During my time at Crimson Hexagon, our UX design team introduced the Design Thinking process into our product development workflow, using it to structure the research phase for our new products and features. This approach proved transformative, helping us address complex user needs and stay agile in a shifting market.
When I later joined True Fit, we faced a pivotal moment where competitive pressures and market shifts called for a comprehensive roadmap overhaul. Recognizing the need to recalibrate our strategic vision, I turned to Design Thinking principles - especially focusing in on the “Define” stage - to articulate the most pressing problems we needed to solve as a business with a long term lens without simply anchoring on specific solutions the leadership team had most recently been evangelizing.
Here’s a closer look at how Design Thinking structured my approach to creating a cohesive strategic vision and a user-centered roadmap.
What Is Design Thinking?
For those unfamiliar, Design Thinking is a human-centered problem-solving approach which puts understanding user needs at its heart. It’s structured to challenge assumptions and refining solutions through iteration. This method unfolds across five stages:
- Empathize – Understand users’ needs through research, observation and engagement.
- Define – Articulate a clear problem statement based on insights from the empathy stage.
- Ideate – Generate a range of potential solutions without judgment.
- Prototype – Develop tangible models to test ideas with users.
- Test – Gather feedback, refine ideas based on insights and improve the solution.
This is a great framework to use to build out new products in a user-first, agile manner. I’ve found the first two stages and associated exercises, in particular, to be very helpful in grounding a cross-functional leadership team to gain a shared perspective on the opportunities and threats a business is facing, and to help outline high level strategy which can guide the building of strategic pillars, and ultimately an impactful multi-year roadmap.
Reframing Strategic Vision with Empathy and Problem Definition
A couple of years ago at True Fit, our team’s evolving understanding of the market underscored the need to rebuild our roadmap. We didn’t just need a new set of roadmap items or even a refresh on our strategic pillars, we needed to redefine our platform’s direction based on the core opportunities and problems to be solved we saw at the time in the marketplace for both B2B customers and B2C end consumers.
As a B2B2C company, our solutions serve both online retailers (e.g., real-time analytics and personalization data) and their shoppers (e.g., size recommendations and profile management). This dual focus required us to develop empathy for both segments at the same time, ensuring our roadmap addressed the needs of each.
The "How Might We" Brainstorming Exercise
The “Define” stage of Design Thinking includes an exercise called “How Might We” (HMW), which I had adapted in previous roles to create product-level visions. This exercise, which I applied at True Fit for our strategic visioning exercise, involves brainstorming with sticky notes (physical or virtual - I found mural.co to be a great virtual tool), where each team member frames potential user problems starting with “How might we…?” Examples include:
- HMW: Provide retailers real-time insights into recommendation performance?
- HMW: Offer shoppers better access to their saved profiles?
- HMW: Deliver generalized sizing advice for first-time users?
I convened a cross-functional team spanning UX Research, Customer Support, Data Science, Engineering, Sales, Marketing, B2B Integrations and company leadership. Together, we generated hundreds of sticky notes, each representing different user challenges and product ideas. Team members then shared their HMW statements, enabling others to see their perspectives. We then collaboratively organized all of these ideas into groups of similar concepts. This clustering distilled our ideas into 5–10 key themes, representing our collective ideas for where our product development team should place their focus going forward.
From Core Themes to Strategic Pillars
Once we identified our core themes, the team labeled each cluster and added concise descriptions which attempted to describe the underlying sets of ideas. Product leadership further refined these clusters into 3–5 strategic “pillars” which had the highest potential impact for the company evaluated against a matrix of factors. Each pillar represented a key area of focus, providing a perspective on key problems to be solved over any specific product ideas (leaving product ideation to a future roadmapping process where the executing team would be empowered to provide these ideas!)
The next step was synthesizing these pillars into one cohesive strategic vision. Here, a product leader’s role is to connect the pillars into a “North Star” statement - one overarching label that pulls together all of these pillars to reflect the company’s mission which can then provide direction and alignment across all teams within the company.
The Power of Inclusive Collaboration
Design Thinking’s Empathy and Define stages enabled us to develop a strategic vision and pillars grounded in empathy for our users. That vision and those strategic pillars led to a roadmap rooted in genuine user and market needs rather than a wishlist of features pushed top-down from leadership. By prioritizing real user problems, applying Design Thinking to your Strategic Visioning process can foster enhanced focus and team empowerment.
In addition to providing structure, Design Thinking’s collaborative nature supports cross-functional buy-in, helping all teams feel invested in the strategic vision as each team was able to take part in its creation.
Final Thoughts
Leveraging Design Thinking to create a strategic vision allows organizations to stay flexible while centering on user needs. The result is a strategic vision and roadmap that resonates with customers, users and other stakeholders and provides a mechanism for internal teams to stay aligned and deliver meaningful outcomes.