Technical Roadmaps
Technical roadmaps align engineering work with business strategy by documenting what you're building, why, and how. Without a written strategy, teams can't debug misalignment or improve their approach. The best technical roadmaps constrain choices to focus engineering energy on high-value problems.
The Guide
3 key steps synthesized from 1 experts.
Write it down, even if it's imperfect
A documented strategy is the foundation for alignment and improvement. If your technical direction lives only in people's heads, you can't tell whether execution problems stem from bad strategy or misunderstanding. Even a mediocre written strategy gives you something to debug and iterate on.
Featured guest perspectives
"The first rule of strategy is that if you write it down, then you can improve it. If it's not written down, it's hard to say if this PM is just not a good PM or if they're trying to apply the strategy that they've misunderstood... If you have a written document, even if it's not a super compelling strategy, at least you can start debugging."— Will Larson
Use the Diagnosis-Policy-Action framework
Structure your roadmap around three elements: a diagnosis of the current situation and challenges, guiding policies that define your strategic constraints, and specific actions that implement those policies. This framework (from Richard Rumelt) prevents roadmaps from becoming vague wish lists.
Featured guest perspectives
"Use the Richard Rumelt framework: Diagnosis, Guiding Policies, and Actions"— Will Larson
Embrace boring, constraining strategies
Some of the most effective technical strategies are 'boring' constraints that prevent sprawl. A policy like 'we only use the tools we already have' channels engineering energy toward solving business problems rather than chasing technical novelty. Create a 'standard kit' of approved tools and resist the urge to introduce new languages, databases, or frameworks without compelling justification.
Featured guest perspectives
"A common strategy that's really good but very boring is we only use the tools we have today. So a lot of times you'll get engineers that want to introduce new programming languages, new databases, new cloud providers. And a really good strategy for almost all companies is like we just use the standard kit we already have today."— Will Larson
Common Mistakes
- Keeping the strategy in people's heads where it can't be debugged or aligned on
- Allowing tooling sprawl by approving new technologies without strong business justification
- Focusing on technical novelty rather than solving core business problems
Signs You're Doing It Well
- Team members can articulate the technical strategy and explain why specific decisions align with it
- Engineers spend most of their time solving business problems, not debating tooling choices
- When execution problems arise, you can trace them to strategy issues versus misunderstanding
All Guest Perspectives
Deep dive into what all 1 guests shared about technical roadmaps.
Will Larson
"The first rule of strategy is that if you write it down, then you can improve it. If it's not written down, it's hard to say if this PM is just not a good PM or if they're trying to apply the strategy that they've misunderstood... If you have a written document, even if it's not a super compelling strategy, at least you can start debugging."
- Document the strategy even if it is imperfect to allow for 'debugging' and alignment
- Use the Richard Rumelt framework: Diagnosis, Guiding Policies, and Actions
"A common strategy that's really good but very boring is we only use the tools we have today. So a lot of times you'll get engineers that want to introduce new programming languages, new databases, new cloud providers. And a really good strategy for almost all companies is like we just use the standard kit we already have today."
- Create a 'standard kit' of approved tools to limit technical sprawl
- Focus engineering energy on business-valued problems rather than technical novelty
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