All of our Planning articles

Starting Up

Building a Deep Tech Company? Most Startup Advice Doesn’t Apply — Read This Instead

Learn from Loyal founder Celine Halioua’s rigorous approach to milestone-based planning, fundraising and multi-product strategy for deep tech companies.

Management

Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better

Four top execs reveal their annual planning secrets from Notion, Stripe, Vanta, Linear, Linktree and more. From addressing AI to adjusting org charts, this COO, CFO, CPO & CRO share insights so startups at any stage can build effective, realistic plans.

Management

The Silent Killer of Your Operating Practice: Fear

Amanda Schwartz Ramirez, former PayPal strategy leader and now COO advisor for startups, shares the 5 biggest fears that can derail your company's strategic planning sessions (and tactical advice for how to sidestep them).

Management

How to be an Exceptional Chief of Staff: Advice for Scaling Impact at Startups

10 tactical tips and guiding principles for a new Chief of Staff to lean on as they scale their impact at a startup — from building better systems, not just booking more meetings and finding an executive's superpower.

Must-reads

Annual Planning in Uncertain Times: 6 Tactics for Rethinking Your Company’s End-of-Year Exercise

We’ve combed the extensive Review archives for a timely roundup of the most unique advice for end-of-year strategic planning. Leaders like Lenny Rachitsky, Nels Gilbreth, Jeff Lawson, Annie Duke, Ravi Mehta and more share the inventive frameworks they lean on for this annual exercise.

Product

How Product Strategy Fails in the Real World — What to Avoid When Building Highly-Technical Products

Why does strategy tend to stall when the rubber hits the road? Nate Stewart, Chief Product Officer of Cockroach Labs, shares an essential guide for creating a resilient strategy that’s still standing next year.

Engineering

“Get Off the Floor” and Other Career Advice from Microsoft, Looker, Reddit & Twitter

Nick Caldwell's resume includes an enviable list of companies — Microsoft, Reddit, Looker and Twitter. He shares his biggest lessons from each for a crash course in finding success across different company cultures, scales & functions.

Management

The Founder's Field Guide for Navigating a Crisis — Advice from Recession-Era Leaders, Investors and CEOs Currently at the Helm

We've tapped First Round partners, recession-era founders and our community of CEOs to put together the most comprehensive guide available about what it takes to lead a startup during this economic crisis. From extending your runway and reducing burn to supporting your team, this guide tackles the t

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.

PR & Marketing

How New Startups Can Win at PR — Advice from a 20-Year Comms Career

Terra Carmichael leverages two decades of comms experience with companies like Eventbrite, Yahoo, Mattel, Nike and more to dispense advice to young startups finding their footing with the press.

Product

My Launch Lessons from 37 Minutes in an Amazon War Room

Before joining Twitter, Ibrahim Bashir led the launch of the third-generation Kindle at Amazon. Here, he reflects on his lessons from that release — and shares how to prepare to make hard decisions quickly when the unexpected happens.

Management

What Obama’s Tech Startup Has to Teach About Adaptability

USDS marketing chief and former head of marketing for Google X Janine Gianfredi shares her lessons on how to build adaptable teams, even in the most rigid and regulated environments.