All of our Decision-making articles

Starting Up

An Exact Breakdown of How One CEO Spent His First Two Years of Company-Building

Sam Corcos, co-founder & CEO of Levels, tracked exactly how he spent the two years since founding the company for a rare inside look at being a startup leader.

Starting Up

Counterintuitive Lessons on How to Get Better as You Scale, From Twilio’s Jeff Lawson

13 years after Twilio first launched, CEO and co-founder Jeff Lawson opens up about the peaks and valleys to share a set of unconventional company building lessons on how to get better as you scale — from introducing new products and refining go-to-market strategies to focusing annual planning.

Management

Focus on Your First 10 Systems, Not Just Your First 10 Hires — This Chief of Staff Shares His Playbook

As Chief of Staff at HashiCorp, Kevin Fishner focuses on treating the company like a product. Here, he unpacks why the systems side of company building doesn’t get as much attention and digs into the nitty-gritty details of how they set and track progress toward goals.

Product

Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products)

Product builders should aim for lovable, not just viable. Jiaona Zhang (product leader at Dropbox, Airbnb, WeWork and lecturer at Stanford) shares her tactics for building MLPs that win users' hearts.

Management

The Secret to a Great Planning Process — Lessons from Airbnb and Eventbrite

Poor planning can spell disaster for companies and sow distrust among teams. Drawing from their careers at Eventbrite and Airbnb, Lenny Rachitsky and Nels Gilbreth break down their "W Framework" to help startup leaders develop plans, earn alignment and execute effective planning cycles every time.

Management

The 6 Decision-Making Frameworks That Help Startup Leaders Tackle Tough Calls

Startup leaders make tough calls every day. We spoke with 6 top operators to gather the tactics and strategies they use to make smart decisions under pressure, garner trust with stakeholders and execute with conviction.

Management

I Asked 100 Founders, CEOs and VCs About Career Transitions — Here’s What I Learned

After founding and scaling LendUp for seven years, Sasha Orloff decided to step down as CEO. He shares his journey and his illuminating takeaways about career transitions, structuring time off and founder life after the startup.

Management

How This Head of Engineering Boosted Transparency at Instagram

While leading engineering at Instagram, James Everingham spotted a problem: the inevitable dip in transparent decision-making and communication as teams scale. Drawing on three decades of experience, he shares how to operationalize transparency during hypergrowth.

People & Culture

Betterment Tested Three Performance Management Systems So You Don't Have To

As Founder and CEO of Betterment, Jon Stein realized startups can't just establish one way to measure employee performance — they have to continually iterate as they grow. Here's how to do it well.

Management

What I Learned about Management and Culture from Growing Uber’s Asia Business from Zero to Billions

For four years, Mike Brown oversaw all aspects of Uber's business in Asia. Now he's sharing what startups can learn from his experience to go big.

Product

Make Product Decisions Without Doubt — My Lessons from Twitter and Slack

At Twitter and Slack, Tess Rosania built interfaces that millions use each day. Here, she dissects how she eliminated doubt from four high-stakes product decisions.

Product

The Habit Behind This Founder’s Fast Financings, Product Development and Book Deal

MissionU CEO Adam Braun has a habit that's helped him get term sheets in weeks, launch products and pen a bestseller. Here's an inside look at the practice that guides him.