“We are not seeing enough top-down AI transformation. We’re seeing bottom-up agent development. Most of it is useless, but it’s important to educate people. Control the sprawl and consider architecture,” said Arvind Jain, CEO of Glean.

Driving AI Culture Change: What CIO’s Need to Know

He made the remarks during his keynote interview with Jeetu Patel, president and chief product officer at Cisco, at last week’s Cisco Webexone 2026 conference.

AI transformation is driven by culture change

I followed up on Arvind’s remarks with a question at the post-keynote press conference. It featured Patel, Anurag Dhingra, SVP/GM, enterprise connectivity and collaboration at Cisco, and Snorre Kjesbu, SVG/GM of collaboration at Cisco.

I asked, “We’re not seeing enough top-down transformation work happening. Who’s doing AI transformation right, and what are they doing differently to think more strategically?”

I was building on statements I’ve made to many CIOs: AI is reshaping business, but it hasn’t transformed it yet. Many organizations overemphasize productivity and efficiency benefits, but not enough the areas driving growth, improving customer experiences, or delivering AI-enabled product/service capabilities. 

Anurag’s response surprised me, though it shouldn’t have. Their plan started bottom-up last year by giving developers unlimited tokens to experiment, and this year, by providing every Cisco employee a personal agent. But the strategy was top-down. Cisco’s leaders made an aggressive move to change the culture.  

“Most people a couple layers below get afraid their jobs will be done, so we made it easy for our people. Then we made sure to say, you have to start showing value for the token set, and now we’re at the point where everyone’s gonna have a token budget,” said Patel.

And Kjesbu closed with this memorable insight, “Curiosity, judgment, and focus have been really the key to drive this transformation [at Cisco].”

The lesson for CIOs is that AI-driven transformation starts by building on your company’s cultural strengths and addressing its weaknesses. Create a learning environment, then set top-down objectives and controls later.

Creating an environment that drives curiosity, judgment, and focus

Webex showcased several innovations and expanded collaboration strategies at the event. My three takeaways:

  • Cisco is shifting left into architecture, engineering, and construction (AEC) while working with IT and facilities to help develop the connected workplace. I saw Cisco Spaces and Cisco AI Assistant for Devices in action at their Austin Offices.
  • While many call centers are focused on increasing automation and improving deflection rates, Webex is also focused on CX to support concierge services. Webex introduced Dialog, an AI harness that enables personalized, long-lasting customer relationships.
  • The future of work requires an AI plan for CX, EX, and trusted AgenticOps. Cisco covers all three across its platforms, including Cisco Cloud Control, Cisco Data Fabric, and Splunk.

Some more of my insights are in this week’s conference report on the Driving Digital Standup.

My recent report from Splunk .conf ’26

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