Integrating Agile Practices into Business Strategy

Clearing the Systemic Barriers to Authentic Agility Most so-called Agile “transformations” (oh, if ever there were a misnomer) don’t fail because of the framework, tooling, or training - they fail because of deeply embedded impediments that fall into four systemic categories: Culture, Structure, Process, and Technology. These factors form a complex ecosystem, and if you treat them like separate problems, you’ll get performative agility without real adaptability. Agility isn’t a checklist or a destination. It’s a continuous journey of adaptation. Ignore the interplay between these domains at your peril. Barrier #1: Culture - The Invisible Operating System That Resists Change Problem: Traditional organizational cultures prioritize control over creativity, rewarding compliance while punishing exploration. The result is risk-averse bureaucracy. Questions: Do people feel safe admitting mistakes? Are failures learning opportunities or liabilities? Can the status quo be challenged without retaliation? Strategies: Foster psychological safety with blameless retrospectives and candor-friendly spaces. Celebrate smart failures. Promote learning with cross-functional exposure, rotation programs, and curiosity-based metrics. Barrier #2: Structure - Your Org Chart Is Showing Problem: Hierarchical, siloed structures slow decisions and disconnect teams from value delivery. Questions: Are teams aligned to customer outcomes or department KPIs? Where do decisions get made? How often do handoffs or approvals delay progress? Strategies: Align teams to value streams. Push decision-making closer to the work. Use lightweight governance and clearly delegated authority to reduce drag. Barrier #3: Process - When Following Rules Becomes Valuable Problem: Agile rituals become performative when teams confuse ceremony with value. Questions: Are Agile events energizing or exhausting? Do metrics reflect outcomes or activity? Are teams allowed to evolve their way of working? Strategies: Design outcome-oriented processes. Audit meetings regularly. Enable process experimentation within safe bounds. Focus on feedback loops, not rituals. Barrier #4: Technology - Tools as Thrust or Drag Problem: Legacy systems and fragmented tools create cognitive friction, slow feedback, and kill momentum. Questions: Do your tools promote collaboration or reporting? Can teams release frequently without manual overhead? Does tech accelerate flow or block it? Strategies: Invest in CI/CD, test automation, and self-service platforms. Retire tools that reinforce control or don't add value. Prioritize fast feedback, simplicity, and team autonomy in tool selection. Agility Isn’t Implemented - It’s Cultivated True agility requires systemic change across all four domains. It’s messy, non-linear, and context-dependent. Focus on domain interactions. Create safe-to-learn environments. Measure progress by adaptability, not just delivery. Don't chase transformation; enable evolution.

Some company cultures are just not compatible with Agile. They treat Agile as a process that can be implemented, rather than a change in mindsets, behaviors, and most of all, values of the people doing the work. Someone up top has decided that we’d better implement this Agile thing. The PMO is assigned to “go figure it out” and come back with a plan. A few months later, Agile processes are feeling heavily bureaucratic or like a bunch of checkbox exercises. There is confusion about roles and responsibilities, and things are getting messy. The problem is that you're struggling to adopt Agile methodologies at the values-level, making it feel more like a set of rules to follow rather than a different way of working altogether. It’s like your company starts up an employee baseball tournament. Only, you’re not allowed to go outside. You have to play in one of the big conference rooms. Oh, and you have to use whatever equipment you find in the supply room. The solution is to start with the values and principles behind Agile first, not the processes. The fundamental values of Agile are often in direct opposition to the established culture of the company. But by addressing the cultural blockers up front, you’ll be more likely to move toward Agile ways of working. 1) Self-organizing teams. The team is the primary unit of an Agile approach, not the individual. Decisions are often made collectively. People can switch roles or overlap without needing any permission or supervision from outside the team. The rigid culture around role definition, incentive and reward structures, and decision making will all need to be modified FIRST before you can support self-organizing teams. 2) Building in smaller increments. Teams cannot know in advance everything they need to know in order to build a working complex system, which most products and applications are. Instead, they need to start with a rough idea that includes a vision, some clear objectives, and some general constraints. Executives attempt to exert a high degree of control over everything before embarking on a project that is large and complex. Leaders will need to change the way they think about planning and funding projects to be able to adapt to Agile ways of working. 3) Adapting to change. The heart of Agile approaches is the acceptance of unknowns, and the ability to change direction based on new information coming in as we go. This is another hard pill to swallow for rigid corporate cultures. Planning has been an important part of company cultures since the days of Frederick Winslow Taylor, and old habits die hard. Executives need to get more comfortable with embracing flexibility rather than adhering to a plan. We work with leaders to help them understand, appreciate, and adopt the changes of mindset, culture, and values necessary before or during big transformations. If you're stuck in the middle of a messy Agile rollout, give me a ping and we'll talk.

Most organizations wait way too long to adopt portfolio-level agility practices. They’ve been told, “You can’t scale what’s broken,” so they wait until they nail agile at the team and product group level. What if fixing what’s broken REQUIRES focusing on the upstream that’s shaping the work and context of these teams?  Back in 2012 or so, I met an SVP responsible for a 1000-person delivery organization that was working in a traditional waterfall. Critical Chain optimized waterfall. But still. Component Teams. Heavy coordination and integration costs across multiple products. Build that takes 2 weeks to integrate. Riki and her team ran a very successful and profitable shop. However, they recognized that in order to satisfy their customers, they often had to accept change out of cycle, which created a constant fire drill. We discussed options. What Riki liked was starting with visualizing, understanding, and managing flow at the portfolio level, to break the waterfall. We got it going within weeks. (Did I mention Riki and the team were experienced, highly motivated operations-focused leaders? ). It didn’t take long for Flow times to start improving and for “Welcome Change” to be a more reasonable proposition. Over time, we’ve noticed how much “cross-product” work this portfolio delivered and started exploring ways to reorganize around value. We started introducing more and more agility principles and practices (eventually, they did reorganize to stream-aligned cross-product groups focused on the REAL product and leveraged team-level agile ways of working). Here’s the thing – Starting at the Portfolio level gives you, as a leader, tons of leverage to make an impact on the product-oriented agility of your organization – by tackling the systemic constraints to Product thinking, Flow, and Empiricism and allowing you to learn and model the behaviors you expect from your people. Yuval "Don't sleep on Portfolio Agility" Yeret