Isaac Sacolick
Contributing writer

5 signs your agile practices will lead to digital disaster

Sep 20, 20239 mins
Agile DevelopmentDigital Transformation

Digital transformation is often an organization’s big bet for changing its business trajectory. Agile can help IT leaders get there — but only if undertaken in service of digital objectives.

Teamwork, project management, agile methodology. Two young business women in the office are planning product development and support. Colleagues glue sticky stickers on the Board
Credit: Trismegist san / Shutterstock

CIOs are under increasing pressure to deliver more digital innovations faster and more efficiently. Business leaders expect IT to develop new products, improve customer experiences, automate workflows, and deliver new artificial intelligence capabilities.

To do so, CIOs must continuously improve their product management, program management, and delivery capabilities to wow customers and deliver competitive advantages, all while steering clear of surefire DX mistakes such as prioritizing too many initiatives and underinvesting in developing digital trailblazers

Many IT teams use agile methodologies to iteratively deliver feature-rich releases, improve capabilities, address technical debt, and experiment with emerging technologies. But speaking to many IT leaders, there are often gaps between how IT runs Scrum, Kanban, or other agile practices and what CIOs need in order to achieve digital transformation objectives.

I recently moderated Adaptavist’s “Agile Back to Basics” roundtable, which included three authors of the Agile Manifesto. We discussed how many agile teams focus on rituals without truly understanding the manifesto’s objectives or the organization’s goals. Their comments offer insights as to what to do if your teams are “doing agile” but aren’t agile enough to deliver digital transformation results.

Below are five key issues organizations often have when undertaking agile methodologies to fuel digital transformation.

1. You’ve failed to build trust and communicate the vision

Tina Behers, vice president of enterprise agility at Aligned Agility, shared two key prerequisites organizations need to execute digital transformation initiatives with agile methodologies. “If the organization has little to no trust, especially between software development teams and management or your executives and anyone under them, the transformation of anything will not work,” she said.

Agile can help build trust between teams, stakeholders, and leadership, but agile cannot correct a lack of trust between people. CIOs should not assume there’s sufficient trust between leaders and teams and psychological safety for people to work without unnecessary stress. CIOs and digital transformation leaders should openly discuss the importance of trust, ensure room for learning from failures, and schedule team-building programs.

Another prerequisite is ensuring agile teams understand the vision and goals of the digital initiative from the outset. “If the executive of the organization, whether that’s the CEO or the head of product, has not published and communicated several times what the vision and the strategy are for the company or the product, there is no way for the product managers to set the priorities, and therefore there’s no way for the teams to be able to deliver value realistically,” Behers added.

The best way to address this gap is to draft a simple vision statement written by product managers and delivery leaders in collaboration with stakeholders and agile teams. The writing process builds trust, and a documented vision builds a shared understanding of priorities. Equally important, the documented vision is a tool for agile teams to make implementation decisions when there are multiple ways to solve problems, each with different benefits and tradeoffs.

2. You’re retaining waterfall planning but demanding agile delivery

With your vision statement in hand, planning is the next vital step, which includes speaking to customers, defining problem statements, reviewing operational data, and conducting proof of concepts. 

Unfortunately, organizations too often define planning as a pre-agile business activity, an artifact from waterfall project methodologies where planning helped define requirements, timelines, costs, and other factors before leaders were ready to make investments.

“Business leaders get scared and say, ‘Tell me the plan so I can sleep at night,’” said Ronica Roth, co-founder and principal of The Welcome Elephant. “They are afraid of failure and the uncertainty of knowledge work, and so that’s stressful. Agile is an amazing risk management tool for managing uncertainty, but that’s not always obvious.”  

The key is recognizing that planning must be an agile discipline, not a standalone activity performed independently of agile teams. Agile planning practices include prioritizing backlogs every sprint, writing short user stories with acceptance criteria, and conducting retrospectives. Many organizations will also estimate user stories and undertake other continuous planning practices.

Digital transformation initiatives are often the organization’s big bets to change the business and operating model. The strategic importance of these initiatives creates even more tension for CIOs and their teams to answer what will be delivered and when.   

“Leadership has a right to ask agile teams when something will be delivered and how much it will cost, but teams have a right to push back on unrealistic expectations,” said Jon Kern, agile transformation consultant and co-author of the Agile Manifesto.

The tension can undermine trust, prevent teams from focusing on transformational objectives, and destabilize the environment teams need to succeed in the longer term. “I want my teams to be thrilled about putting smiles on the customers’ faces, delivering value, and having fun doing it,” Kern added.

According to Tim Ottinger, senior consultant at Industrial Logic, leaders need to get back to basics when there’s tension between defining timelines and committing to big-rock objectives. “The first three words are the best in the manifesto: We are discovering. I think that many people lose this context,” he said.

3. Your agile principles are too vaguely defined

Beyond the tension between leadership and teams, there is often a secondary tension across and within agile teams.

James Grenning, co-author of the Agile Manifesto, said, “Agile adoptions usually start with introducing iterative management, but we can’t expect development teams to know iterative engineering instinctively. There are skills to learn and master, and technical excellence is a key factor to successful agile adoption.”

Today’s agile organizations are staffed with employees, contractors, and freelancers who have experienced different agile frameworks, methodologies, and tools. What are the decision-making authorities? What are the organization’s agile principles? Where can teams self-organize and make decisions? What practices are standard?

Our “back to basics” conversation led to several insights about where organizations often fall short on practicing agile effectively in support of their digital initiatives, including the following:

  • Missing the point on key agile principles: “99% of agile shops don’t have a cross-functional team, and they aren’t self-managing. It was written right there on page two of the manifesto,” Ottinger said.
  • Allowing self-organization to overrule business sense: “If we just leave the team to their own devices because they’re self-organizing, in a couple of weeks, we’ll probably see that the checks aren’t cashing anymore. Agile has to work within the context of the organization, whether it’s the process of financial reporting, estimation, or forecasting,” said Phil Heijkoop, general manager of Aligned Agility.
  • Getting drunk on metrics: “Sometimes we get overly zealous about our metrics, have too many of them, and try to measure too many unmeasurable things,” said Jim Highsmith, co-author of the Agile Manifesto. He recommends that leaders identify a metric that focuses on value to the customer.

Digital transformation initiatives often require the coordination of multiple agile teams, so misaligned expectations on principles, team authorities, and standards lead to conflicts. The challenge for CIOs and agile leaders is to create a structure and process for an agile center of excellence chartered with evolving the organization’s agile principles and standards.

4. You treat change management and feedback as afterthoughts

Agile teams, especially ones using CI/CD and other devops practices to enable continuous deployment, can easily leave out key practices required in digital transformation initiatives.

Agile teams aren’t done when they deploy the code. Successful transformations require change management activities to ensure end-user adoption, capture meaningful stakeholder feedback, and review operating metrics.

Are these activities within the scope of agile programs? If not, the disconnect can lead to poor end-user satisfaction and angry stakeholders. Additionally, agile teams operating without customer feedback may overengineer features and miss opportunities to realign priorities.   

Here, Kern offered one suggestion. “Tell people to think of the smallest thing they can do and then do something slightly uncomfortably less. You can always add more, but you can never get back the wasted time. Aim to fall a little bit short and get some early feedback.”

5. You’re ignoring the culture aspect of agile — or not aligning it with business objectives

Transformation requires a culture change for people to look beyond how things work today and to challenge assumptions. Agile leaders seek agile mindsets and cultures, but defining what this means in the context of digital transformation goals should be on the CIO’s agenda.

One example paradigm to avoid in defining agile culture is “we’re not agile enough” without aligning process improvement to business objectives. A second, and my pet peeve, is hearing teammates say, “That’s not agile,” and I share several stories around this anti-pattern in my book Digital Trailblazer.

So, how can CIOs define an agile mindset in their organizations? “An agile mindset is developing habits through our behaviors, and those behaviors must be pervasive across the organization,” said Behers.  

And how can CIOs know when trust and an agile mindset are forming across the organization? Roth answered, “The conversation between agile teams and stakeholders shifts to the right one, which is not about the team’s capacity but instead is about the priority of the work.” 

Highsmith added, “The purpose of an agile mindset is to prepare us for a turbulent future.”

For CIOs looking to accelerate digital transformation and improve business outcomes, aligning agile methodologies and seeking an agile culture can be a game-changer.

My recommended CIO action plan:

  • Require vision statements for all digital transformation initiatives.
  • Apply agile methodologies to the full lifecycle of an iterative program, including planning, delivery, change management, and communications.
  • Create an agile center of excellence chartered with evolving self-organizing principles and standards.
  • Lead the discussion on what an agile mindset and culture should mean in your organization.

There isn’t a one-size-fits-all playbook for agile methodologies or digital transformation, and success requires the CIO to take on many leadership responsibilities.

Isaac Sacolick
Contributing writer

Isaac Sacolick, President of StarCIO, a digital transformation learning company, guides leaders on adopting the practices needed to lead transformational change in their organizations. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites.

The opinions expressed in this blog are those of Isaac Sacolick and do not necessarily represent those of IDG Communications, Inc., its parent, subsidiary or affiliated companies.

More from this author