Let me tell you, the journey from a nascent idea to the app gracing your phone screen was anything but a straight line. It was a winding path, paved with lessons learned and fueled by a desire to solve a very real problem.
The Accidental Architect
Let's go back in time about a decade. Picture this: I was a seasoned Software Engineer, venturing into the uncharted territory of Product Management at a buzzing startup. Just a month into this new role, BAM! I was tasked with creating their very first product roadmap. Talk about a trial by fire!
I felt like an explorer dropped into a new continent with a compass that spun wildly. I barely knew the company's inner workings, the product was still a puzzle to me, and the market? A complete enigma. Standing in front of the executive team, ready to declare "This way, everyone!" felt less like leadership and more like a blindfolded guess.
But as they say, the title comes with the territory, ready or not. And "roadmap creator" was now firmly etched on my business card.
Navigating the Roadmap Minefield
Creating this roadmap felt like navigating a minefield blindfolded. Several thorny problems loomed large:
- The Knowledge Void: I simply didn't possess the deep understanding required to chart a confident course for a product I was still learning, within an industry I was still grasping.
- The Capacity Conundrum: Even if I did magically conjure a brilliant roadmap, I had no real grasp on when these features could actually be built. Our lean engineering team was already wrestling with a backlog of promises made in exchange for crucial early sales.
- The Timing Tangle: The request was clear: a roadmap stretching into Q1, Q2, Q3, and beyond. But with our limited capacity and fuzzy understanding of feature scope, any attempt at precise timelines felt like pure guesswork.
The Data-Driven Revelation
Faced with this daunting challenge, I knew I had to find a smarter way. I might not have all the answers myself, but I was surrounded by people who held pieces of the puzzle. The catch? Navigating the internal landscape felt like a political tightrope walk. Each of the three primary stakeholders held strong opinions, often contradictory. Get any one of them alone, and you'd hear tales of the others' misjudgments. But dare to challenge their individual ideas in a group setting? Suddenly, they'd unite into a formidable, single voice. Getting consistent direction felt like trying to herd cats during a thunderstorm.
That's when the lightbulb flickered on. If I couldn't rely solely on subjective opinions, I'd turn to cold, hard data. I decided to create a system that would weigh the expertise of each stakeholder, each department, and let the collective wisdom rise to the surface.
The Power of the People (and Numbers)
My first move? A survey. I meticulously listed every feature on the table, including those already promised to early adopters. This wasn't just for internal folks; I also reached out to a select group of strategic customers – the ones who held the potential to truly make or break us.
The survey was simple yet powerful: rank these features. What excites you the most? What's less important? What feels completely irrelevant?
As the responses trickled in, I wasn't just tallying votes. I was meticulously noting the department of each employee respondent and the hierarchical position of each stakeholder. For our valued customers, I noted their industry and size.
Then came the crucial step of understanding the "why" behind the "what." I gathered the CEO, COO, CTO, Head of Sales, and Head of Customer Success for a focused discussion. I presented them with four key categories: Revenue and Retention (the "growth" drivers) and Effort and Time (the "cost" factors). After a spirited couple of hours of negotiation, we arrived at a ranked order for these crucial business drivers.
The SQL Sorcery
With the raw data in hand, I dove into my engineering comfort zone: a database. I meticulously entered every survey response, every employee, and every customer. Then came the magic of weighting.
Each employee was assigned a weight based on their level (C-Level, stakeholder, employee) and their department. They received higher weights for the categories where their expertise naturally lay. I even factored in their industry knowledge based on years of experience.
Similarly, each customer was weighted based on their alignment with our target market and their size.
Finally, the moment of truth. I crafted a SQL query – a digital alchemist's formula – that combined all the weights and rankings to generate a score for each feature. And just like that, a stack-ranked list emerged, revealing the features that held the most potential to propel the company forward.
The Great Capacity Reckoning
With a data-backed roadmap in hand, the next hurdle was the stark reality of our limited engineering capacity. We had promises to keep, features "owed" to early believers. But we knew that clinging to these individual commitments at the expense of the overall strategic direction was a recipe for stagnation.
It was time for a brave, albeit potentially uncomfortable, conversation. We decided to communicate transparently with each customer, explaining that if their "paid for" feature didn't align with the near-term roadmap, its delivery would be delayed – potentially significantly. If a customer chose to leave because of this, we would apologize and move forward, resolute in our commitment to the data-driven path.
Let me tell you, the fear of losing those early customers was real. But guess what? Zero. Not a single one left. They had found value in the product in so many other ways, and in some cases, their initial need had even evolved.
Trading strategic growth for individual feature requests is a dangerous game. It's essentially letting a small handful of customers dictate your future, regardless of market shifts or new opportunities. Don't fall into that trap.
The Art of the "Now, Next, Later"
The final piece of the puzzle was timing. How could we accurately predict delivery timelines for features we didn't even have detailed requirements for? We risked significant misjudgments in scope and, therefore, delivery dates.
That's when I stumbled upon a game-changing idea, courtesy of the Foursquare Product Manager (remember the check-in app?). They advocated for ditching rigid, period-based roadmaps in favor of a simpler, more agile "Now, Next, Later" framework.
The concept was brilliant: identify the number of features your team can realistically tackle Now and pull them from the top of your prioritized list. Next holds the subsequent set of features. Everything else? It goes into the Later bucket, acknowledged but not actively worked on and subject to change as new information emerges.
Engineers focus on Now, Product Managers refine Next. Nobody gets bogged down in the distant Later. By the time those Later items approach, you'll likely have a fresh perspective and potentially a revised roadmap.
The beauty of this approach? Everyone focuses on what truly matters: the immediate priorities. The rest is noise, a source of unnecessary stress. Those tasks will have their moment; until then, let them be.
Prioritize Me: The Seed of an Idea
But I thought, if I'm going to build a to-do list in my spare time, why not build one that manages my tasks the way I managed our product roadmap? With data!
The initial concept, which I called "Prioritize Me," was simpler. You'd enter your tasks, rate their importance, urgency, whether they were for yourself or others, and hit submit. Behind the scenes, these tasks were dropped into a hidden list that used the Eisenhower Matrix to calculate a score.
Your dashboard was minimalist: a button that asked "What's Next?" and a list of tasks you were currently "In Progress" on. When you needed your next task, you'd hit that button and be presented with tasks one at a time, in order of their score, until one resonated. Click "Start," and it moved to your "In Progress" list.
It was functional, but it lived only on the web. Mobile app development was a skill I hadn't yet acquired, and time was a precious commodity. By 2021, even I had stopped using Prioritize Me. It lacked crucial elements: reminders, more nuanced scoring, the ability to group tasks into lists, and a way to tie tasks to larger goals (I've been a bucket list enthusiast since way before "bucket list" was a buzzword!). Plus, the enterprise-grade cloud hosting I'd chosen was proving ridiculously expensive, even for just myself.
Enter Whenable: The Evolution
And that's where Whenable truly began to take shape. It was an 18-month labor of love, squeezed into evenings and weekends around a full-time job and cherished family time. Learning to build mobile apps for two platforms was a significant undertaking.
But this time, I had a vision. If I was going to build it, it would be the to-do list I always wanted. It would be my one and only, encompassing everything I needed. Once it was ready, I'd share it with the world. But first, I'd build it on a cost-effective cloud platform, ensuring its longevity even if I remained its sole user.
The day I first released Whenable in closed beta, my cloud bill was less than a monthly subscription to established apps like Todoist or TickTick. A resounding win!
I've been using Whenable since those early beta days, and it has become an indispensable part of my life. The performance stats constantly motivate me to improve it. I rely on the AI to handle the scoring, freeing up my mental energy. And even the most daunting tasks feel manageable with Whenable AI providing step-by-step guidance.
TL;DR: Your Personal Product Manager in Your Pocket
So, where did Whenable come from? It wasn't a whimsical notion. It was born from the real-world challenges of building a strategic roadmap in a chaotic environment. It's the distillation of those lessons learned, applied to the seemingly simple task of managing your personal to-do list.
To me, Whenable embodies how professional Product Managers approach building a roadmap for their company, with its very growth and future hanging in the balance. Only in this case, those diligent "Product Managers" live right in your pocket, tirelessly working on your personal growth and success.
