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Overcoming 5 IT Stumbling Blocks to Digital Transformation

Steven ZoBell
Workfront

The pace of business is accelerating in every industry, and digital disruptors are shaking up all the rules. To succeed and thrive, it's no longer enough to deliver great products and services at a competitive price. The businesses that truly lead will be those that can innovate faster and execute more efficiently. The writing is already on the wall — more than half of the companies in the Fortune 500 have disappeared since the year 2000, and have been replaced with more nimble competitors.

Today's organizations clearly understand the value of digital transformation and its ability to spark innovation. According to Gartner, two-thirds of all business leaders believe that their companies must pick up the pace of digitalization to remain competitive. Yet at the same time, it's surprising that fewer than half of organizations have undertaken a digital transformation project.

How can they overcome this inertia? Many organizations are taking a close look at how they approach project management. For example, the agile methodology enables organizations to break large projects down into more manageable tasks, which are tackled in short iterations or sprints.

Agile is a flexible approach that lets teams adapt to change quickly and deliver work fast. First developed for the software development industry, it's being applied across a variety of industries today. There are 12 key principles that guide agile project management, several of which focus on speed of execution and inspiring innovation, such as:

■ Customer satisfaction is always the highest priority and is achieved through rapid and continuous delivery.

■ Changing environments are embraced at any stage of the process to provide the customer with a competitive advantage.

■ A product or service is delivered with higher frequency.

■ Stakeholders and developers collaborate closely on a daily basis.

Agile has tremendous potential to unlock positive outcomes for project managers and teams, as well as customers. It can enable faster solution deployment, increased flexibility and adaptability to change, better resource utilization, and an improved focus on specific customer needs.

As IT organizations become more strategic, they are in a strong position to apply the principles of agile to lead real digital transformation within their organizations. The key to seizing this opportunity is identifying the most common stumbling blocks and moving past them. Getting started on a digital transformation initiative doesn't have to be a daunting prospect. The first steps can be as easy as focusing on simplifying processes that are highly manual, or require multiple validation steps by different groups. Look for smart ways to apply technology to improve outcomes and help streamline tasks that people do every day.

Workfront has identified five of the top challenges that IT teams face in digital transformation — and how to overcome them.

1. Lack of digital transformation strategy

IT sometimes struggles to take a position of leadership when it comes to digital transformation. A roadmap approach that identifies priorities and defines best practices can help IT expand its role and take the lead in digital transformation initiatives.

2. No visibility into work

Without insight into a project's status, team members and stakeholders can fall out of alignment. Centralizing all work within a project by collaborating in one place can provide a better view of work status, and better visibility to achieve strategic goals.

3. Work is not aligned with business goals

IT needs current, relevant data to see where projects succeed and where they fall off track. By modernizing your tech stack, collecting all data in one place and sharing data with integrated tools, your IT team can better align its initiatives with your top business imperatives.

4. Work is often delayed or slow

Too many tools and confusing processes can complicate work. By minimizing the number of tools, and automating and streamlining processes, you can build more efficient, repeatable processes, and hit deadlines faster.

5. A perception that work is inefficient and ineffective

When projects repeatedly run late or over budget, stakeholders may start to question the value of IT. Making projects more scalable and reproducible can help boost team efficiency, effectiveness, and confidence.

It's clear that digital transformation is no longer a promise on the horizon, but something that's happening here and now. According to Forrester's 2016 Global Business Technographics Data and Analytics Survey, 63 percent of global analytics decision makers surveyed stated that innovation is a high or critical priority for their organizations. By considering the top challenges that your IT organization faces today, and taking the initiative to move beyond them, you can move your organization several steps forward on its journey to digital transformation.

Steven ZoBell is Chief Product & Technology Officer at Workfront

The Latest

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

In MEAN TIME TO INSIGHT Episode 23, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses the NetOps labor shortage ... 

Technology management is evolving, and in turn, so is the scope of FinOps. The FinOps Foundation recently updated their mission statement from "advancing the people who manage the value of cloud" to "advancing the people who manage the value of technology." This seemingly small change solidifies a larger evolution: FinOps practitioners have organically expanded to be focused on more than just cloud cost optimization. Today, FinOps teams are largely — and quickly — expanding their job descriptions, evolving into a critical function for managing the full value of technology ...

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.

The quietest week your engineering team has ever had might also be its best. No alarms going off. No escalations. No frantic Teams or Slack threads at 2 a.m. Everything humming along exactly as it should. And somewhere in a leadership meeting, someone looks at the metrics dashboard, sees a flat line of incidents and says: "Seems like things are pretty calm over there. Do we really need all those people?" ... I've spent many years in engineering, and this pattern keeps repeating ...

Overcoming 5 IT Stumbling Blocks to Digital Transformation

Steven ZoBell
Workfront

The pace of business is accelerating in every industry, and digital disruptors are shaking up all the rules. To succeed and thrive, it's no longer enough to deliver great products and services at a competitive price. The businesses that truly lead will be those that can innovate faster and execute more efficiently. The writing is already on the wall — more than half of the companies in the Fortune 500 have disappeared since the year 2000, and have been replaced with more nimble competitors.

Today's organizations clearly understand the value of digital transformation and its ability to spark innovation. According to Gartner, two-thirds of all business leaders believe that their companies must pick up the pace of digitalization to remain competitive. Yet at the same time, it's surprising that fewer than half of organizations have undertaken a digital transformation project.

How can they overcome this inertia? Many organizations are taking a close look at how they approach project management. For example, the agile methodology enables organizations to break large projects down into more manageable tasks, which are tackled in short iterations or sprints.

Agile is a flexible approach that lets teams adapt to change quickly and deliver work fast. First developed for the software development industry, it's being applied across a variety of industries today. There are 12 key principles that guide agile project management, several of which focus on speed of execution and inspiring innovation, such as:

■ Customer satisfaction is always the highest priority and is achieved through rapid and continuous delivery.

■ Changing environments are embraced at any stage of the process to provide the customer with a competitive advantage.

■ A product or service is delivered with higher frequency.

■ Stakeholders and developers collaborate closely on a daily basis.

Agile has tremendous potential to unlock positive outcomes for project managers and teams, as well as customers. It can enable faster solution deployment, increased flexibility and adaptability to change, better resource utilization, and an improved focus on specific customer needs.

As IT organizations become more strategic, they are in a strong position to apply the principles of agile to lead real digital transformation within their organizations. The key to seizing this opportunity is identifying the most common stumbling blocks and moving past them. Getting started on a digital transformation initiative doesn't have to be a daunting prospect. The first steps can be as easy as focusing on simplifying processes that are highly manual, or require multiple validation steps by different groups. Look for smart ways to apply technology to improve outcomes and help streamline tasks that people do every day.

Workfront has identified five of the top challenges that IT teams face in digital transformation — and how to overcome them.

1. Lack of digital transformation strategy

IT sometimes struggles to take a position of leadership when it comes to digital transformation. A roadmap approach that identifies priorities and defines best practices can help IT expand its role and take the lead in digital transformation initiatives.

2. No visibility into work

Without insight into a project's status, team members and stakeholders can fall out of alignment. Centralizing all work within a project by collaborating in one place can provide a better view of work status, and better visibility to achieve strategic goals.

3. Work is not aligned with business goals

IT needs current, relevant data to see where projects succeed and where they fall off track. By modernizing your tech stack, collecting all data in one place and sharing data with integrated tools, your IT team can better align its initiatives with your top business imperatives.

4. Work is often delayed or slow

Too many tools and confusing processes can complicate work. By minimizing the number of tools, and automating and streamlining processes, you can build more efficient, repeatable processes, and hit deadlines faster.

5. A perception that work is inefficient and ineffective

When projects repeatedly run late or over budget, stakeholders may start to question the value of IT. Making projects more scalable and reproducible can help boost team efficiency, effectiveness, and confidence.

It's clear that digital transformation is no longer a promise on the horizon, but something that's happening here and now. According to Forrester's 2016 Global Business Technographics Data and Analytics Survey, 63 percent of global analytics decision makers surveyed stated that innovation is a high or critical priority for their organizations. By considering the top challenges that your IT organization faces today, and taking the initiative to move beyond them, you can move your organization several steps forward on its journey to digital transformation.

Steven ZoBell is Chief Product & Technology Officer at Workfront

The Latest

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

In MEAN TIME TO INSIGHT Episode 23, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses the NetOps labor shortage ... 

Technology management is evolving, and in turn, so is the scope of FinOps. The FinOps Foundation recently updated their mission statement from "advancing the people who manage the value of cloud" to "advancing the people who manage the value of technology." This seemingly small change solidifies a larger evolution: FinOps practitioners have organically expanded to be focused on more than just cloud cost optimization. Today, FinOps teams are largely — and quickly — expanding their job descriptions, evolving into a critical function for managing the full value of technology ...

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.

The quietest week your engineering team has ever had might also be its best. No alarms going off. No escalations. No frantic Teams or Slack threads at 2 a.m. Everything humming along exactly as it should. And somewhere in a leadership meeting, someone looks at the metrics dashboard, sees a flat line of incidents and says: "Seems like things are pretty calm over there. Do we really need all those people?" ... I've spent many years in engineering, and this pattern keeps repeating ...