Many knowledge workers engage in a daily digital scavenger hunt. They waste an astonishing 553 hours annually searching for files and documents buried in email inboxes, cloud storage, software-as-a-service (SaaS) applications, collaboration platforms, and legacy systems.1 The information sprawl problem gets worse as companies adopt more tools, and the simple act of finding what people need in order to do their job becomes a relentless waste of time and effort.

It’s not just data volumes that are a problem. The risk of inconsistency grows as new and old files are mixed. The intermixing of current and outdated information creates confusion and the risk of bad decisions. The exhausting search for answers also saps employee morale. When people can’t find what they’re looking for, they tend to seek help from colleagues, creating distractions that disrupt those workers’ concentration. One survey found that 42% of knowledge workers say they rarely spend more than an hour on productive work without interruption.2

We asked members of the CIO Experts Network — IT and business decision-makers as well as technologists and influencers — how artificial intelligence (AI) can address these issues and provide a potential lifeline. Generative AI can gather relevant data, index it, contextualize it, and make it available to knowledge workers with robust access controls. Intelligent search enables leaders to bridge data silos, streamline workflows, and give precious time back to their teams.

‘Legacy search is dead’

This new search paradigm could rapidly render conventional search obsolete. “Legacy search is dead,” declares Isaac Sacolick (@nyike), best-selling author and president of StarCIO, a digital transformation consulting firm. “Keyword search experiences often yield poor results, faceted search constrains how people explore large information repositories, and sifting through documents is inefficient.”

Sacolick believes that employees now expect experiences that summarize answers in real time, offer clickable references, and centralize information for seamless access: “IT leaders should be looking to use AI to summarize information in real time, centralize information for search, and update employee experiences.”

Providing an intelligent search experience isn’t just about slapping AI onto existing search tools, says Will Kelly, a writer focused on AI and the cloud. “IT leaders can put AI to work by using it to index and unify content across scattered platforms such as Dropbox, Notion, and Google Drive into a single searchable source of truth,” Kelly says. “But the key isn’t just adopting AI. It’s integrating it into workflows in a way that aligns with how teams collaborate.”

Chris Selland, partner at TechCXO, adds that AI-powered intelligent search can go beyond keywords to “map relationships between documents, people, and projects across platforms, creating a unified knowledge layer.” That approach makes information discoverable without disrupting existing workflows.

“AI-powered tools can also automatically categorize, tag, and extract insights from unstructured data, transforming information overload into actionable intelligence while maintaining appropriate access controls and compliance requirements,” Selland adds.

Anticipate needs

AI assistants can learn to anticipate individuals’ information needs so they can package and deliver information before a person even asks for it, according to Scott Schober (@ScottBVS), CEO of Berkeley Varitronics Systems.

“Workers lose precious time throughout the year searching for ‘stuff,’ and it’s getting worse as more tools and apps are added to help with work,” Schober says. “On top of that, people often get sidetracked while digging through the internet or shared drives.”

He believes that AI can help by tracking the location of relevant information and bringing it to users without requiring them to rummage through different applications. AI solutions can be deployed with strict security and access controls, so administrators don’t have to bear the burden of regulating each application.

“It’s like having a smart assistant who knows exactly where everything is, understands what you’re looking for, and gets it for you without making you open five different programs,” Schober says. “It’s almost as if it’s reading your mind.”

Gene de Libero, principal at Digital Mindshare LLC, envisions AI as a “time machine” that learns each worker’s unique search habits. “It connects yesterday’s Teams chat to last year’s documentation and next quarter’s project plans. AI creates custom shortcuts, making information retrieval instant instead of frustrating,” de Libero says. “It even watches how veteran employees navigate between systems, capturing these unwritten workflows and preserving institutional knowledge before it walks out the door.”

Hours reclaimed

Vivek Singh, senior vice president of IT and Strategic Planning at PALNAR, proposes a three-pronged approach: “Implement AI-powered enterprise search, intelligent document management, and custom intra-ChatGPT solutions. These tools can transform disjointed systems into a seamless knowledge infrastructure — eventually reclaiming those hundreds of wasted hours.”

Kumar Srivastava, chief technology officer at Turing Labs, dives deeper into AI’s technical advantages. “The core tenets of search quality — precision and recall — are significantly enhanced through large language models combined with intelligent prompting and context memory. This isn’t just better search; it’s smarter search that understands intent and context.”

Technology alone doesn’t solve problems — people do. Arsalan Khan (@ArsalanAKhan), a speaker, adviser, and blogger, underscores the cultural dimension of AI adoption. “To realize AI’s full value, the entire organization must understand and embrace it. IT leaders can drive this by working with vendors to unlock data from legacy systems, providing AI training and sandbox environments, and collaborating with other leaders to address the cultural aspects of AI adoption.”

Khan also stresses the importance of sandbox environments and cross-departmental collaboration to overcome resistance and ensure that AI’s benefits are widely understood and accepted.

The days of wasting hundreds of hours searching for information may finally be numbered. By leveraging AI to centralize, index, and intelligently retrieve data, organizations can move faster and focus on the work that matters most.

But success requires more than deploying new tools; it also demands thoughtful integration, user-centric design, and a commitment to cultural change. The real win comes when AI is used not just as another layer of technology but as a true partner in the modern workplace.

Learn how Dropbox Dash can help your team find, secure, organize, and share your company’s content — all in one place.


1 Economist Impact, In search of lost focus: Productivity in the post-pandemic world, 2023
2 Dropbox, Beyond the office-versus-remote debate: Why we lack focus at work and what to do about it, January 29, 2025

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