Road in valley

by the Charlie Loulakis | 4 Minute Read

Building Your Roadmap to Sustain Transformation

You have seen the signs - rigid processes stifling innovation, disconnected teams blinded to customer needs, plummeting morale. The old ways of working no longer cut it. You want change but aren’t sure where to start. 

Navigating disruptive change requires focus. When gaining momentum around change for your organization, one of the best ways to help organize people is to define a roadmap that helps channel energy toward the right change initiatives at the right time. By providing visibility into what you are transforming and when, you can better. 

But what should an Agile Transformation roadmap entail? How do you instill agility systematically yet organically? Let us explore a few principles for crafting an incremental, sustainable journey to shared Agile fluency. 

Defining Your Agile Transformation Journey

Before detailing the roadmap, it helps to level-set on what “Agile Transformation” really means for your organization. Many misconstrue it as a process-only change initiative to implement frameworks like Scrum. In reality, Transformation is a far broader cultural shift in the way we work. 

At its core, a successful Agile Transformation centers on unlocking human potential. With this human focus in mind, we can define our Agile Transformation holistically: 

A company-wide journey to embed Agile principles deep in the organizational culture. It aims to make cross-functional collaboration, rapid learning & adaptation, employee empowerment, and delivering customer value the natural way of working at every level. 

This touches everything - leadership style, team dynamics, performance metrics, product management, architecture, etc.  

With the breadth of scope, we can’t (or more realistically – shouldn’t) change everything at the same time. We want to bring the right change at the right time to make meaningful, incremental progress toward our future state. 

Assessing What Change to Bring to Your Transformation Roadmap

Before defining detailed phases, we first want to focus on listening to survey the landscape of your organization. Grasping the starting point allows you to chart a journey that connects where you are today to where you aim to be tomorrow. 

At Cornerstone Agility, we focus on finding the right problems to solve before we shift to implementing solutions for our clients. We also need to be mindful of balancing the right amount of discovery (finding the right problems to solve) with incremental delivery (solving the problems). There is an art in doing just enough analysis on your transformation goals to make sure you can make an impact early and often. 

To do this, assess the current culture through observation, interviews, surveys, and data analysis. Look for pain points and bright spots on which to build. Key aspects that we want to evaluate include: 

  • People - Engagement levels? Comfort with uncertainty? Collaborative spirit? Are Roles clear and responsibilities shared appropriately? 
  • Org design – Is the way our people are structured facilitating flow? Are there silos? Bottlenecks? Bureaucratic levels? Unclear decision rights? 
  • Processes – How is value delivered? Is it efficient? Onerous? Detached from customer needs? 
  • Metrics – Are we output, or outcome focused? Lagging or leading? Enabling or constraining? 
  • Leadership – What leadership styles are driving delivery? Command and control? Micromanagers? Vision setters and coaches? Are the right voices being heard? Do we have clear objectives and strategy? 
  • Customers – Have we clearly defined our customers, and do we have feedback channels? What are the gaps between needs and offerings? 
  • Technology – How aligned is our technology and business strategy? Do our architectural processes enable flow or obstruct it?  
  • Values - Customer-centric? Is innovation fostered or feared? Responsibility valued? 

The goal here is not to spend months crafting a perfect narrative, but rather to find a great starting place that will build a backlog of high-priority transformation activities for you to begin building your roadmap. 

Creating Phases to Drive Change

Change does not happen overnight, so our roadmap is a great way of defining where we want to go and how we plan to get there. 

Keep momentum high by focusing initial energy on a few vital Transformation pillars. Master those before proceeding to the next capability. 

A sound multi-phase roadmap often looks like: 

Phase 1 - Pilots and Quick Wins 

  • Launch controlled Agile pilots to validate benefits and build expertise. Choose eager early adopter teams. 
  • Find the right people that will help champion change and focus on solutions to improve the way those people engage in their work. 
  • Identify “quick win” processes to eliminate waste and unlock people for success. 
  • Train people to spread capabilities organization-wide. 

Phase 2 - Critical Behaviors and Metrics 

  • Define the core behaviors, mindsets & metrics you aim to instill first. 
  • Coach leaders to model Agile habits in their management style. Lead by example. 
  • Align reviews/incentives to Agile outcomes vs. output metrics. Celebrate new wins. 

Phase 3 - Structure and Expansion 

  • Scale up capabilities and best practices by training more teams in Agile fluency. 
  • Adjust org structure and teams to support cross-functional cooperation. 
  • Plan and resource ongoing transformation leaders to assist in driving continuous improvement. 

Phase 4 - Optimization and Measurement 

  • Connect Agile metrics to business KPIs to guide improvement. 
  • Optimize Transformation practices based on team feedback and impact. 
  • Develop change agents and communities of practice for sustainable agility. 

Factor in the unique constraints and capabilities of your culture. But this high-level sequence moves the needle through focus, then growth, then sustainability. 

Characteristics of a Powerful Transformation Roadmap

You’ve aligned on your goals, identified the right problems to solve, and have started to phase out change to build your initial roadmap for sustained success. Now, let’s talk through characteristics of roadmaps that can help drive your transformation. Great transformation roadmaps will: 

  1. Maintain a Strategic View: The roadmap should connect transformation initiatives to overarching business goals. Leaders need to see how programs align to growth and innovation targets.  
  2. Keep Room for Variability: The closer your activities (1-2 quarters) the more specific you should be in the activities in your roadmap. But the further out you go, keep things broad. We want to drive change but do the right amount of discovery along the way to balance value delivery. 
  3. Focus on Outcomes: Group activities to showcase the outcomes you are driving to. This could include areas like Leadership Alignment, Agile Teams, and Customer Focus. Visualize interconnections. 
  4. Have Logical Sequencing: Sequence thoughtfully in priority order. Consider dependencies between workstreams. Target quick wins first to build confidence. 
  5. Show Clear Ownership: Create accountability for each step along the way. 
  6. Maintain Flexibility: The map guides but does not constraint. As new insights emerge, refine. Maintain agility in how the destination is reached. 
  7. Foster Active Collaboration: The roadmap should not be a “set and forget” activity. Share and discuss the roadmap widely and celebrate milestones along the way. 

Key Considerations When Charting Your Course

Beyond the phased sequence, several principles are vital for charting an Agile roadmap that sticks: 

  1. Win over minds, do not mandate - Prescribing Agile dogma from the top-down backfires. Instead of forcing people to change, show how change can improve their work experience. Win over people. 
  2. Design behaviors first, events second - Too often teams treat Agile as a rote checklist of rituals like standups or retros. Focus first on driving core Agile habits with emotional intelligence: customer-obsession, restlessness with status quo, hunger for feedback. Events can follow. 
  3. Coach mindsets, skills come later - Skills like writing user stories mean little without an Agile mindset. Nurture openness, accountability, and growth orientation through coaching. Then layer in skills. 
  4. Customize to your culture - Respect legacy strengths unique to your company. Frameworks are not a mandate; they are a compilation of practices. Focus on solving problems, not on blindly following frameworks. 
  5. Reflect and Adjust - What works early on may not sustain. Revisit successes frequently as the organization evolves. Great Agile roadmaps refine as they go based on feedback. 

Lastly, do not underestimate the patience required. Keep focus on why you wanted to change in the first place to help keep momentum through change. 

Transformation is a Journey, Not a Destination

Remember along the way that Transformation is not linear – the most important aspect of building and implementing your transformation roadmap is creating a plan for long-term success and sustainability. As an organization, as you drive change, you need to consider the strength of your leadership, Lean-Agile Center of Excellence, and people to make change a part of your culture.  

Keeping flexibility in your roadmap will help you solve the right problems at the right time as you adjust your coaching model to fit the needs or your maturing organization. 

Prepare to encounter the ups and downs of change as old habits creep back in. After the initial excitement fades, keeping urgency around change requires vigilance and group ownership. 

While you may be excited about the destination, focus on embracing each change in your journey! Transform leaders, teams, and culture along the way. 

Together, Embracing Change

Cornerstone Agility Inc. provides value based, principles-driven Transformation, Coaching, and Training Services built on the Cornerstone of Excellence!

Together, we take your practice beyond theory to design your blueprint for success. Our promise to you is to maintain integrity through accuracy, honesty, and trustworthiness. We offer a foundational Value Stream Workshop and a comprehensive Value Stream Identification & Mapping Workshop.

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