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When Work Feels Like a Maze
A few years ago, I found myself staring at a whiteboard, trying to map out how my teams actually got work done. What started as a simple diagram quickly turned into a tangled web—lines connecting people, tools, and processes in every direction. It was a moment of clarity: our biggest challenge wasn’t a lack of effort or talent. It was the invisible sprawl that made even simple projects feel overwhelming.
If you’ve ever wondered why your team’s best intentions get lost in the shuffle, or why progress feels slow despite everyone working hard, you’re not alone. This is the reality of Work Sprawl—a problem I’ve seen up close at ClickUp and with hundreds of customers.
This isn’t just about tools or workflows; it’s about what happens when strategy loses its connection to execution.
Solving Work Sprawl: ClickUp’s GVP of Solutions and Success on AI and the Future of Work
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What Work Sprawl Really Is, and How It Breaks Strategy Downstream
Work Sprawl isn’t just about having too many apps. It’s about fragmentation—of people, processes, and technology. It feels like no one has the whole picture—and every new tool or workflow only adds another layer of complexity. In many ways, Work Sprawl is the shadow side of digital transformation, an unintended consequence of fragmented work systems.
I break it down into three buckets:
People: Teams are distributed, roles overlap, and communication gets lost in translation. Even inside one organization, teams can feel like separate islands, each with its own priorities and ways of working
Process: Workflows multiply, governance gets murky, and change management becomes an afterthought. Sub-processes and dependencies pile up, making it hard to see how work ladders up to strategy
Technology: Tools proliferate, but rarely connect in a way that gives you true visibility. The more tools you add, the more context you lose
AI is now woven through all of this. Sometimes it helps, sometimes it adds to the noise. The challenge is knowing the difference.
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The Execution Gap: The Real Cost When Strategy and Action Drift Apart
The most dangerous effect of Work Sprawl isn’t wasted time—it’s when strategy and execution lose touch. In theory, strategy should flow from leadership to every individual, and results should flow back up.
But in practice, Work Sprawl breaks this chain, often exacerbated by disconnected systems and tool sprawl.
I’ve seen teams work for weeks on projects, only to discover someone else was doing the same thing. I’ve seen leaders struggle to answer a simple question: “How does this work connect to our goals?” The larger the organization, the more pronounced the problem.
This isn’t just inefficient; it’s demoralizing. People want to know their work matters, and when they can’t see the impact, engagement suffers.
🔧 Tool overload is a hidden productivity killer
One of the biggest drivers of work sprawl is tool overload. When teams juggle too many disconnected apps, alignment and momentum suffer.
✅ 87% of high-performing teams use nine or fewer tools
⚠️ Low-performing teams are 4x more likely to use 15+ tools
📊 1 in 3 teams fall into the 5–9 tools range
The takeaway? High-performing teams keep it lean, integrate better, and maintain context—reducing noise and sprawl.
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AI: A Tool, Not a Magic Wand
AI is everywhere now, promising to automate, optimize, and transform.
But here’s what I’ve learned: AI is only as good as the context you give it.
If your AI is not contextual to your work, it’s not as effective
As you can see in the chart above, over a third of workers are using AI with zero integration into their core work areas. Many organizations are stuck with only partial or minimal AI integration, which leads to fragmented processes and missed opportunities. True full integration—where AI is seamlessly woven into daily workflows—is still rare.
If you layer AI on top of a fragmented system, you get AI Sprawl—a new set of disconnected AI tools and processes, and the result is you simply swap Work Sprawl for AI Sprawl. But when you use Contextual AI to bring people, processes, and technology together, you get clarity.
For example, at ClickUp, we use AI to surface duplicate work, connect related projects, and highlight dependencies. But we’re careful not to let AI become another silo. It’s a tool—not a replacement for thoughtful strategy or human judgment.
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Rethinking the End: AI as a Catalyst for New Possibilities
One of the most important realizations I’ve had is that most leaders (including myself) have sometimes looked at AI as a way to do the same things, only faster. We imagine AI as a turbocharger for existing processes: A plus B equals C at lightning speed.
But I believe we need to go further. AI isn’t just about speed or efficiency. It’s about rethinking what “C” even is.
Instead of asking, “How can AI help us achieve our current goals more efficiently?” we should ask, “What new goals, outcomes, and experiences does AI make possible?” It’s about thinking beyond automating the status quo to questioning it.
This means reimagining:
Organizational Structure: Moving from rigid org charts to dynamic “work charts” that reflect how value is actually created and delivered
Bodies of Work: Redefining what constitutes a project, a team, or even a job. AI can dissolve boundaries, enabling new forms of collaboration and ownership
Customer Experience: Using AI not just to speed up support tickets, but to anticipate needs, personalize journeys, and create entirely new value propositions
The leaders and teams who thrive in this new era will be those who see AI not as a shortcut, but as an invitation to rethink what’s possible.
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From Org Charts to Work Charts: A New Way to See Your Organization
Traditional org charts show who reports to whom. But they don’t show how work actually gets done. That’s why I started drawing “work charts”—maps of how projects, people, and tools interact in real life.
Work charts reveal bottlenecks, redundancies, and opportunities for collaboration. They help leaders see where strategy breaks down and where execution excels. Most importantly, they make the invisible visible.
AI can help here, too, by analyzing patterns, surfacing hidden connections, and suggesting improvements. But the foundation is always a clear, unified view of your work.
ClickUp Brain makes it easy to analyze your work, uncover hidden insights, and suggest improvements—all in one place.
Just ask a question like, “How did the customers feel in the most recent survey?” ClickUp Brain instantly summarizes key patterns, surfaces connections, and delivers actionable feedback so your team can make smarter decisions faster.
Analyze form submission data in real time and get AI insights with ClickUp
That’s why we built ClickUp Brain—the only AI assistant designed to truly understand your organization’s unique context, connect your workflows, and deliver insights where you need them most.
Unlike generic AI tools, ClickUp Brain learns your organization’s language, operates within your existing workflows, and delivers AI across all work areas from a single platform. The results speak for themselves:
ClickUp Brain delivers real results: higher integration, less frustration, and true tool consolidation
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Lessons From the Field: What I’ve Learned From Customers
Every organization’s sprawl looks different, but a few themes are universal:
Redundant work is everywhere. The most common “aha” moment is realizing two teams are solving the same problem in parallel. AI can help spot this, but only if your data is connected
Lack of awareness is costly. Teams often don’t know what’s happening elsewhere. Centralizing work isn’t just about efficiency—it’s about building trust and shared purpose
Strategy must be a two-way street. Top-down alignment is important, but so is bottom-up feedback. The best organizations create space for both
One customer told me, “We didn’t realize how much we were missing until we saw everything in one place.” That’s the power of Convergence—not just fewer tools, but more context.
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Consolidation vs. Convergence: Why Context Matters
It’s tempting to solve Work Sprawl by cutting tools. But consolidation alone can backfire if it strips away the context teams need to do their best work.
Convergence is different. It’s about bringing people, processes, and technology together in a way that preserves context and enables collaboration. Sometimes, that means fewer tools; sometimes, it means better integration. The goal is always the same: clarity.
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The Converged AI Workspace: ClickUp’s Solution
At ClickUp, we see the solution to Work Sprawl—and the path to true Convergence—as something bigger than just another tool. It’s what we call the Converged AI Workspace: a new category of work where tasks, docs, goals, and communication live together in one context-rich environment, powered by AI. It’s not just software; it’s a fundamentally different way of working.
See the complete picture of work across people, processes, and technology
Leverage AI workflow automation to surface insights, eliminate redundancies, and drive alignment
Preserve the context that makes collaboration meaningful, while reducing the noise and fragmentation from digital work systems
This is more than tool consolidation—it’s about creating a living, breathing ecosystem where strategy, execution, and innovation happen together.
📮 ClickUp Insight: 33% of people still believe multitasking equals efficiency. In reality, multitasking only increases the cost of context switching. When your brain bounces between tabs, chats, and checklists, deep focus takes the biggest hit.
ClickUp helps you single-task with intention by pulling everything you need in one place! Working on a task, but need to check the internet? Just use your voice and ask ClickUp Brain MAX to do a web search from the same window. Want to chat with Claude and polish the draft you’re working on? You can do that too, without leaving your Workspaces!
Everything you need—think chat, docs, tasks, dashboards, multiple LLMs, web search, and more—lives in one Converged AI Workspace, ready to go!
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The Human Side: Culture, Transparency, and Alignment
Solving Work Sprawl isn’t just a technical challenge—it’s a cultural one. When teams see how their work fits into the bigger picture, they’re more likely to collaborate, share knowledge, and innovate. Transparency isn’t just a buzzword; it’s the foundation for trust and agility.
At ClickUp, we’ve learned that the best ideas often come from the edges—from people closest to the work and the customer. Creating channels for feedback, celebrating cross-functional wins, and tying individual contributions to company outcomes are all essential.
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The Path Forward: Practical Steps, Not Silver Bullets
Solving Work Sprawl is a journey, not a quick fix. Here’s what I recommend:
Map your current state. Use a whiteboard, mind map, or digital tool—whatever helps you see the whole picture
Look for redundancies and gaps. Where are teams duplicating effort? Where is information getting lost?
Prioritize Convergence over consolidation. Bring work together, but don’t sacrifice the context that makes it meaningful
Integrate AI thoughtfully. Use it to enhance visibility and reduce manual work while keeping humans in the loop.
Foster transparency and feedback. Make it easy for teams to share what they’re working on and to connect their work to broader goals
Challenge your assumptions. Don’t just ask how AI can make you faster—ask what new outcomes are possible now that AI is part of your toolkit
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Making Work Human Again: From Work Sprawl to Work that Matters
Work Sprawl is a modern problem, but the solution is timeless: clarity, connection, and purpose. AI can help, but only if we use it to bring people together—not push them further apart.
At ClickUp, we’re still learning. Every day, our customers teach us something new about how work really happens. My hope is that by sharing what we’ve learned, we can help others find their own path through the maze.
If you’re struggling with Work Sprawl, you’re not alone. Start by mapping your world. You might be surprised by what you find—and by how much better work can feel when everyone is moving in the same direction.
And as we look to the future, I encourage every leader and team to ask not just how AI can help you do the same things faster, but how it can help you imagine new possibilities, new ways of working, and new definitions of success. The future of work isn’t just about speed—it’s about vision—and with a Converged AI Workspace, that vision is within reach.
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