All of our Decision-making articles

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

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.
How This Head of Engineering Boosted Transparency at Instagram

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

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

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

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

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.
This Matrix Helps Growing Teams Make Great Decisions

This Matrix Helps Growing Teams Make Great Decisions

As CTO of Flatiron Health, Gil Shklarski has had to keep a rapidly-growing technical team aligned through many tough decisions. This is the framework that works every time.
Our 6 Must Reads for Scaling Yourself as a Leader

Our 6 Must Reads for Scaling Yourself as a Leader

To succeed in tech, you have to grow not just your skills, but also your energy, your time management, and your approach to work. This is a good place to start.
To Grow Faster, Hit Pause — and Ask These Questions from Stripe’s COO

To Grow Faster, Hit Pause — and Ask These Questions from Stripe’s COO

Claire Hughes Johnson is the woman overseeing Stripe's rocketship ascent. Here, she shares a list of questions that any startup can use to guide hyper-growth.