"Where do you prioritize, ruthlessly prioritize, and where do you focus your time and your energy? It's about investing in meaningful relationships and creating balance." - Alyssa Stein, Sr. Director, Cisco

In this episode, VIP guest Alyssa Stein, Senior Director at Cisco, shares a rare, grounded look at what it actually takes to step into a new leadership role with confidence, clarity, and influence.

When you switch roles, it’s not about proving yourself fast—it’s about leading wisely from day one. ⏸️ 💼

After 15 years at Google, Alyssa made a major transition—becoming “new again” at a senior level. She opens up about how she approached this shift intentionally: setting boundaries early, prioritizing what truly mattered, and resisting the pressure to over perform or over explain.

Alyssa also reflects on some of her most defining leadership moments—leading through layoffs with compassion, hosting a global leadership offsite in Cleveland, and doubling down on culture and relationships during uncertain times. Her perspective is steady, human, and deeply earned.

Throughout the conversation, Alyssa shares practical wisdom on:

• How to ruthlessly prioritize when everything feels important

• Why boundaries are a leadership strength—not a liability

• How to stay confident and influential without burning yourself out

• And how to remember that you are more than your job, even in high-stakes roles

  
  

  Key Moments

  00:15 - Alyssa's proudest career moment

  02:17 - Building culture through people and the importance of reconnecting

  03:48 - Challenging moments: navigating layoffs with compassion and support

  05:27 - The power of pause: reflecting in turbulent times

  06:48 - Resilience after burnout and the importance of grit

  08:20 - Alyssa’s "one simple thing" for maintaining work-life balance: family routines

  09:43 - Modeling kindness and empathy at home and in leadership

  13:24 - The value of ruthlessly prioritizing and setting boundaries

  16:20 - Navigating new roles and the learning curve in large organizations

  20:23 - Building relationships in remote and startup environments

  22:52 - Practical advice for visibility in fast-paced workplaces

  23:22 - Guidance for feeling stuck or stagnant: taking one step at a time

  24:37 - Closing thoughts and commitments to personal and professional development

  LINKS

  ⁠⁠Alyssa Stein - LinkedIn⁠⁠ — Connect with Alyssa for leadership insights

  ⁠Rachael's book: Pause⁠ — The concept Alyssa references for reflection and resilience

If you’re stepping into a new tech leadership role—or quietly questioning how to lead with more confidence and less self-pressure—Alyssa’s story will resonate deeply. 🌿