The “Rolling” Double Diamond Strategic Execution Process For Scaling Startups & Product Teams

Becky Flint
Responsive Product Portfolio Management
4 min readJan 21, 2019

by Becky Flint

January 21, 2019

Every company (or product line or business unit) needs to define and execute strategies to achieve its vision and goals. In my mentoring sessions with startup founders and budding engineering or product leaders, questions around Strategic Execution came up often, especially at the end or beginning of a year.

The goal of this post is to provide an overview about the Strategic Execution process, its key participants, and winning characteristics in each stage.

Strategic Execution is not about building individual product features.

Strategic Execution is about how the entire company (or business unit/ product line) decides on what problems to solve or opportunities to exploit in the next 2–6 months, and create and execute an operating plan for it. The operating plan includes set of product features, resourcing, and release plan.

It’s a (slightly) bigger picture process than the product feature design and build process.

A good strategic planning and execution practice follows a directional yet iterative process of agreeing on goals, defining strategy, creating plans, and executing them.

It is not a funnel because feedback from the “next” stage often requires adjustments to the prior stage. For example, if building a certain feature would consume most of the existing resources for the next 3 months, a different strategy such as integrating a 3rd party app can be incorporated to replace the previous strategy (build in house). Alternatively a different execution approach such as using an external agency may be adopted to replace previous execution approach of using current team and delaying other features. A 3rd option is breaking the feature into phases, in which case it changes both the previous strategy and execution approach.

In fact, this process can be roughly illustrated using the “Double Diamond Design Process” popularized by the UK Design Council.

“…a number of possible ideas are created (‘divergent thinking’) before refining and narrowing down to the best idea (‘convergent thinking’), and this can be represented by a diamond shape.. the Double Diamond indicates that this happens twice …

One of the greatest mistakes is to omit the left-hand diamond and end up solving the wrong problem..”

UK Design Council

During the Double-Diamond Strategic Execution Process, product managers (“PM”) and various participants converge in key inflection points to move from one stage (diamond) to another.

Circle 1: brainstorm and decide on what problems to solve
An example list of problems are: sign up conversion trending lower, UX issues from users (collected from customer support, website chat, social media, etc.), admin tool crashes, billing issues, new features needed to close deals to hit revenue numbers, new features demanded by marquee customers to keep them happy / not churn / add more users.

Circle 2: brainstorm and decide on how we will solve these problems (who/ which team to work on what features)
The key idea is not to solve only 1 type of problem, but to distribute time and resources in the best possible way. Continuing the example above: maybe the conversion issue is more urgent, but some are dependent / related to the UX issues. Promises to a new customer or marquee customers may come in later, there may be a workaround for the admin tool crashes or billing issues could be done by outsourced agencies. These factors will help sequence a plan for various teams.

Circle 3: build the features planned during Circle 2.
And of course as products are being built or even partially released, new discovery may pop up and a “trip back” to the earlier stage is needed, which means the rest of the plan may be checked once over to see whether changes there are warranted.

Due to the switch between Divergent Thinking and Convergent Thinking through the Strategic Execution process, the success of building the right products to solve the right problems requires alignment of product features, assessment of various options around timing and resourcing scenarios, as well as visibility to key participants.

Traditionally the Product Alignment, Roadmap Scenarios, and Visibility have been ensured through meetings, spreadsheets, and sheer hours of hard work.

With a right tool, you can align better, plan faster with better decision quality and effortless visibility.

Dragonboat is a purpose built Product Execution System for teams to build with confidence.

About the author: Becky Flint

Becky is a veteran product and program leader passionate about building products and teams. Before founding Dragonboat, Becky was VP of Product Programs at Feedzai, scaled its global product building as the company doubled in size. Prior to Feedzai, Becky was Founder and CEO of Scaffold Consulting, VP of Strategic Planning and Programs at Bigcommerce, and head of Product Programs of Tinyprints/ Shutterfly, and head of PMO for PayPal Global Payments and Credit.

Originally published at dragonboat.io on January 21, 2019.

Title image courtesy of Pixabay

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Becky Flint
Responsive Product Portfolio Management

CEO of dragonboat.io — The Product Operations Platform for product leaders to maximize impacts via effective product portfolio investments and delivery.