DSRUPTR Guide: Effectively Developing a Digital Product Strategy and Roadmap

Many companies go through Agile training and deploy a massive organizational effort into transforming their development teams – even business units – using Agile to develop digital products and experiences.

And then the first day of Sprint 1 starts… and everyone’s still confused.

img - dilbert agile confusion

Some of the biggest problems I’ve seen – both working in and coaching teams – is that most Agile teams still aren’t prepared and don’t know what to do in Sprint 1.

This is primarily a function of the Agile framework exclusively focusing on the development process, and not providing direction on fundamental product, business, or design needs.

This is where Strategic Product Planning can really be effective in strategizing, planning, and preparing your team for Sprint 1.


Strategic Product Planning

Strategic Product Planning is the optimal method to begin the process of developing a digital product, because it will provide the strategy and roadmap to guide your Agile team in Sprint 1 and beyond.

It typically lasts 2-4 weeks, where your Agile team leaders (Product Manager, Design Lead, Dev Lead) – working in collaboration with executive leadership – assess if the product has potential in the broader market, and then develop a strategy to guide the team and broader company.

img - agile development phases

There’s a lot that goes into product planning, so I’ll break the Strategic Product Planning responsibilities down by role…


title - leadership

Typically in large mature companies, digital products are born from executive planning and strategy meetings, where they develop a strategic plan that sets the direction of the company for the next 3-5 years. From this, they direct the VP of Product to develop a digital product and work with the Project Management Office (PMO) to get funding.

The VP of Product creates the initial product team, and finds a permanent space in the building where the product team can meet and collaborate daily.

Beyond that, the VP will provide on-going guidance in reviewing & approving the product strategy, business case, and roadmap.


title - product manager

The Product Manager has a lot of responsibility in shaping the future direction of a digital product, where they develop these key deliverables:

  • Product vision & strategy
  • Business case
  • Key product indicators (KPI’s)
  • Product roadmap

I always start by creating a Product Vision to help solidify the high-level assumptions of the product with the VP while providing guidance for the Strategic Product Planning process. To do this, just fill out the template below.

img - product vision

Next, I usually proceed by viewing all of the deliverables holistically by answering the following set of questions (see below), and then develop it as a single Product Strategy document since they’re all closely integrated.

  • What specific problem will our product solve? (value proposition)
  • Who are we solving the problem for? (target market)
  • How big is the opportunity? (market size)
  • What competitors currently exist? (competitive landscape)
  • Why are we best suited to pursue this? (our differentiator)
  • Why should we build it now? (market window)
  • How will we get this product to market? (go-to-market strategy)
  • How will we measure success/make money from this product? (metrics/revenue strategy)
  • What factors are critical to success? (solution requirements)
  • Given the above, what’s the recommendation? (go or no-go)

To accomplish this, the Product Manager will need to validate the initial assumptions by researching their competitors (if any), target audiences, and various technologies that could be utilized in the product.

Once the Product Vision & Strategy, Business Case, and KPI’s are finalized, the Product Manager will layout the Product Roadmap that outlines the goals, milestones, and deliverables for the product. For stakeholders, it’s typically laid out in a Gantt chart (see below) for as far out as you can plan for, but a minimum of 6-9 months.

img - product roadmap

For your product team, you may want to create a more detailed view (see below).

img - product roadmap detailed

The roadmap will be shared and updated often, so I recommend using an interactive roadmap product or template to simplify the process.


title - design lead

The Design Lead assists the Product Manager in developing the Product Strategy, and then starts developing the following deliverables.


Create the UX Vision & Strategy
The UX Vision captures the critical elements of the user experience and articulates the vision by focusing on the experience and downplaying the technology required to get there. The Design Lead will create the UX Vision by answering these targeted questions:

  • What type of user experience do you want your customers or users to have?
  • How will it support them in achieving their goals?
  • How will it help your company to achieve its goals and build your brand?

The Design Lead then creates the UX Strategy, which provides a roadmap to developing a product or service that an entire enterprise can rally around and work to achieve. It’s important because it ensures that all user touchpoints positively reinforce the brand and the user experience, resulting in a more cohesive and coherent product and customer relationship. View my post to learn the specific steps to creating the UX Vision & Strategy.


Establish the Design Principles
Design Principles are first principles that guide each design decision you make as you’re working on a product, and provides the necessary focus to create a kickass aesthetic and experience that’s consistent throughout the product that your users will absolutely love. These principles will encompass all design activities, from user experience design to visual design to interaction design; however, you can create separate principles for one or more design areas if you don’t believe the design principles are specific enough to a certain area.

img - design principles airbnb

To get started, review the Product Vision & Strategy, UX Vision & Strategy, and target audiences to reveal the characteristics of the product that will drive the design, seeking answers to these questions:

  • What are the primary needs of your users? Any special needs?
  • What types of products do your users currently use? Are there any design principles that you can pull from those products that would fit well with your product?
  • What are the typical physical, social, and technological environments that your users will utilize your product? How does design inform those environments?
  • What type of information does your product display? Is it one type or different types (e.g. photos, financial, technical, news, historical, etc.)? And how much data needs to be displayed?
  • Does your product encourage certain behaviors (e.g. sharing updates, buying goods, taking notes, etc.)?


Read more about the benefits of Design Principles, and also review these awesome examples of design principles from Apple, Paypal, and Airbnb if you’re still in need of inspiration.


Design the Design Tile
The Design Lead will then translate the Product & UX Visions into a visual design abstraction. I prefer using a Style Tile, which references interface elements like fontography, photography, color swatches, iconography, and patterns. If available, you can also include branding, site map, wireframes, and other user experience artifacts. Take a look at a few of my examples below.

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title - dev lead

Development Leads are responsible for assisting the Product Manager in developing the Product Strategy, where they need to review the various technologies on the market – as well as emerging technologies – that could be utilized to build the digital product.


Product Architecture
Once the Dev Lead has a solid idea of the product and various technologies available, they’ll create the Product Architecture utilizing minimal design while developing a flexible enough framework so that refactoring is easy.


System Design Documentation
A key deliverable is the development of System Design Documentation, which includes the following:

  • Solution Overview & Details – Services, Modules, Functional components & their responsibilities, Messages flows, Exceptions & related flows
  • Technical Architecture
  • Design Decisions
  • Requirements Artifacts – Business rule definitions, Use cases, Essential user interface prototypes, etc.
  • Solution Diagrams – Class diagram, Data model & entity relationship diagrams, Sequence diagram, Integration diagrams (Inbound/Outbound communication), Deployment diagrams (networking view)

The documentation should be lightweight, where you only document definitive decisions made, knowing that the system may evolve over time along with this documentation.


Setup Development Environments
Next, the Dev Lead will setup the development environments (dev, staging/test, and production) that the development team will need to successfully develop and deploy code starting in Sprint 1 (or even Sprint 0).



Now that you’ve completed these activities and deliverables, what’s next? It depends, but I typically recommend implementing a Sprint 0 to continue preparing your team for Sprint 1.

img - agile development phases sprint 0


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