU IF you are a senior woman leader navigating one or more of the following:

  • A career transition or role change you have been quietly considering
  • Leadership fatigue that is not solved by a vacation or a promotion
  • A desire for more aligned impact, but no clear path yet to get there

  Reserve your seat today!

  
  

  
  

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• Public Speaking: Building Confidence, Authenticity, and Engagement

  • When
    07/15/2026
  •  
    4:00 PM - 5:00 PM
  • Location
    Zoom

  Register

  
  

  Speak with confidence. Lead with presence.

  
  

  Most leaders are never taught how to speak, they are just expected to. This is a practical, judgment-free session for senior women who want to own the room, not just survive it.

  
  

  Whether you are addressing your board, pitching a new idea, leading a town hall, or simply trying to feel more at ease in the rooms you already belong in, the ability to communicate with confidence changes everything.

  The goal is not to be perfect. It is to be present, clear, and unmistakably you.

  In this hands-on session, executive coach and product leadership veteran Diana Stepner shares the practical techniques she has used and taught across startups, enterprise organizations, and executive coaching engagements. You will leave with tools you can use immediately, in your next meeting, your next presentation, your next conversation that matters.

  • Event Date / Time: July 15 | 4:00 - 5:00  PM PST 
  • Location: Zoom

  What you will take away

  1. Confidence that is yours: Unlock your speaking potential and learn to channel nervous energy as fuel - not a liability.
  2. Authentic delivery: Move past performance mode and into genuine connection with your audience, every time you speak.
  3. Techniques that work: Walk away with proven methods, including Memory Bookends and the Accordion Method, for clear, engaging delivery.

  This session is designed for you if

  • Presentations, pitches, or town halls feel more draining than they should
  • You want to be more compelling without becoming someone you are not
  • You are stepping into higher-visibility roles and want to show up fully

  About the Speaker

  Diana Stepner is a Silicon Valley native who believes in the power of putting people first. She combines deep product leadership experience with a human-centered approach to help ambitious product leaders unlock their full potential.

  Diana’s background includes leadership roles across startups, enterprise organizations, digital agencies, and software consulting, including E.piphany, Cheapflights, SimplePractice, Salesforce, Monster, Pearson, Razorfish, Epsilon, and more. She holds a MIMS from UC Berkeley, an MBA from Boston University, and an ACC credential from the International Coaching Federation.

  Reserve your seat today!

  
  

  
  

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