Why Organizations Struggle to Reap the Benefits of Agile

August 28, 2023 | By Claudia Fetter

Why Organizations Struggle to Reap the Benefits of Agile

The shift to Agile is a journey, not a destination. It’s important for organizations to understand the criticality of committing to the full journey, and the need for a concerted, concentrated effort to do so.

Unfortunately, poorly implemented Agile adoption efforts lead organizations to the wrong assumption: Agile does not deliver promised benefits.

The reality is that poor upfront investment in Agile practices leads to poor results. However, this can be avoided by identifying where Agile adoption typically fails and mitigating the potential for unrealized results.   

Let’s explore a few ways organizations typically hamper their Agile journey, and how alternative Agile adoption approaches can help organizations realize different outcomes.

Lack of Investment in Skill Development

Organizations that invest in technology without properly investing in upskilling and reskilling the talent responsible for implementation are akin to putting a driver without racing experience on an F1 circuit. Covering the required distance quickly and safely is understood, but the rules for driving are very different.  

All too often, staff are expected to learn “real-time” about the new technologies they are now responsible for, with little training or clearly established performance expectations. Lack of training severely limits the team’s ability to be Agile; team members cannot effectively collaborate and coordinate on new technology rollouts nor problem-solve issues (which undoubtedly will occur) if they aren’t sufficiently skilled. Under significant pressure to deploy, engineers default to keeping the system operational rather than healthy. 

Additionally, training investments need to cover both Agile and technical skill sets. Generally, organizations pay for technical certifications and an introductory “101” Agile course that covers the basic concepts and tenets of Agile. Unfortunately, introductory courses tend to fall short of the critical skill development necessary for staff to realize the benefits of Agile.  

Since Agile is rooted in behavioral change – a way of analyzing, being, and interacting – it’s best to not short-change the upskilling investment required for Agile adoption. Agile is not a knowledge-based concept to learn in the classroom; it entails a distinct set of skills (e.g., systems thinking and planning, communications, facilitation, and structured process development, to name a few) that requires active application to learn and adopt. Good training needs to support staff through the practical experience of applying Agile on the job and throughout the various stages of the software development lifecycle. Ideally under the guidance of seasoned Agilists who can steward new team practices and processes.   

Moreover, any Agile training initiatives should also help bridge interactions between the Business and technical teams and support scaling Agile across the organization. Agile processes and practices emphasize coordination and cross-functional collaboration, including with the Business, to deliver not just features at high velocity, but quality functionality that avoids the costly downstream effects of technical debt. Although Agile originated from engineers looking to improve development processes, it is applicable to all facets of an organization. Agile training should integrate the Business into any adoption process so that all stakeholders understand the impact of effective planning, user-centric development, and resource alignment on customer satisfaction, cost savings, technical debt reduction, and Business outcomes.  

Consider bringing in seasoned Agile experts or outsourcing Agile consultants to build your Agile capability, including training resident Agile Coaches so that an in-house pool of experts can sustain initial gains, especially during future modernization efforts. Underestimating the investment in this unique skill set is akin to underinvesting in a critical success factor for service delivery and customer/user satisfaction.  

However, factor in the timing of introducing teams to Agile, ideally before undergoing a significant technical transformation. Given Agile supports cross-functional collaboration when it’s needed most, during times of high uncertainty, investing in Agile before major technical disruption ensures practices are in place to help overcome the challenges with any transformation. 

Allowing Space for Experimentation & Failure

A critical aspect of Agile is allowing teams space for experimentation and learning.  Often the tech industry speaks of “fail fast, fail often”, but this quip is a misnomer as it fails to capture the true value-add that experimentation yields. Instead, “learn fast, learn often” would be more appropriate, assuming Agile is practiced effectively. 

Experimentation is inherently iterative rounds of development to produce successful software or an automated infrastructure solution, but each round always produces learning that shapes the team’s approach to a problem going forward. Providing teams opportunities to cumulatively build essential technical knowledge and hone analytical, problem-solving, and creative thinking skills—so critical to solution design and development—is a key ingredient to the “secret sauce” of highly effective teams.  

Agile intends to develop autonomous, self-directed teams, based on good communication, ideation, knowledge exchange, and feedback loops, so that the inherent abilities and collective learning of the team contribute to increasing mastery over time and emergent creativity for optimizing technology. An Agile mindset requires time and practice to incubate and yield different results.

There are two things to consider when determining the investment required for your Agile implementation: 


      1. Is your organization prepared to take on and integrate Agile?
        Leadership needs to take an honest assessment of the organizational structure and resident capability or gaps available to support the introduction of Agile. Many organizations are structured along functional or domain disciplines, aligned to support reporting channels rather than cross-functional collaboration and effective communication channels. 

    Additionally, system engineers are not typically trained in process reengineering, and face the double challenge of adapting current processes and practices to Agile without sufficient subject matter expertise in Agile to make or lead the transition. Quite a herculean task given they are still accountable for production. 

    Shifting to Agile is a transformation that entails breaking silos, changing performance standards, and introducing new processes. Understanding the maturity of your current Agile practice is essential to defining the gaps and determining how best to implement the desired change. Training is important but may be insufficient if the organizational structure and operations allow anti-patterns to dominate and interfere with adoption.


        1. Is your culture ready for Agile? 

       “Culture eats strategy for lunch.” 

      Peter Drucker

      Culture is one of the most overlooked aspects of any Agile implementation, and yet is a strong determinant of how easy or challenging the transition will be. Agile inherently requires shifts in team interactions, processes, and behavior; if a culture is traditionally hierarchical, a matrixed cross-functional teaming model that depends upon information-sharing and fluid lines of communication will deviate significantly from the existing operating model. By contrast, an entity that is flatter and values individual contribution and ideas will probably be more likely to adapt and integrate Agile practices, at least within a shorter time frame.  

      In preparation for such a transition, leadership needs to take stock of the culture that staff actually to experience daily, not the values espoused on marketing materials or in strategic plans. All too often, the espoused values are different than those practiced and rewarded. For example, “top-down” decision-making may mean management drives software project outputs and timelines irrespective of accumulating technical debt. The message for staff? Business objectives trump organizational values; courage to challenge growth targets in service of well-built functionality and long-term customer interests is not rewarded.  The implicit message is a power imbalance, with Sales targets valued more than engineering expertise and standards. By contrast, Agile-based values place a premium on customer interactions and collaboration; if the organization puts these values into practice, are technical teams involved as equal partners in the cost-benefit analysis of possible technical approaches for meeting business needs? 

      Values of customer-centricity, courage, and performance excellence are most evident to staff when operationalized through daily practices, especially when it comes to communication and collaboration.  Daily practices determine how comfortable teams feel about surfacing problems – should they expect retribution or appreciation for avoiding potentially costly technical debt? What behaviors are rewarded, and which are reinforced implicitly says a lot about a culture. These types of issues surface the actual values that are enforced explicitly and implicitly and determine the extent to which an organization is predisposed to Agile or only beginning the culture shift required for full adoption. 

      Organizational patterns of communication, learning, and rewards are all good predictors of the degree to which the culture supports employees’ transition to Agile. Does the culture already support employees in understanding the purpose of their work, mastering key skill sets, and working independently and creatively on resolving core business and technical problems to advance strategic objectives? Culture is a critical pillar or inhibitor of the very attributes deemed foundational to Agile; the sooner leadership understands where their organizational culture falls on the spectrum of readiness for Agile, the better it can avoid the common pitfalls of Agile implementation and invest in the right activities to support the transition. 

      Consider conducting a digital business transformation assessment to understand the current state of how the Business and IT operate, the degree of readiness for change and Agile, and the priority actions to initiate implementation of Agile and implant it as a bedrock of operations across product development teams.

      Fundamentally Divergent Understanding of Development between IT and the Business

      A conducive environment for Agile adoption is linked, in part, to the Business and IT sharing a vision on the kind of technical and process investments required to realize modern service delivery. Unfortunately, many organizations still consider and treat IT as a “back office” cost center to be made efficient and less expensive rather than as a core capability integral to delivering essential services. This paradigm positions IT as overhead, to be managed closely rather than perceived as a value-added investment. As a result, IT fails to receive the requisite resources to overcome accumulating technical debt, prohibiting migration away from legacy systems. This anti-pattern perpetuates IT’s inability to overcome inefficiencies to meet project timelines and budget parameters. In effect, this cyclical pattern of underinvestment leads to unmet expectations and reinforces the Business’ perception that IT is a liability to market success.  

      However, modern technology practices, including Agile, allow IT to be an equal partner and service provider, supporting Business objectives earlier, faster, and better.  The paradigm shift depends upon the requisite investments to fund modern tools AND processes and practices so IT can “build the right thing, and build the thing right”.  Investing in Agile ensures the Business and IT jointly engage in decision-making around trade-offs between building new services versus solving yesterday’s technical challenges rooted in legacy systems that no longer meet market demands. Providing the highest value to customers involves the Business and IT aligning on customer/user needs, jointly prioritized product or service functionality, and a joint technical roadmap for how to approach component development. The cross-functional (inter-departmental and intra-departmental) collaboration required to realize this paradigm shift leverages Agile to break functional silos, establish new communication channels between IT and the Business, and build processes that allow for ongoing delivery of improved service quality at a faster pace.  

      Agile emphasizes building the most valuable components of a system first, and adding enhancements as the development team learns about customer/user needs and overcomes unforeseeable issues common to most technology projects. Priorities may shift as user acceptance testing challenges initial assumptions and the team revisits requirements and timelines for functionality. Despite affording the Business a steady incremental release of product features that can be tested with users, this can feel risky and unpredictable for those vested in the traditional triple constraints—scope, cost, and time— approach to project management. In this regard, the Business needs to partner with engineers to determine how best to address any shift in requirements and adapt schedules accordingly, rather than keep to a plan that no longer serves the customer/user base. If the Business and IT are not synchronized on objectives, the roadmap to get there, and key variables that impinge on system milestones, then an adversarial relationship develops that is an anti-pattern to successful service delivery.

      Benefits Require Investment

      So what should we take away? To reap the benefits of agile, you MUST properly invest in not only the technology but also the people and processes that can exploit the power technology affords. Essentially, organizations fail to realize desired results without investing in the type of skill proficiency and experiential learning that improves product planning, delivery speed and quality, and adaptive problem-solving that can address unforeseen barriers to production. 

      Outsource expertise that is not a core internal capability, but also plan to provide ongoing support on a sustained basis throughout implementation so that teams are properly organized, trained, and adopting the practices that will enable them to achieve desired performance targets. Oteemo’s enablement approach brings seasoned, senior experts to provide formal and informal training and coaching using a methodology that incorporates ongoing projects. Oteemo advocates immersing teams in the application of Agile behaviors and DevSecOps practices, jointly developing work products that capture the logic behind technical decisions and provide singular sources of design and architecture truth.  

      Learning through collective, cross-functional team engagement in decision-making, real-time during training provides teams with unified references and incubates collaboration essential for reaping the benefits of Agile and DevSecOps.


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