technical-roadmaps

Name: technical-roadmaps
Author: refoundai

Help teams create written technical roadmaps aligned to business outcomes using structured frameworks. Applies the Rumelt framework to organize strategy into three parts: Diagnosis (core technical challenge), Guiding Policies (decision-making principles), and Actions (specific initiatives) Emphasizes documenting strategy in writing so it can be critiqued, improved, and aligned across teams rather than existing only in leadership's head Flags common pitfalls including tool proliferation, unwritten strategies, and technical work disconnected from business value Guides users to define a "standard kit" of approved technologies to reduce maintenance burden and focus engineering effort on product problems rather than technical novelty

INSTALLATION

npx skills add https://github.com/refoundai/lenny-skills --skill technical-roadmaps

Run in your project or agent environment. Adjust flags if your CLI version differs.

SKILL.md

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Boring strategies often win

Will Larson: "A common strategy that's really good but very boring is we only use the tools we have today. Engineers want to introduce new programming languages, new databases, new cloud providers. A really good strategy for almost all companies is we just use the standard kit we already have." Focus engineering energy on business-valued problems rather than technical novelty.

Use the Rumelt framework

Structure technical strategy using Richard Rumelt's framework: Diagnosis (what's the core challenge?), Guiding Policies (what principles will guide decisions?), and Actions (what specific things will you do?).

Create a standard kit

Define a list of approved tools, languages, and platforms. This limits technical sprawl and allows teams to focus on solving core product problems rather than reinventing infrastructure.

Questions to Help Users

"Is this technical strategy written down somewhere that anyone can reference?"

"What is the core technical challenge you're trying to solve (the diagnosis)?"

"What principles will guide your technical decisions (the guiding policies)?"

"Are you adding new tools because you need them, or because they're interesting?"

"What does your 'standard kit' of approved technologies look like?"

"How does this technical roadmap connect to business outcomes?"

Common Mistakes to Flag

Unwritten strategy - A strategy that only exists in someone's head can't be debugged or aligned around

Tool proliferation - Introducing new technologies when existing ones would work creates maintenance burden

No connection to business value - Technical roadmaps that don't tie to product or business outcomes lack justification

All diagnosis, no action - Good strategy requires specific actions, not just analysis of the problem

Missing guiding policies - Without principles, every technical decision becomes a debate from scratch

Deep Dive

For all 2 insights from 1 guest, see references/guest-insights.md

Related Skills

Managing Tech Debt

Platform Strategy

Engineering Culture

Prioritizing Roadmap