Career Roadmap Creation

Your 2025 Product Roadmap will fail (And That's OK) - Here's the real way to plan After over 8 years in Product, here's what no one tells you about roadmap planning: 1. Start with problems, not solutions: Instead of: "We'll build feature X in Q1" Write: "We'll solve user problem Y, current impact: $2M lost revenue" The hard truth? 80% of PMs start with solutions. Then wonder why their roadmaps fail. 2. Kill your darlings: - That exciting AI feature everyone's pushing for? Maybe it's just FOMO - The enterprise feature your biggest client wants? Could be a distraction - The technical debt your team's been ignoring? Probably your real Q1 priority 3. Reality check your timeline: - Take your engineering estimate. Double it. - Take your expected impact. Cut it in half. - Now you're getting closer to reality. 4. The 40-40-20 rule I live by: - 40% for planned strategic initiatives - 40% for unexpected opportunities/fires - 20% for innovation and tech debt Most PMs do 80-20-0. Then burn out their teams. The hidden cost no one talks about: Context switching kills 20% of your team's capacity. That's why spreading your roadmap too thin is actually slowing you down. 5. The stakeholder game: Different stakeholders need different views: - Engineers need technical feasibility - Executives want business outcomes - Sales needs timeline confidence Most PMs create one roadmap for everyone. That's why they fail at alignment. 6. The monthly reality check: Set a calendar reminder for the first Monday of every month: - What did we learn last month? - Which assumptions were wrong? - What market changes are we ignoring? - Which dependencies are at risk? Your roadmap isn't a commitment. It's a hypothesis waiting to be proven wrong. The best PMs in 2025 won't be those who: - Ship the most features - Never miss deadlines - Always say yes to stakeholders They'll be those who: - Adapt fastest to reality - Say no with confidence - Keep their teams focused when everything is on fire Remember: A roadmap is a tool for alignment, not a prison sentence. What's your process for planning a roadmap?

Roadmaps are not one-size-fits-all. They should be tailored to each team. Why? Because roadmaps aren’t just timelines, they’re communication tools. And what you communicate depends on your audience. Consider these examples: - Product Development Teams need detailed, execution-focused roadmaps. Think engineering commitments by quarter, discovery vs. delivery status, and alignment on what’s coming next. - Sales Teams are looking for big-picture stories. They need to know which features will excite customers and when they might expect them. These roadmaps focus on value propositions rather than granular details. - Leadership needs a strategic view. Roadmaps for them focus on initiatives and capacity planning, linking back to the company's broader vision and goals. To create all these roadmap versions effectively, we need collaboration between product operations and product teams. That way, each roadmap serves its specific purpose and audience. Take Rebecca’s example from my Product Operations book with Denise Tilles. By keeping these roadmaps aligned with business rationale, she was able to bridge the gap between sales expectations and product realities, building trust and transparency across the organization. She also introduced a clear framework for sharing feature status across teams. This included stages like Discovery, Alpha, Beta, and GA. Understanding these phases ensures that everyone, from sales to engineering, knows the real status of a product feature and can communicate that clearly to customers. The magic happens when product operations steps up to support these efforts. By providing tools and frameworks, ProductOps help teams to align their roadmaps with strategic intents and prevent the kind of overselling that happens when teams aren’t on the same page. In short, roadmaps aren't just plans, they’re how you build alignment. How are you tailoring roadmaps for different departments in your organization? Let me know in the comments!

“This roadmap is useless.” The words hit like a gut punch. After weeks of alignment, dependencies mapped, and every detail airtight… it fell flat in front of leadership. ❌ Too many details. ❌ No clear business impact. ❌ Buried in feature updates. That’s when I learned the hard way—one roadmap doesn’t work for everyone. One roadmap for all? Like sending the same email to your CEO, engineers, and customers—it won’t land. Each group needs different information, framed for their decisions. Here’s how to tailor your roadmap for success: 1️⃣ The Strategic Roadmap (For Executives) Audience: CEOs, leadership, investors Focus: Business outcomes, long-term vision, and key initiatives ✅ How to get it right: -> Keep it high-level—focus on themes, not feature lists. -> Tie initiatives directly to business goals and revenue impact. -> Use concise visuals (timelines, OKRs, measurable impact). 💡 Pro Tip: Your execs don’t need sprint details—just the “why” and how it moves the business forward. 2️⃣ The Tactical Roadmap (For Engineering) Audience: Product & engineering teams Focus: Priorities, dependencies, technical feasibility ✅ How to get it right: -> Provide clarity on scope, timelines, and trade-offs. -> Show how engineering efforts ladder up to business goals. -> Address dependencies upfront to avoid last-minute surprises. 💡 Pro Tip: Engineers don’t just want deadlines—they need the "why" behind decisions to make smarter trade-offs. 3️⃣ The Narrative Roadmap (For Customers) Audience: Users, customers, prospects Focus: Features, value, what’s coming next ✅ How to get it right: -> Focus on pain points solved, not just new features. -> Use visuals like wireframes, mockups, or sneak peeks. -> Be transparent—set clear expectations on timelines. 💡 Pro Tip: Customers don’t care about your internal priorities—they just want to know how you’re making their lives better. — 👋 I’m Ron Yang, a product leader and advisor. Follow me for insights on product strategy + leadership.

Nobody tells you this about product management… Your first 30 days? There’s no structured onboarding. No neat checklist. No “here’s how things work” walkthrough. Most times, when you’re new, you’re tossed in the deep end and expected to paddle. Fast. Welcome to the deep end. That’s where you start in product. And that’s where I am right now - navigating a new product initiative. The product has existed for years but needs a full-scale revamp. To say it’s complex would be an understatement. Everything is hard to decipher. No clear boundaries. It’s bigger than anything I’ve ever worked on. But I hold onto one core belief: To shape the future, you have to understand the present. This belief is how I build clarity out of confusion and ramp up, project after project. Here’s what I do: 🟣 Step 1 - Map the People > Action: Identify everyone on the core product team. Product managers, lead developers, program managers, designers. > Deliverable: Org Chart - create a visual that shows key players, roles and team structures. 🟣 Step 2 - Know the Sponsors > Action: Find out who funds the initiative and who cares about the outcome. > Deliverable: Stakeholder Map - categorized by influence, interest and involvement. 🟣 Step 3 - Understand the Problems > Action: Define customer pain points and their impacts on the business. > Deliverable: Problem x Impact Matrix - context pain points to business goals, OKRs and KPIs 🟣 Step 4 - Explore the Product > Action: Go into discovery mode and use the product like a new user. Poke around. Try breaking something. Take notes. > Deliverable: Usability Log - what works, what’s clunky, questions that you have. 🟣 Step 5 - Review the Roadmap > Action: Discover what is currently on the product roadmap. What does the team plan to deliver this year and why? > Deliverable: Annotated Roadmap - key features or capabilities linked to problems and opportunities in Step 3. 🟣 Step 6 - Ask about the Vision > Action: Ask leadership and teams on the product’s future state. > Deliverable: Vision Snapshot - a one-pager comparing where we are today with where we want to be. 🟣 Step 7 - Synthesize Your Findings > Action: Bring everything together. > Deliverable: Observation Breakdown that includes challenges, questions, opportunities, gap analysis (now versus future) and quick wins va long-term efforts. 🟣 Step 8 - Prioritize with Your Team > Action: Align with product, design, engineering and leadership on where you should focus. > Deliverable: Ramp Up Action Plan - a short term execution plan that goes after the prioritized work. At the end of this process I walk away with a clearer sense of the chaos. This becomes my foundation for everything else that is built out in planning, pitching, developing and shipping. PM is ambiguity at its best (and worse). You need an approach to navigate it when ramping up. This is mine. What is yours? #productmanagement #productmanager

In RevOps, if you don't own your roadmap, someone else will; on small teams, managing one is sometimes more complicated than not having one, but the effort is worth it. 🚫 Without a roadmap: - Generally, the loudest voice in the room decides what you focus on, - Your team becomes reactive and burns out, - Resources are drained away from projects that drive revenue, - The "must do" projects become "might do" projects, - Quality slips, - You lose a strategic voice in go-to-market decisions, and - Changes are not successfully adopted ✅ With a roadmap: - The loudest voice now has to "give-get", - Reactive projects are submitted as tickets and prioritized against priorities, - The team has better visibility into their current and upcoming workload, - Resources can be allocated to revenue drivers first, everything else second, - Projects can be scoped, designed, and implemented in phases, - You buy time to run quality assurance testing, - Impact, resource, and time are considered with go-to-market decisions, - The team can adequately train and rollout changes I've learned and continue to learn that you don't have to have anything fancy to have a roadmap; in fact, simpler is usually better. Here's what has worked for me: 🧠 Do a brain dump with your team ⭐ Group everything into two buckets: "Reactive" and "Proactive" 👑 Rank every item based on its ability to impact revenue, "High", "Medium", and "Low" ⏲️ Assign an estimated amount of time to complete each item (remember to allocate time to design, build, test, and train where necessary) 🥇 Priorizte High Impact, Proactive, Fast to Low Impact, Reactive, Time Consuming 👩⚖️ Get sign-off with leadership to make sure everyone understands and agrees with the prioritization 🚧 Start a sprint and get going! Remember, the smaller the team, the more difficult this can be. Sometimes, a team of one can keep a to-do list in its head better than a team of ten. So write it down and share it out so you own your roadmap! #revops #salesforce #mops #startup #revenueoperations #salesops #marketingops #roadmap #sprintplanning #friendsofyeti

Product planning is better approached like a game of Pokémon - not Tetris. In Tetris, you’re just stacking blocks, hoping they fit before you run out of space. But in Pokémon, every stage is an evolution - each phase builds on the last, growing stronger and ready for bigger challenges. So why limit your roadmap to “small, medium, large” when you can plan for evolution instead? With "crawl, walk, run" planning, you don’t just categorize initiatives by size; you guide them through stages of growth. You start small, test assumptions, then ramp up commitment based on what you learn. Like training a Pokémon, each phase has a purpose, each investment has a direction. It’s dynamic, adaptable, and strategic. Here's how I think about the three phases of evolution: 1️⃣ Crawl / Charmander: Small, low-risk projects that test core assumptions. At this stage, you’re just placing a bet, seeing if the idea has legs (or wings!). 2️⃣ Walk / Charmeleon: When a project shows promise, it “evolves” into a Charmeleon. Now, it gets more resources and a refined strategy, moving beyond the basics to make a bigger impact. 3️⃣ Run / Charizard: The final evolution. Here, you go all-in, investing heavily to maximize results and push the vision forward. You're flying. This approach doesn't just sort projects by size; it gives them a journey. Tetris blocks just stack up and disappear, but Pokémon evolve—and so can your roadmap. With phase-based planning, you can adapt as you go, double down on your strongest bets, and watch each phase build into something way more powerful.

Friday thought: Roadmap prioritization is both art and science. After building products for more than a decade, for all kinds of companies, the priority order for roadmap initiatives ends up roughly as: 1. Projects that have a clear path to increased ARR: If you have a (fast) path to building something that people find dollar value, these always win out. 2. Projects that retain existing customers, in ARR order: Next, you are reducing anticipated churn based on a large common ask from companies by some average of ARR. People typically run into a trap of constantly responding to support requests, which is not the same. Here, we identify strategic projects that would average out in a better experience for a wide variety of customers, not the loudest one. If you build for the loudest one, even if they have a lot of money, they probably are going to leave you anyway (and often times, it isn't your fault). After these, you have a tie between: -- Projects that lead to greater efficiencies or saving money: To protect the bottom line, you have to use your resources wisely. Whatever you can do to help save a few bucks on the AWS bill or get work done twice as fast can help pay dividends that can support 1 & 2. Sometimes people lump "tech debt" projects in here, but you'll want to be judicious about time boxing these projects so teams don't over-rotate here. -- "Spike" initiatives that may lead to future business directions or open up new channels: Whereas with the above efforts the vision and end state is clear, there are often large areas of opportunity that are worth the risk to investigate. A lot of "AI" based ideas can fall in this bucket - there are other ways to solve problems that are more obvious, but perhaps a new technology can unlock new ways of working that were previously impossible. Deciding between the above depends on the lifecycle of the project or business. If the company is more mature, they may do more things to reduce cost. If you are just getting started, exploratory intiatives take more priority.

The Minimum Viable Process to Run a Team Most of my team members come from Amazon, Google, Meta, or Microsoft. Since we are still in the early stages of building the team, we faced an exciting challenge: although we have a talented and diverse group, we also bring together different engineering cultures, each with its own approach. The key question was: what is the simplest process we can adopt to harness our collective potential toward a common goal, instead of allowing it to diverge in multiple directions? Engineers tend to dislike processes by nature, but technically, no process is inherently a process. The famous maxim "don’t be evil” is effective because it depends on a common, unspoken understanding of what constitutes evil. The aim wasn't to eliminate all processes, but to identify the right type—those that serve as supportive tools for the team instead of restrictive barriers. The process we adopted is as follows: First, we need a directional roadmap. This isn't a detailed project plan but a series of broad sketches outlining major goals for each quarter. Since predicting the exact future two quarters ahead is impossible, our roadmap embraces deliberate ambiguity. It acts as a strategic compass rather than a precise GPS. It helps us stay aligned as we navigate unforeseen challenges daily, anchoring us with the core 'why’ behind our work. Second, we need a way to turn the roadmap's vision into clear, actionable projects. This acts as the bridge from strategy to execution. We intentionally keep project plans separate from technical design. The project plan emphasizes what needs to be done and when—highlighting the incremental value delivered to customers or stakeholders. The technical design focuses on how, allowing our engineers the freedom to apply their expertise and creativity. This separation ensures we can make reliable commitments while empowering our engineers to determine the best approach. Finally, we hold weekly check-ins to reflect on progress and plan ahead. This rhythm is our feedback loop, ensuring we stay on track or adjust as needed. It also serves as a forum for addressing ad hoc issues and crises that could disrupt work. As Dwight D. Eisenhower said, “A Plan is nothing, planning is everything.” To support this rhythm, we use a simple Kanban board that offers a shared, transparent view of project statuses. However, a Google Doc with a basic structure can work just as well. The format isn’t very important. For external stakeholders, this extends to a biweekly update—a straightforward summary of project status indicators (green, yellow, red), completed tasks, ongoing work, and upcoming plans—helping build trust and manage expectations with minimal effort from our team. This is it—a roadmap that transforms into projects for execution and establishes a weekly rhythm for feedback. When you gather a team of experts, your main task isn’t to manage them but to create a shared context that allows them to manage themselves.

If you’re a product manager at a startup or small company, chances are you’re wearing multiple hats. 🎩 You’re not just the PM handling the tactical details—you’re also covering the responsibilities of a Head of Product or VP of Product. If you’re juggling three distinct levels of roadmaps: goals, product, and features. Let’s break these down: 1. The Goals Roadmap 🎯 This is the big-picture, strategic layer. It defines the business and product goals that guide everything else. Think of it as your North Star. Example: “This quarter, we’re improving customer retention by 10%.” If you’re at a startup without a VP or Head of Product, this responsibility often falls to you. You’ll need to connect company objectives to actionable goals and communicate them effectively. 2. The Product Roadmap 🗺️ Sitting in the middle, the product roadmap focuses on initiatives—the “what” behind achieving your goals. Example: To hit that retention goal, you might prioritize launching a loyalty rewards system or revamping onboarding. This roadmap translates high-level objectives into tangible projects, aligning your team and stakeholders around the journey. 3. The Feature Roadmap 🔧 This is your tactical layer. It deals with the specific features and deliverables needed to execute the product roadmap. Example: What exactly needs to be built for the loyalty rewards system? A dashboard, notifications, and user account features? Here, you’re moving from strategy into detailed planning, ensuring the team has clarity on what to build and when. How This Differs in Bigger Companies 🏢 At larger companies, these three layers are often split across different roles: • VP of Product/Head of Product handles the goals roadmap and sets overarching priorities. • PMs focus on the product roadmap, deciding what initiatives to prioritize to meet those goals. • Team leads, or engineers often drive the execution of feature roadmaps, managing backlogs and specific deliverables. As a PM in a larger organization, you’ll usually focus on two layers: 1. Strategic Initiatives (connecting goals to product direction). 2. Tactical Execution (turning initiatives into backlog items). Why This Matters 💡 Understanding these layers—and who owns them—is crucial to navigating your role: • At startups, owning all three layers gives you a holistic view and ensures alignment across goals, product initiatives, and features. • In bigger companies, knowing where you fit helps you stay focused while collaborating effectively with leadership and delivery teams. Whether you’re at a small company or a large one, clarity around these roadmaps ensures you’re always driving the right priorities. ✅

🌊 A Captain. A Storm. A Roadmap. The ocean was unforgiving. Waves towered like skyscrapers. Winds screamed warnings no one wanted to hear. A seasoned captain stood at the helm, soaked, eyes locked on a horizon no longer visible. The ship—massive, prestigious, carrying hundreds of passengers—was losing direction. The map was outdated. Instruments failed. Crew members scrambled, reacting instead of navigating. The risk of total loss grew by the hour. Until something changed. The captain retreated for a moment—not to abandon the helm, but to create a new roadmap. One that wasn’t reactive but predictive. One that read the environment, understood the vessel’s strengths and weaknesses, and guided the crew back toward value, not just survival. ⸻ 🚢 That ship wasn’t a vessel at sea. It was a large financial organization. And the captain? Dr. Tony Prensa, a visionary PMO strategist. When this company found itself drowning in initiatives, projects without alignment, and leaders lacking clarity, Dr. Prensa didn’t reach for a one-size-fits-all solution. He built a bespoke PMO Roadmap—designed around the organization’s purpose, risks, culture, and strategy. Like a true navigator, he: • Assessed turbulent waters (organizational maturity and priorities) • Charted the currents (value streams and stakeholders) • Defined the destination (a value-driven, customer-centric PMO) • Equipped the crew (through governance, tools, and competencies) 🌟 The result? A turnaround that brought focus, agility, and trust. A PMO that not only survived the storm—but became the lighthouse. ⸻ 🔍 PMO leaders: Your roadmap is more than a plan. It’s a lifeline. Don’t wait for the storm to hit. Build your PMO roadmap like your organization’s life depends on it—because sometimes, it truly does. #PMO #ProjectManagement #Leadership #StrategyExecution #TonyPrensa #PMORoadmap #BusinessAgility #OrganizationalResilience