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What One Cybersecurity CEO Learned From Getting His Team To Embrace AI — One Lunch At A Time

At ImageQuest, casual lunchtime curiosity sessions sparked an AI strategy that turned skeptics into innovators — and helped even cautious clients move forward with trust.

Dr. Gleb TsipurskybyDr. Gleb Tsipursky
July 2, 2025
in Tech
Reading Time: 5 mins read
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What One Cybersecurity CEO Learned From Getting His Team To Embrace AI — One Lunch At A Time

In a cautious industry, one company turned AI fear into progress by starting small, inviting dialogue, and focusing on low-risk, high-value use cases.

In the cybersecurity and advisory services industries, staying ahead of technological change is a necessity. Milton Bartley, CEO of ImageQuest, a Nashville-based security services firm specializing in regulated industries like community banks and wealth management companies, has taken a proactive approach to the disruptive force of generative AI. 

In a candid conversation, Bartley shared how he tackled internal adoption, client resistance, and changes in regulations — one lunch at a time.

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Planting the Seeds of Curiosity 

When generative AI burst into public consciousness, Bartley and his team at ImageQuest were already well into their experimentation phase. 

“We became early adopters two and a half years ago,” he recalled. 

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Rather than waiting for a perfect moment, Bartley and his CIO sought out business use cases where they could either pilot or fully integrate AI. Their efforts were not without internal hurdles. While some employees eagerly embraced the possibilities, others were hesitant. 

Bartley described the adoption curve within ImageQuest as “a typical bell curve,” with 10% of employees leading the charge, 10% resisting, and 80% in various stages of curiosity and caution. 

Recognizing the need to shape this middle ground, ImageQuest introduced a monthly, voluntary lunchtime gathering where staff could share ideas, successes, and questions about using AI in their work. 

These sessions, sometimes formal lunch-and-learns and sometimes casual meetups, became a cornerstone of building a culture of innovation without the pressure of mandates. 

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“We really believe that the best ideas come from the people who do the work,” Bartley emphasized. This grassroots approach fueled a spirit of exploration and demystified AI for employees who might otherwise have stayed on the sidelines. 

“This grassroots approach fueled a spirit of exploration and demystified AI for employees who might otherwise have stayed on the sidelines”.

Creating Structure Without Stifling Innovation 

Early enthusiasm at ImageQuest needed to be channeled carefully. 

Bartley recounted how his CIO, a longtime user of automation technologies, would sometimes move too fast, implementing solutions before getting buy-in from other stakeholders. Recognizing this, Bartley introduced lightweight governance measures to ensure excitement did not outpace thoughtful risk management. 

The cornerstone of this governance was a simple but robust AI policy added to ImageQuest’s broader technology use policies. Rather than restricting innovation with heavy-handed rules, the policy provided a flexible framework: employees could freely use approved tools as long as they avoided uploading sensitive client or company data without explicit permission. 

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In addition, Bartley established an internal AI committee, initially composed of five or six employees, to evaluate use cases, guide internal deployments, and explore how to assist clients with their AI journeys. 

Over time, the committee’s role evolved, but it remained a critical engine for responsible and effective innovation. 

Notably, Bartley’s approach always balanced technical safeguards with human factors. 

“We didn’t want to slow down momentum with bureaucracy,” he explained, “but we needed everyone to understand the guardrails we had to operate within.” 

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Translating Innovation to Client Success 

While ImageQuest employees warmed to AI through deliberate exposure and structured freedom, clients — particularly highly regulated banks — presented a different challenge. 

Bartley categorized client reactions into three broad groups: the cautious followers, the fearful avoiders, and the thoughtful pragmatists. 

The cautious followers preferred to wait for peer institutions to adopt AI before moving forward. Fearful avoiders, overwhelmed by a lack of internal expertise and regulatory uncertainty, opted for blanket rejection. Thoughtful pragmatists, meanwhile, worked with ImageQuest to identify safe, high-value opportunities for AI deployment that posed little or no regulatory risk. 

Bartley offered practical examples of how ImageQuest guided clients to safe use cases. 

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For instance, banks could leverage AI to modernize standard operating procedures and job descriptions — tasks that steer clear of sensitive client data and regulatory scrutiny. 

On ImageQuest’s own side, the team developed AI-driven workflows that dramatically reduced administrative burdens. A prime example was the vendor management process. Rather than manually combing through hundreds of pages in SOC reports, AI agents now identify specific compliance indicators instantly, allowing human analysts to focus their expertise on validation rather than tedious search tasks. 

“It’s about taking a ten-mile journey and giving people a head star”.

“It’s about taking a ten-mile journey and giving people a head start, so they can focus their energy on the last mile where their real value lies,” Bartley said. 

This philosophy not only preserves job security but enhances it, reframing AI not as a replacement for employees but as a force multiplier for their skills. 

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Looking Ahead: A Future of Agents and Acceleration 

As generative AI matures and agentic AI rises on the horizon, Bartley sees a future shaped by rapid, transformative change. He described the trend as happening “slowly, then suddenly,” noting how AI is already embedded into the core offerings of major banking software providers. 

Looking forward, Bartley predicts that agentic AI — the next generation where AI agents independently complete tasks without human initiation — will be the true inflection point. 

“We’re going to wake up one morning, maybe six weeks from now, and agentic AI will just be here,” he said with a mix of excitement and inevitability. 

Despite the pace of change, Bartley remains grounded in his approach. Rather than pursuing flashier, high-risk applications, he continues to prioritize incremental efficiency gains that build client trust and internal competence. The emphasis is on actionable, practical AI…not the hype. 

At ImageQuest, creating a culture of Gen AI curiosity is not about chasing the next big thing. It is about patiently nurturing an environment where employees and clients alike feel empowered to explore, innovate, and ask tough questions. 

And sometimes, all it takes to spark that culture is a casual lunch conversation and a willingness to listen. 

In a world eager for instant transformation, Bartley’s model of steady, thoughtful adoption stands out. 

It offers a reminder that sometimes, the most profound change begins with simply making space for curiosity — and then letting it grow. 

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Dr. Gleb Tsipursky

Dr. Gleb Tsipursky

Lauded as “Office Whisperer” and “Hybrid Expert” by The New York Times, Dr. Gleb Tsipursky helps leaders use hybrid work to improve retention and productivity while cutting costs. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote the first book on returning to the office and leading hybrid teams after the pandemic, his best-seller Returning to the Office and Leading Hybrid and Remote Teams (Intentional Insights, 2021).

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