Podcast Summary:

How I AI – "How to get your whole team excited about AI (and actually using it)"
Host: Claire Vo
Guest: Brian Greenbaum, Product Designer at Pendo
Date: December 22, 2025

Main Theme

This episode tackles the challenge of getting entire product and design teams—not just technical folks—excited about AI and actually adopting it in their daily workflows. Brian Greenbaum shares a step-by-step, real-world playbook based on his experience spearheading an AI adoption initiative at Pendo, illustrating both the tactics and motivations behind creating company-wide momentum for AI transformation.

Key Discussion Points & Insights

1. The "Inception" Phase: Sparking Teamwide Interest in AI

• Personal Spark: While on paternity leave, Brian tried AI development tools like Cursor. He was so blown away he immediately messaged his leadership team about the need to upskill the whole product org:
  • "I had this really profound experience and I think we really need to uplevel the skill of our entire product organization. Not just designers, but also PMs." (00:00)
• Action: Even before returning from leave, he advocated for a formal AI upskilling initiative targeting PMs, designers, and others.
• Motivation: The combination of personal excitement and seeing broader business impact—internal efficiency and external thought leadership—was key to getting buy-in.
  • "You raise your hand early to take on the initiative for the organization... It's really great from a personal career perspective." — Claire (09:23)
  • "I'm having an influence way beyond my scope... If you have the initiative and the energy... it is a career builder." — Brian (10:41)

2. Brian’s Two-Prong Approach: Sync and Async

• Synchronous (Live) Sessions:
  Bi-weekly meetings covered topics with both demo/presentation and hands-on exercises.
  • Example Exercise: Everyone used Bolt New (an AI app builder) to create the same to-do list app and then "go wild" with crazy prompts, revealing the creativity and variability of AI outputs.
    • "Some of the feedback was like, wow, we all typed in the same thing...and we all got different results." (15:10)
    • _"You can give it the most wacky instructions, right?...make it look like MySpace from 2007." (16:38)
  • Purpose: Make learning fun, interactive, and safe to experiment beyond minimal viable products (MVPs).
• Asynchronous Sharing:
  • Slack channel ("Product AI") became the hub for ongoing sharing of articles, experiments, prompts, and wins.
  • Emphasis on "radical, many-to-many sharing" to defeat information hoarding and siloed learning.
    • _"Secret AI can happen because people aren't sure what they can use... and then there's information and skills hoarding..." — Claire (22:26)

3. Measuring Impact & Overcoming Obstacles

• Sentiment Surveys:
  • Used to baseline and periodically measure awareness, comfort, and actual use of AI.
  • Focused on dimensions like awareness of AI/usage policy, available tools, and perceived impact.
  • Saw strong positive shifts especially in:
    • Awareness of AI usage policy
    • Knowledge of available/approved tools
      • "The biggest gap was here because we didn't spend any time with it...what kind of data can I share within an application?" (28:45)
• Documentation:
  • Created an "AI Knowledge Center" in Confluence with:
    • List of AI tools approved for use, including data-sharing policies and how to request access
    • Resulted in faster experimentation, more transparency, and safer collaboration
    • _"If you do not have this in your org, you need it today..." — Claire (33:02)
• Leadership & Organizational Buy-in:
  • Public channels, open documentation, and visible career benefits helped snowball momentum.

4. Practical Success Stories & Culture Change

• Culture of Fun and Creativity:
  • Team embraced "play," going beyond MVP limitations and reawakening creative muscles lost to scope pressures.
    • "We've lost our muscle for asking for the magic thing...AI will let designers and PMs return to the craft." — Claire (18:32)
• Peer Sharing of Wins:
  • Example: Designer generated animated onboarding mascots using MidJourney—quick, fun, and now possible in minutes, not days or weeks.
    • _"Now we can bring life into our applications." — Brian (21:14)
• From Grassroots to Cross-org Impact:
  • Initiative spread beyond product/design, informing company-wide AI OKRs and pulling in departments like legal, IT, security for tool vetting.
  • Executive buy-in followed practical impact—led to Brian collaborating across functions and influencing wider company direction.

Notable Quotes & Memorable Moments

• The Leadership Opportunity:

  • "If you were the first designer that says, you know what, I want to figure out how our team can use AI... It's such a unique leadership opportunity to show cross functional, broad impact on teams." — Claire (09:23)

• On Getting Buy-in:

  • "There's only going to be one or two of you that get to be the leader of it...it's also really great from a personal career perspective." — Claire (09:50)
  • "This has opened so many doors... I have folks throughout the organization that are not even in product and design... looking to me as a thought leader." — Brian (10:41)

• Overcoming “Minimum Viable Mindset”:

  • "We've lost this ability to imagine. What if it did this and that? ...AI is gonna let designers and PMs return to the craft of building the awesome product." — Claire (18:32)

• Radical Transparency:

  • "Radical, many-to-many sharing...build in public...is so important for a healthy culture around AI transformation." — Claire (22:26)

Noteworthy Tactical Advice (with Timestamps)

• Make Experimentation Social & Fun:
  • (12:41–18:30) Everyone works on the same small project together, then gets creative (“go wild”) with prompts and shares what they build.
• Use Surveys to Catch and Address Fear:
  • (27:25–32:12) Sentiment surveys exposed not just knowledge gaps, but also fears—so leaders could address them directly and empathetically.
• Document the Golden Path to AI:
  • (32:12–34:52) A central, up-to-date doc listing all allowed AI tools, the data you can/can't use, procurement help, and so on.
    • "If you do not have this in your org, you need it, need it today because this is going to be the thing that changes how you work." — Claire (33:02)
• Cross-functional Allyship:
  • (33:47–34:52) IT, security, finance, procurement, and legal prioritized experiments, removing painful bottlenecks.

Success Story: The Impact of Tangible Demos

• MCP Server Project:

  • (36:15–44:08)
    Brian shared how building a small AI feature (an MCP server to auto-generate dashboards from Pendo data) let him quickly show value, get leadership attention, and accelerate adoption—despite not being an engineer.
    • "What was important was, like, I was able to demonstrate the value of this somewhat hard, opaque technology to folks that maybe didn't see it in the same way...and that has significantly impacted our roadmap." — Brian (41:36)

• Advice to Listeners:

  • Don’t let lack of engineering background be an obstacle.
  • The hardest thing is showing tangible value—"vibe code" is enough to open minds.

Lightning Round & Final Takeaways

• On Getting Unstuck When AI Struggles:

  • "Think about five other different ways that you can solve this problem and go for it." — Brian (46:38)

• Hard Skills Are (Still) Essential:

  • "This is the era of the hard skills...if you can read css, a whole world has opened up to you with these vibe coding tools." — Claire (45:41)

Timestamps for Key Segments

• 00:00 – 03:00: Brian’s personal discovery, the founding moment for AI initiatives at Pendo
• 07:49 – 12:40: Early messaging, gaining leadership buy-in, and setting the course
• 12:41 – 18:30: Launching the initiative: Two-prong approach, sync sessions and async channels
• 18:32 – 22:21: Restoring creative ambitions—AI as "fun" and as a craft tool
• 25:08 – 34:52: Measuring impact; creating documentation and internal “AI Knowledge Center”
• 36:15 – 44:08: Success stories (building MCP server), showing value internally
• 45:31 – 47:07: The need for technical understanding/hard skills for PMs/designers
• 46:21 – 46:55: Tactics for unblocking stuck AI work

Final Thoughts

Brian’s story is a true playbook for AI champions in any organization:

• Start small with excitement and a personal story.
• Build momentum through transparent, fun, peer-supported learning (sync and async).
• Secure leadership buy-in by delivering visible wins and supporting documentation.
• Empower rapid experimentation while also giving clarity on what’s approved and safe.
• Use measurement to guide and celebrate progress.
• Remember, tangible demos speak louder than perfectly engineered solutions—impact is what matters.

Find Brian on LinkedIn and discover more episodes at howiaipod.com.