Best Practices for Iterating on Project Roadmaps

Your product roadmap shouldn’t be a wish list. It should be a list of hypotheses you’re ready to be wrong about. If you’re not ready to be wrong, you’re not actually ready to prioritize. When you build your roadmap, focus on the outcome you want. For instance, you might say, “We believe Feature X will reduce churn by 10%. We’ll test that for the next two sprints.” That way, you’re tying the feature directly to a measurable result. If it doesn’t work, cut your losses and move on. If it does work, double down. This approach keeps you honest. You stop building features because they “feel right” or because someone on the team has a pet idea. You build them because you have a hypothesis about how they’ll change user behavior, and you’re open to seeing that hypothesis fail. Being wrong is an essential part of finding out what’s actually going to drive the metrics you care about. Here’s a quick example. Maybe you think adding a trial signup link to your pricing page will increase free trials by 20%. That’s your hypothesis. You put it on the roadmap, implement it, then measure the results. If you only see a 5% lift, you’ve learned something. Adjust the page again or try a new tactic. Either way, you’re making decisions based on real data, not gut feel. Another example: you might hypothesize that a chatbot in your onboarding flow will cut support tickets by 30%. Implement it, test it, and see if you’re right or wrong. If you’re wrong, you’ve still learned something about user preferences. That knowledge is gold. You can use it to decide what to build or not build next. By treating your roadmap like a series of experiments, you’ll move faster and waste less time. You’ll also build trust with your team and stakeholders because they’ll see exactly why each idea is there: it’s a hypothesis you’re willing to test. Remember, you don’t want to defend projects because you’ve already sunk time into them. You want to move on if the data says it’s time to move on. Keep your roadmap grounded in reality, always driven by an underlying guess about what will drive real impact. It forces you to put a stake in the ground about what you believe and to be ready to change course when you find out you’re wrong. That’s the whole point: you’re building a product for real people in the real world, and real data trumps wishful thinking every time.

At emdash, we recently shipped 3 major features in 3 months using a simple, 3-step planning process. Planning isn’t just about setting goals. It’s about assessing, learning, and adjusting based on what’s working – and what’s not. It’s about staying agile and primed to tackle whatever comes your way. Our 3-step process, inspired by Richard Rumelt's strategy work, keeps us aligned and focused. Here’s how it works: 1️/ Start with the Facts We begin by grounding ourselves in reality. Before jumping into new ideas, we take a step back and look at the current state. What’s going well? What’s falling short? This phase is all about clarity and alignment. We gather data – such as user engagement stats, customer feedback, and "dogfood" metrics – to paint an objective picture of our product and business. The goal is simple: ensure everyone on the team is on the same page about the challenges and opportunities. Example: If our usage data shows high churn in a specific customer segment, we focus on understanding the underlying causes. Are there key pain points? What insights can our customer success activities provide? 2️/ Develop Hypotheses Next, we craft hypotheses to explain these realities, striving to uncover root causes without jumping straight to solutions. This high-level thinking keeps us flexible and open to different possible solutions. Example: Based on the churn issue, we might hypothesize: "Customers in segment X are facing onboarding friction due to expectations set by using solution Z." This sets up the next step where we develop a plan to test the hypothesis. 3️/ Define Specific Actions Finally, we translate our hypotheses into concrete actions. This phase is where the roadmap takes shape, framed as a series of tasks to validate (or disprove) our ideas. Sometimes, this requires cutting an active workstream that no longer fits our evolving plan – a tough decision, but necessary to keep us disciplined and moving forward in the right direction. Example: If onboarding friction is the issue, actions could include redesigning the flow, conducting user interviews, or creating more educational resources for that segment with a specific nod to existing solution Z. Why This Works This 3-step process is collaborative, clear, and adaptable to any challenge the team is facing. It doesn't just tell the team what to do – it empowers them with a deep understanding of *why* each action matters. This leads to faster execution, better results, and a more cohesive team dynamic. Crucially, this approach also frees the team to develop even better solutions once on the ground during execution. How do you approach planning? Please share your strategies!

Should we kill the product roadmap? Roadmaps aren't the problem. It's the approach. Nokia learned this the hard way. In the early 2000s, Nokia dominated mobile phones. Their roadmap focused on hardware improvements, ignoring software. Meanwhile, Apple and Google disrupted the market with app-driven ecosystems. Nokia stuck to their plan and missed the shift. By the time they tried to adapt, it was too late. The iPhone and Android had taken over. 💡 Lesson: A static roadmap leads to irrelevance. Tesla, on the other hand, shows how to do it right. Tesla’s roadmaps are ambitious but adaptable. Not a fixed contract, but dynamic. They set goals like self-driving cars and Cybertruck timelines but constantly adjust based on real-world progress. Critics may call out Tesla for over-promising... But their ability to adapt to new business and market realities keeps them ahead. 💡 Lesson: Adaptability to market forces wins. Better to be late with the right product than on time with the wrong one. Here's the difference in the mentality: ❌ Bad Roadmap Thinking: "We promised X feature by Q3, so we must ship it, even if it's not fully ready." ✅ Better Roadmap Thinking: "We aim to improve user retention by 15% in Q3. What's the best way to achieve that, given what we’ve learned?" This is called adaptive roadmap thinking. Best Practices for Adaptive Roadmaps: 1. Communicate in Terms of Outcomes: Instead of "We will launch Feature X,” say, “Launching features X has a goal of improving conversion by 20%." 2. Implement Rolling Roadmaps: Update roadmaps regularly (eg, quarterly), allowing everyone to pivot based on new insights. 3. Openly Disclose Roadmap Uncertainty: Use language like “tentative”, “proposed”, "targeted", and "subject to change" instead of hard deadlines. 4. Establish Fast Feedback Loops: Implement processes for continuous customer insights, regular roadmap check-ins, and request intake and triage. The issue isn’t the roadmap itself... But treating it like a rigid plan. The best product managers continuously REWRITE their roadmaps. Rather than eliminating roadmaps entirely, high-performing product managers treat them as navigational tools, not contracts. Their roadmaps guide direction, not dictate destination. Product Managers that embrace adaptability - not certainty - will build the products that truly matter. If you're ready to rewrite your roadmap, grab my free Roadmap Health Check Assessment here: https://lnkd.in/erNUu4XB Kill the Roadmap? Or redefine it? ~~~ 👍 Like this post. ♻️ Repost this to your network. ➕ Follow Shardul Mehta to become a better PM. ✅ Subscribe to https://lnkd.in/eTMfsf-F