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118 insights from Lenny's newsletters and podcasts

This Week #2: Tackling the chicken-and-egg problem, building a growth team from scratch, and addressing overlap with PM peers 🤔

Sep 2019

Growth compounds from retention, not conversion

Early percentage improvements in conversion have poor ROI. Once retention is healthy, the biggest growth wins come from top-of-funnel activities like referrals, performance marketing, and SEO—not from squeezing another 2% out of your funnel.

Insightnewsletter

This Week #2: Tackling the chicken-and-egg problem, building a growth team from scratch, and addressing overlap with PM peers 🤔

Sep 2019

The worst thing you can do is nothing

Organizational friction around overlapping roles rarely resolves organically. These issues compound over time and require active management—either direct conversation with the peer, escalation to managers, or structural changes like title or team reassignment.

Quotenewsletter

This Week #2: Tackling the chicken-and-egg problem, building a growth team from scratch, and addressing overlap with PM peers 🤔

Sep 2019

Roles clarify through ideal-state thinking

When role overlap creates tension, don't negotiate based on current reality. Instead, work backward from what the ideal organizational structure should be as you scale—what skillsets should each role require? What's the career progression? This reframes the conversation from territorial to strategic.

Insightnewsletter

This Week #2: Tackling the chicken-and-egg problem, building a growth team from scratch, and addressing overlap with PM peers 🤔

Sep 2019

Bootstrap supply before demand

In marketplace cold-start problems, you're almost always supply-constrained first. Rather than trying to attract both sides simultaneously, focus on seeding supply through single-player mode, employee participation, or direct payment—this naturally draws in the demand side later.

Insightnewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

Execution clarity precedes strategic vision

Before developing strategy, ensure everyone knows what they should be doing, unnecessary meetings are eliminated, blockers are addressed quickly, and deadlines are clear. You can't build a compelling vision on top of a chaotic foundation.

Insightnewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

Quick wins build credibility faster than grand plans

Find 2-3 quick wins in your first 30 days that make the lives of the team better—unblocking a blocker, resolving a lingering decision, or improving an annoying process. Small, visible improvements establish you as someone who delivers before you attempt to reshape strategy.

Insightnewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

The roommate test for organizational trust

Even though you've interviewed someone and done extensive reference checks, you're still a little skeptical, not sure you want to trust them with the keys to the house. This metaphor captures why new team members must earn trust through actions before they can drive change.

Quotenewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

Experience beats credentials for PM advancement

When hiring for lead PM or director roles, nothing beats experience doing the actual job. An MBA is rarely worth it if you already have a PM position—there are better ways to accelerate your career through mentorship, working on diverse products, and switching to stronger teams.

Insightnewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

Trust before strategy: the 30-60-90 framework

A new PM joining a team is like a new roommate moving in—people are skeptical and wondering if they can trust you with the keys. Spend your first 30 days building trust through questions and quick wins, your next 30 improving execution, and only then develop your strategic point of view. Strategy without trust is dead on arrival.

Insightnewsletter

This Week #1: Must reads on growth, what PMs should focus on when joining a new team, and the value of an MBA

Sep 2019

Learning happens through doing, not reading

Don't let yourself get overwhelmed by frameworks and best practices. The folks you're reading have learned a few things by going through the same process you're about to go through. You'll learn most by doing—take a few ideas at a time, discuss them with your team, and try them out in the real world.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Strategy clarity is a team-wide test

If you ask anyone on your team what your strategy is, would they be able to explain it? If not, your strategy isn't clear enough. A strategy that only lives in the PM's head isn't a strategy—it's a secret.

Questionnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Make trade-offs visible, don't hide them

When asked to change plans, be transparent about what will suffer and what will benefit. Don't assume your manager knows what you know. Partner with them to make the best decision by surfacing the full picture.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Expectations shape how your work is judged

Your performance will be judged based on how it compared to your manager's expectations, not against an absolute standard. Set realistic expectations upfront, then exceed them—this is more powerful than doing great work against unknown benchmarks.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Differentiation is a choice, not a requirement

You can differentiate across 20+ dimensions—price, quality, experience, trust, tribe, story—or you can choose not to differentiate significantly and win by scaling faster. The best companies combine multiple dimensions, but some winners succeed purely through execution velocity.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Execution, strategy, vision—the PM's productivity stack

When your team is humming, work your way up from execution (blockers, processes, goals) to strategy (clarity, boldness) to vision (North Star, purpose). Each level builds on the last, and most PMs skip steps by jumping to vision without solid execution.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Over-communicate relentlessly with your manager

It's nearly impossible to over-communicate. Share what you plan to do, what you're doing, and what you did through consistent updates. A weekly 'State of Me' email covering blockers, priorities, and concerns creates alignment and prevents misalignment.

Insightnewsletter

This Week #0: Advice on growth, product, and leadership

Sep 2019

Performance determines autonomy, not vice versa

If you feel micro-managed while others around you don't, it's likely because you aren't performing well. Do great work and life will get better. Trust and freedom are earned through execution, not granted by position.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Crystallize your opinion before peer feedback arrives

Form your own assessment of performance before reading peer feedback. This critical step reduces bias and prevents you from being completely swayed by what others say, allowing you to triangulate rather than defer.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Start gathering feedback a month in advance

Begin the feedback collection process at least a month before a scheduled performance conversation, since it often takes time to get everyone's responses. Early starts reduce rushed decisions and allow patterns to emerge.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

One or two development areas, not a laundry list

More than two development areas makes it very hard to make meaningful progress on any of them. Specificity and constraint force clarity about what actually matters most for the next level.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Bias hides in how we describe the same behavior

Many managers unconsciously describe the same behavior by men as a strength and as a weakness by a woman. Awareness of this pattern is essential when identifying superpowers and development areas.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Preparation is where the real work happens

The bulk of your time should be spent in preparation—gathering peer feedback, soliciting self-assessment, and crystallizing your own opinion before the conversation. This stage sets up everything that follows and reduces bias.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Strengths compound more than weaknesses shrink

An individual will have just as much impact (if not more) on an organization if they flex what they are really good at, instead of just trying to improve on areas they're struggling with. Research shows focusing on strengths is much more effective than obsessing over weaknesses.

Insightnewsletter

The Power of Performance Reviews: Use This System to Become a Better Manager 🤝

Jul 2019

Performance reviews are the secret weapon

Done well, performance reviews improve performance, align expectations, and accelerate careers. Done poorly, they accelerate departure. This single tool may be the highest-leverage intervention a manager has.

Insightnewsletter

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