Drawer 12 · 724 notes · 95 people · 2005–2026

Execution, roadmaps & process

Roadmaps, prioritization, planning, shipping, and working with engineering

Q:
Answers from Execution, roadmaps & process notes, cited
SVPG · Marty CaganFeb 24, 2022

Failure as a Springboard to Success

Feb 24, 2022 · 3 min

This essay recounts how Datasite, a SaaS provider for dealmaking, rebuilt its outdated platform under pressure to keep clients from leaving. When the platform failed during a beta launch with an Irish client, the…

Lenny’s Podcast128 min

Inside ChatGPT: The fastest-growing product in history

Nick Turley · Aug 9, 2025
Key learnings
  • Ship early to learn what people actually want; with AI, the valuable behaviors are emergent, so you won't know what to polish…
  • Treat the model itself as a product: iterate on it using real user use cases, personality/vibe checks, and new capabilities like…
  • Set the team's pace deliberately by asking whether work is 'maximally accelerated', separating fast product iteration from…
SVPG · Marty CaganJul 1, 2018

Scaling Agile FAQ

Jul 1, 2018 · 6 min

Marty Cagan follows up on his critique of SAFe, the scaled-agile framework, by answering reader questions. He argues that process choices are really culture choices, and that adopting a heavy framework signals top-down…

Lenny’s Newsletter♥ 263

How Shopify builds product

Jul 25, 2023 · 20 min
Subscriber post — summary only

An interview with Shopify's VP of Product, Glen Coates, on how the company plans around annual CEO themes, avoids OKR-style metrics ownership, reviews work through a staged system, and structures teams around merchant…

SVPG · Marty CaganFeb 18, 2010

Dedicated Product Teams

Feb 18, 2010 · 5 min

Marty Cagan contrasts two ways of organizing product work: project-based feature teams that get reshuffled around a communal roadmap, and dedicated product teams that persist around a business area. He argues that…

Product Talk · Teresa TorresJan 6, 2014

The Three Pillars of Building Great Products

Jan 6, 2014 · 5 min

“Do you know what it takes to build great products? Are you so confident in your approach that you know that your product will be a success? I’m not. I’m often filled with doubt. Even when things are going well, I wake up at night worried that it’”

Lenny’s Podcast99 min

The engineering mindset

Will Larson · Jan 7, 2024
Key learnings
  • Treat engineers as capable adults by giving them hard problems and accountability, which lets them grow into senior leadership…
  • Build simple stock-and-flow models of processes like hiring pipelines, then compare them against historical data to find where…
  • Write your engineering strategy down, even imperfectly; an unwritten strategy cannot be debugged or improved, and every function…
Lenny’s Podcast100 min

The non-technical PM’s guide to building with Cursor

Zevi Arnovitz · Jan 18, 2026
Key learnings
  • Start slowly with a ChatGPT project acting as a skeptical 'CTO' before moving to coding tools, gradually easing into code to…
  • Capture ideas quickly as Linear issues using reusable slash commands, so you can pick them up later with context already gathered.
  • Separate the workflow into explore, plan, execute, review, and document phases, and have the AI ask clarifying questions before…
SVPG · Marty CaganSep 20, 2015

Roadmap Alternative FAQ

Sep 20, 2015 · 6 min

Marty Cagan answers the most common questions readers raised after his article proposing an alternative to conventional product roadmaps. He argues that engineers should help decide what to build, that outcome-based…

Lenny’s Newsletter♥ 86

How Snowflake builds product

Jul 11, 2023 · 17 min
Subscriber post — summary only

An interview with Snowflake's Director of Product for its Developer Platform and Ecosystem, describing how the company plans, reviews, and organizes product work. It covers annual 'big boulder' planning, six-page plan…

Lenny’s Podcast84 min

Building Substack

Sachin Monga · Oct 30, 2022
Key learnings
  • Early on, act more as a facilitator than a decision maker: keep the CEO and teams aligned on problems and vision through a…
  • Organize product teams around timeless customer problems (writers, readers, growth) rather than product surfaces, so structure…
  • Expect any process or planning system to become obsolete as the company grows; aim to keep getting better each week, month, and…
SVPG · Marty CaganOct 12, 2009

The Product Discovery Plan

Oct 12, 2009 · 4 min

Cagan argues that teams who genuinely value product discovery still waste time when they lack a plan, so they should write a Product Discovery Plan spelling out who is involved, what must be done, what resources are…

Lenny’s Podcast148 min

Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history

Amol Avasare · Apr 5, 2026
Key learnings
  • Expect most growth time to go to 'success disasters' once growth is rapid; firefighting breaking systems matters as much as new…
  • In AI-first products, skew the growth portfolio toward larger swings, since future product value could be orders of magnitude…
  • Treat activation as a top lever in AI products: identify user traits that predict which feature fits them, then guide them there.
SVPG · Marty CaganJul 9, 2021

Discovery vs. Design

Jul 9, 2021 · 3 min

Marty Cagan asks whether product discovery applies to feature teams, which are handed a list of features rather than problems to solve. At a simple level, discovery is irrelevant there because the solution is already…

Product Talk · Teresa TorresMar 18, 2015

Fix Delivery to Make Time for Discovery

Mar 18, 2015 · 3 min

Teresa Torres argues that many product managers are so consumed by delivery work (grooming backlogs, triaging bugs, handling schedule slips) that they lack time for discovery, the work of figuring out what to build. Ad…

Lenny’s Podcast104 min

What sets great teams apart

Lane Shackleton · Oct 1, 2023
Key learnings
  • Treat the core job of product work as turning ambiguity into clarity, and build repeatable systems rather than chasing one-off…
  • Build default-on customer contact systems, such as a standing weekly slot with customers, instead of quarterly OKRs to talk to…
  • Ask career questions about how many 'oh shit' moments someone has had recently, a sharper signal of growth than asking whether…
@lissijean · Melissa Perri on X♥ 9
Scaling product teams is hard. Delivering consistent outcomes while keeping things simple is even harder. Mark Rosenberg, VP of Product at @Workday shares how revamping ProdOps reduced complexity, aligned teams, and delivered better outcomes at scale. 🎧
Lenny’s Newsletter · Free post♥ 239

The Best of Lenny’s Newsletter 2021

Aug 17, 2021 · 6 min

This is a curated index of Lenny Rachitsky's best newsletter posts from his first two and a half years, organized into nine topics such as growth strategy, product management work and career, product-market fit…

Lenny’s Newsletter♥ 13

Defending your big bets

Mar 16, 2021 · 6 min
Subscriber post — summary only

Lenny answers a reader's question about keeping support for a long-term 'big bet' project at a large company. His core argument is that steady, visible wins (the 80/20 split of incremental work and high-risk work) earn…