Iteration & feedback loops
Podcast
How to build AI evals: a practical guide for product builders
Lenny's Podcast Product Career Growth
September 25, 2025
Iteration & feedback loops
9
AI tools & automation
8
Roadmapping
6
- Skip straight to tests and your eval process will fail.
- A binary LLM judge beats any 1–5 scoring scale every time.
- Three days of setup, then thirty minutes a week improves everything.
How product teams can align their work to business-critical outcomes
Lenny's Podcast Product Career Growth
August 14, 2025
Roadmapping
9
Business operating systems
6
Management
5
- Why doing OKRs 'the right way' won't save your job
- Set team goals one step from company goals — no more
- Low-impact work compounds until the next round of layoffs
Shape Up: A better way to plan, build, and ship products
Lenny's Podcast Product Career Growth
March 30, 2025
Roadmapping
9
Processes & SOPs
7
Iteration & feedback loops
6
- Six-week cycles eliminate planning meetings and reduce scope creep.
- Pitches let teams present finished designs upfront for commitment.
- Batch work into no-interruption periods to avoid context switching.
An operator's guide to product strategy
Lenny's Podcast Product Career Growth
January 26, 2025
Roadmapping
8
Long-term planning
7
Management
6
- Balancing strategy and execution through operating model design
- Building cross-functional influence and organizational credibility
- Creating decision frameworks that scale product decision-making
Building a product team from scratch: lessons from Mercury and Square
Lenny's Podcast Product Career Growth
January 12, 2025
Roadmapping
9
Hiring & recruitment
8
Customer discovery
6
- Mercury ran 400 employees with zero PMs — until bottlenecks forced the shift.
- Pioneer, settler, city planner: match PM type to product stage, not just resume.
- Structural separation is the secret to launching multiple new products without killing them.
Staying a senior IC PM for 12 years: lessons from Tal Raviv
Lenny's Podcast Product Career Growth
September 22, 2024
Roadmapping
8
Deep work & focus
7
AI tools & automation
6
- Why staying an IC PM for 12 years beats moving into management
- Dictating to ChatGPT replaces an entire Scrum Master function
- Every company has two departments that drive 10x outcomes — find them first
Building product at ops-heavy companies: lessons from Uber and Opendoor
Lenny's Podcast Product Career Growth
August 4, 2024
Roadmapping
9
Processes & SOPs
8
Management
6
- Why deep ops experience makes fundamentally better product leaders
- How to run experiments when transaction volume is too low for AB tests
- Technology should only go where leverage exists — say no everywhere else
The full-stack PM: frameworks for product strategy and leadership
Lenny's Podcast Product Career Growth
December 7, 2023
Roadmapping
9
Business models
8
Management
7
- New users are lazy, vain, and selfish — design onboarding accordingly
- Write three divergent PR FAQs before committing to any direction
- The 4BB framework turns resource allocation into a strategy conversation
How to build and communicate a compelling product vision
Lenny's Podcast Product Career Growth
December 3, 2023
Roadmapping
9
Customer discovery
7
Culture building
6
- Most PMs skip vision entirely — here's the full framework.
- Clarity on the problem beats any roadmap or strategy deck.
- Evangelise in three circles: team, stakeholders, then leadership.
What makes great product managers: habits, strategy, and craft
Lenny's Podcast Product Career Growth
November 5, 2023
Roadmapping
8
Productivity & habits
7
Vision & mission
5
- Why 'data-driven' culture is often a red flag for product thinking
- A structured doc template for writing strategy from mission to plan
- The three unglamorous habits that separate great PMs from good ones
Iteration & feedback loops
Podcast
Moving from opinion-based to evidence-guided product development
Lenny's Podcast Product Career Growth
September 21, 2023
Iteration & feedback loops
10
Customer discovery
7
Roadmapping
6
- Google+ wasted ~1,000 people; the tabbed inbox hit 1.8 billion users
- A confidence meter shows when your impact estimates are just opinions
- Outcome roadmaps beat feature roadmaps — ship learning milestones, not releases
Four steps to building an online course curriculum that sells
Sunny Lenarduzzi
September 5, 2023
Roadmapping
9
Content marketing
6
- Clients buy transformation, not information — stop overstuffing.
- Build the curriculum backwards from the hero outcome, then subtract.
- Test live before recording; micro-wins generate early social proof.
Product-market fit
YouTube
Five principles for building software products customers pay for
Dan Martell
June 19, 2023
Product-market fit
9
Roadmapping
8
- Without a written product vision, teams pull in opposite directions.
- Cross-functional pods let companies ship hundreds of times per day.
- Ignore the HIPPO — customer data beats the highest-paid opinion.
How Miro builds product: Lessons on competition and moving fast
Lenny's Podcast Product Career Growth
April 20, 2023
Roadmapping
9
Iteration & feedback loops
7
Competitive analysis
6
- Every product release gains or loses ground; competing on chess moves clarifies what to prioritize.
- Cross-functional teams with embedded product marketing resist siloing and commodity traps.
- Speed to learn beats perfection; unblock teams to hit the brick wall first.
Building product strategy and scaling sales at Calendly
Lenny's Podcast Product Career Growth
February 26, 2023
Roadmapping
9
Business models
7
B2B sales
6
- Shift from horizontal PLG to targeted personas drives faster product prioritization and execution
- Calendly's three-horizon strategy allocates resources by market maturity, not feature volume
- Founder raided 401k, hired Ukrainian firm, and got first 1,000 users through contractor networks