Initiative Roadmaps

The Problem

We spend one third of our effort on planning.

Research and experience show that organisations spend more than half their time and one-third of their effort (and therefore budget) developing detailed business cases, requirements, architecture, designs and project plans. See Phase Distribution of Software Development Effort, 2008.

Most projects are troubled or fail.

Research by the Standish Group shows that 51% of Digital projects go substantially over time, over budget and deliver less scope than expected, and 21% are cancelled or not used. Everyone who has worked in this industry for a while has seen this many times. As a consultant, it’s rare to see a large digital initiative that is not seriously troubled.

Most features aren’t used.

At the same time, Standish Group research on internal products shows that two-thirds of the features we develop are rarely or never used. Standish research is supported by recent research by Pendo, which shows that 80% of features in the typical cloud software product are seldom or never used. This research shows that we are wasting 50% to 80% of our effort on most digital initiatives.

Why this happens

Research and recent experience shows that most organisations are delivering digital initiatives in stages with or without Scrum, as shown in the Water-Scrum-Fall diagram below.

Plans and designs decay

Despite the substantial investment in upfront design and planning these initiatives typically go off the rails when the world changes or they find their planning assumptions were wrong. Projects go wrong because designs and plans decay as the environment, scope and priorities change and as we learn what the requirements and solution should be.

Agile Roadmaps are a better approach

In this article, I will show you how to bring people together for two weeks to build a roadmap that provides objectives, goals and maps for the next three to twelve months. A roadmap that builds a bridge between Agile leaders and business decision-makers so that sponsors can feel comfortable giving you the funding you need to start and lead an Agile project: a roadmap that you update continuously and every iteration in a rolling wave.

Initiative Roadmaps

“Plans are worthless, but planning is everything.” President Dwight D. Eisenhower.

Initiative Roadmaps

Over the last few years, I have developed and refined an Initiative Roadmap process that allows you to define, design and plan an initiative in weeks instead of months or years. In an Initiative Roadmap, you set your goal, strategy and direction in a high-level plan so that you can get the necessary funding and support you need to build a delivery team. When the development team starts, they evolve the plan with business stakeholders to deliver the maximum business value possible within the time and budget available.

  • Plan a new eCommerce site for an Auto Manufacturer that allowed users to customise and price cars before going to a dealer;
  • Improve the speed and performance of a Telco self-service mobile phone ordering and management portal for business customers;
  • Enhance a self-service network management portal that a Telco provides to Banks and other Enterprise customers;
  • Design and plan a knowledge management website for a Health Insurance company’s call centre staff and
  • Design and plan a new travel website for a travel company.

Before we start

Understand the problem

Initiative Roadmaps help us develop a plan to solve a known problem. If we don’t understand what problem to solve or question to ask, then we need to discover the right problem to solve. To do this, we take the brief, question the brief, develop hypotheses and plan and conduct research.

Get funding and commitment to develop a plan.

Before you start developing an Initiative Roadmap, you need to get funding and resources to do planning. In most cases, the Sponsor will prepare a presentation for executives that explains what the business problem is and why the organisation should commit resources for a few weeks to develop a plan to solve it. Some organisations may require the sponsor to go through a formal project inception process. It is not necessary to do a business case before you start an Initiative Roadmap because the Roadmap creates a detailed business case for the project.

What are Initiative Roadmaps?

An Initiative Roadmap defines where you are trying to go and how you plan to get there. It describes the team, budget, time and resources you will need. Initiative Roadmaps integrate product planning, UX design, technical architecture and initiative planning into a viable strategy to meet stakeholders expectations. Initiative Roadmaps bring senior stakeholders together with relevant experts to rapidly design and plan a new product so that you can get the funding and resources to develop it.

Designing Roadmaps

Experience shows that a small number of smart people who come together to sketch models and develop prototypes can define a viable solution design in two weeks, that is 70% to 80% right. This is an example of the Pareto principle, where 80% of the benefit is gained from 20% of the effort. The team can then iterate to 95% right through trial and error in a few months.


An Initiative Roadmap defines the:

  • Business Problem;
  • Objectives and Key results;
  • Customer Experience Roadmap;
  • Solution Architecture Roadmap;
  • Product roadmap prioritised by value, size and dependencies;
  • initiative risks and issues;
  • initiative budget based on the resource plan;

How do you develop an Initiative Roadmap?

An experienced team led by a skilled facilitator can create an Initiative Roadmap in 2 weeks. On the first day of Roadmap planning, we explain the approach, set the objectives, determine the customer journey and the feature roadmap and develop the design and technical briefs. Then we simultaneously design the product, the user experience and technical architecture. At the end of Roadmap planning, we bring it all together to estimate, prioritise the features and document our findings.

  • Define the challenge and discuss the approach
  • Define the business objectives and the key results expected
  • Define customer personas
  • Define the customer journey
  • Define the product feature map
  • Define the service blueprint
  • Define the current technical environment
  • UX sketching
  • Recruit customers for testing
  • Develop an architecture solution model
  • Define the technical POC
  • Define the UC POC
  • Define the product features
  • Develop UX wireframes
  • Develop the technical POC
  • Define the brand guidelines
  • Define the initiative risks and issues
  • Develop mood boards
  • Review and integrate the UX and Solution models with the product features
  • Develop interview scripts
  • Conduct UX testing with customers
  • Review the technical solution with architects
  • Review the UX findings
  • Review the features identified
  • Estimate feature value and size and team velocity
  • Develop a prioritised release plan
  • Write up the results as a detailed business case
  • Review the UX, Architecture and Delivery plan with stakeholders

Pitfalls to avoid

Traditional managers can inadvertently sabotage the Agile Roadmap by demanding all of the deliverables that they are used to in a conventional staged planning process. For example, they may insist on a detailed:

  • Business requirements document
  • Solution architecture document
  • Technical specification document
  • UI design document with finished wireframes and art assets for every page
  • Project Plan with a Gant chart.

What happens after the roadmap

After the planning team has developed the Initiative Roadmap, the sponsor can use it to request funding for product delivery. Or they may decide that the plan is too expensive and they need to find a cheaper way to solve their problem.

Scaling Initiative Roadmaps

You can use Initiative Roadmaps to plan large programs by mapping out big chunks of work that can be done in 3 to 6 months and then planning each piece as a separate initiative. Research by the Standish Group shows that smaller project are much more likely to be successful than larger ones, so it is always a good idea to break an extensive program into smaller parts.

Scaling your program

Rather than starting a massive program in one go, it is best to start with one team, prove that it can deliver the value expected and then split it into two groups, which divide into four and so on through a process of mitosis.

Integration Team

In programs, an integration team manages the cross dependencies between groups by developing the integrated product, architecture, UX, initiative and budget roadmaps for the next six to 12 months. This team has a Product Owner, Initiative Manager, Agile Coach, Solution Architect, UX Designer and representatives from each of the individual groups. The integration team is similar to the one defined in Scrum Nexus but with a broader focus on budgets, resourcing, architecture and UX design. The integration team will lead the development of the Initiative Roadmap for new initiatives making sure to include the people who will deliver if it is approved.


Plan faster, plan better.

Initiative Roadmaps define an approach that a Product or Project Manager can use to quickly and effectively determine the product plan, solution architecture and funding for a new initiative. With this plan, they can get budget and resources for the project, start earlier, deliver faster, increase customer satisfaction, reduce risk and realise benefits sooner.

References and Acknowledgements

Initiative Roadmaps draw on ideas from a lot of different thinkers in the Lean, Agile, Scrum, XP, Agile Architecture, UX and Design community. I owe a lot to Kent Beck and Martin Fowler for Planning Extreme Programming, Mike Cohn for Agile Estimating and Planning, Jeff Patton for Story Mapping, Scott Ambler for Agile Architecture, Eric Reiss for Lean-Agile Product Development, Jake Knapp for Design Sprints, Jeff Gothelf for Lean UX and Henrik Kniberg for Scrum and Kanban in the trenches.



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