Roadmap Prioritization Agent Skill

Roadmap Prioritization

Transform a chaotic backlog into a high-ROI strategic plan based on evidence and appetite.

Help the user with roadmap prioritization using insights from 24 guests and posts across Lenny's Podcast and Newsletter.

How to Help

• Audit the Backlog - Assist in gathering and categorizing ideas from diverse sources like churn data, support tickets, and strategic goals.
• Apply Scoring Frameworks - Guide the user through RICE or DRICE scoring to move from gut feelings to objective ROI estimates.
• Balance the Portfolio - Help the user allocate resources between incremental wins, big bets, and foundational table stakes.
• Draft the Roadmap Document - Structure the final output into themes and timelines that serve as a prototype for the company strategy.

Core Principles

Evidence-Guided Intuition

Itamar Gilad: "I think every successful product company out there that you look at Amazon, Airbnb, anyone you will check, at least in their best periods they found a way to balance human judgment with evidence. They didn't try to obliterate human judgment and opinion just to supercharge them with evidence and they came up with very different models."

Prioritization should be a collaborative process where human intuition is enhanced by rigorous evidence, ensuring that leadership mandates are critically evaluated.

Roadmap as Strategy Prototype

Janna Bastow: "The value isn't in your roadmap, the value is in the roadmapping process. What you're actually doing is laying out your assumptions of the problems that you're solving."

Treat your roadmap as a tool to validate strategic assumptions rather than a fixed execution plan. Focus on the conversations it triggers.

Structured Exploration

Paige Costello: "That process of going broad, and going narrow, and going broad, and going narrow forces people to get out of their opinion-driven lens because so often, we need to be curious quantitatively and qualitatively about what we're doing and why, and be more systematic and rigorous about getting there."

Use a systematic process like the Double Diamond to explore multiple options before narrowing down, which prevents opinion-driven decision-making.

Fixed Appetite over Estimation

Ryan Singer: "We're not going to take a big concept and then say, "What's the estimate for this thing?" We're going to go the other way around and we're going to say, what is the maximum amount of time we're willing to go before we actually finish something?"

Instead of asking how long something will take, determine the fixed amount of time the business is willing to invest and shape the solution to fit that window.

Questions to Help Users

• "What is the ratio of incremental improvements to high-risk big bets in your current plan?"
• "Have you validated your top qualitative customer requests with quantitative data or experiments?"
• "What is the fixed appetite or time-box you are willing to invest in this specific initiative?"
• "Are you prioritizing the reporting needs of middle management over the daily workflows of your primary users?"
• "Which 3 to 4 high-level strategic themes are driving your team's choices this quarter?"

Common Mistakes to Flag

• Reacting solely to user feedback - Common user requests are usually table stakes and rarely lead to the novel innovations required for sustainable differentiation.
• Prioritizing speed bumps for users - Building features for management reporting often introduces friction into the primary user's day-to-day workflow, leading to feature bloat.
• Maintaining fragmented roadmaps - Keeping separate documents for design, product, and engineering fragments accountability and prevents true cross-functional alignment.
• Falling into the planning fallacy - Asking engineers for time estimates often leads to over-scoping; it is better to define a fixed appetite and reduce scope to fit.

Deep Dive

For all 50 sourced insights from 24 guests, see references/guest-insights.md

Related Skills

• Goal Setting Okrs
• Planning Cadence
• High Stakes Decisions
• Evaluating Trade Offs