Reading List for Leaders in Uncertain Times

Editor’s note: Here are some of our best pieces on leadership, grit, and managing a startup in times of uncertainty, culled from our past (almost) decade of archives. 

On leadership

Peacetime CEO/Wartime CEO by Ben Horowitz: From Ben’s classic post: “Peacetime and Wartime management techniques can both be highly effective when employed in the right situations, but they are very different. The Peacetime CEO does not resemble the Wartime CEO.”

Which Way Do You Run? by Ben Horowitz: Most founders and CEOs have a gnarly gut instinct when something is wrong. What you do with that feeling? 

First Rule of Leadership by Ben Horowitz: We’re often told to “just be yourself” — and yet it’s so easy to try and be someone else, especially when you’re a founder or CEO. So why does it matter that you be yourself? And what are the unintended consequences if you don’t? 

Lead Bullets by Ben Horowitz: When facing a big, hairy problem, it’s natural to look for a silver bullet. The problem? Silver bullets rarely exist. 

🎙Improv’ing Leadership with Dick Costolo and Peter Levine: Leadership is about more than management — there’s also passion, humor, and resilience. Dick Costolo, entrepreneur and former CEO of Twitter, talks with a16z General Partner Peter Levine about the role of improv and imagery in leadership moments big and small.  

🎙& 🎥 Leading During Crisis with Susan Rice and Katie Haun: From becoming the youngest assistant secretary of state to her role as US Ambassador to the United Nations, Ambassador Susan Rice has learned what it means to drive forward in the face of challenges. In this discussion with a16z General Partner Kathryn Haun, Susan reflects on the many lessons she’s learned throughout her career, including how to be a tough yet compassionate leader in times of crisis.

On managing your own psychology and professional development

What’s the Most Difficult CEO Skill? Managing Your Own Psychology by Ben Horowitz: Of all the skills he’s had to master as a founder, CEO, and leader, the most difficult one for Ben has been how to master himself–and the same goes for hundreds of other CEOs he’s talked to. (Hint: if you’re the CEO, it’s always your fault)

The Struggle by Ben Horowitz: It’s all going great–until it’s not. That’s when you might find yourself in The Struggle. How do you survive? How do you not get not crushed?

🎙From Technical to Product to Sales CEO with David Ulevitch and Sonal Chokshi: When a16z General Partner David Ulevitch founded OpenDNS, little did he know the rollercoaster he had just boarded. From CEO to CTO back to CEO, from consumer to enterprise, from being acquired (by Cisco in 2015) to being the acquirer, David shares his journey and advice for founders–not least of which relates to how you manage your own psychology, and learn how to trust your leadership, in times of change.  

Bringing in an External CEO by Martin Casado: “To CEO or not to CEO?” a16z General Partner Martin Casado shares his journey founding Nicira Networks, title fetishism, and the tensions and nuances around “founder-led companies.” 

🎙Making Culture, Making Influence with Dapper Dan and Ben Horowitz: Dapper Dan is known for having pioneered high-end streetwear in the 1980s, but his story as a founder, gambler, and lifelong learner–hustler–who keeps reinventing himself through hard times has lessons for other makers and leaders.

On strategy

🎙Competing Against Luck with Clay Christensen, Marc Andreessen, and Steven Levy: Many smart businesses know that they could get disrupted, and yet it happens anyways–why? Clay Christensen, the author of The Innovator’s Dilemma, Harvard Business School Professor and the pioneer behind disruption theory, and a16z co-founder Marc Andreessen discuss the theories and frameworks that can help companies survive, in this conversation led by longtime tech writer and editor Steven Levy.   

🎙Startups, Pivots, Culture, and Timing (Oh, Shit!) with Ben Horowitz, Jason Rosenthal, and Sonal Chokshi: The hardest thing about the proverbial “pivot” isn’t just the actual pivot. It’s the courage to make the decision … and being honest with yourself as a CEO. In this conversation with a16z’s editor in chief Sonal Chokshi, Ben and Jason Rosenthal, the former CEO of Lytro (acquired by Google) discuss pivots and their wide-ranging impact on every aspect of a startup.

The “Oh Shit” Moment When Growth Stops by Jeff Jordan: One day, the business is growing. The next day, it’s not. What do you do now? a16z General Partner Jeff Jordan argues that, once growth slows or stops, it won’t just come back magically, and he shares a process for creating the right plan to fix it.

Who You Gonna Call? Navigating the Existential Crisis by John O’ Farell: When faced with an existential crisis, when sales and engineering may not be enough, what do you do? What are your options? a16z General Partner talks about the role of strategic business development and how it can lead to transformational opportunities for your company. 

🎙Innovating in Bets with Annie Duke, Marc Andreessen, and Sonal Chokshi: Every organization (and indeed, every individual) makes decisions every day under conditions of uncertainty. Annie Duke, the author of Thinking in Bets and a world-class professional poker player, talks with Marc and Sonal about thinking systematically about that uncertainty and how to use it to make better decisions.

On operations and managing the business

Cash Flow and Destiny by Ben Horowitz: While many founders have heard that “cash is king” from investors, the reason they should believe it is not because investors tell them so. It’s because cash is freedom. 

The Map and the Terrain by Ben Horowitz: Ben argues that, while the CEO and CFO have necessarily different perspectives on the business, each needs to work hard to understand the other’s and use that to build trust for when it’s time for difficult decisions.

🎙Navigating the Numbers with Jeff Jordan, David George, Caroline Moon, and Das Rush: What do the numbers — both in financial statements and KPIs — tell you? And what do they not? This episode covers the most common mistakes people make when it comes to understanding their numbers; how investors look at a company’s P&L; what metrics investors use to determine if a business is healthy; and how founders can use the numbers to navigate in times of crisis.

🎙Cash, Growth, and CEO <3 CFO with Ben Horowitz, Scott Kupor, and Caroline Moon: Balancing cash reserves vs. growth, advance planning vs. constantly changing strategy, revenue vs. margin, coordination/communication/culture, and so on is a lot harder than it seems on a finance spreadsheet. And this is why a tight, productive partnership between CEO and CFO is so important. 

SaaS Businesses Weather Hard Times by Focusing on Efficient Growth by Kristina Shen and Kimberly Tan: Though this article is focused on how SaaS businesses can survive amidst a volatile economic outlook, many of the principles discussed — focus on retention, acquire customers efficiently, manage runway actively — are useful for all kinds of startups and companies.

How to Make Meetings Efficient by Steven Sinofsky: Meetings: we all like to complain about them and rightfully so. Many meetings are bad. And yet, a16z Board Partner Steven Sinofsky writes, “In the course of building a company the most important tool you have to create a culture of shared values is communication and meetings are critical to communication.”

A Leader’s Guide to Deciding: What, When, and How to Decide by Steven Sinofsky: Steven writes: “I wrote this post in an effort to create a framework for how to think about decisions from the vantage point of a CEO/founder/exec as an organization grows beyond when the “hub and spoke” is the expected norm, and how to think about the good and crisis times when it comes to decision-making.” 

🎙Crisis Communications with Margit Wennmachers, Kim Milosevich, and Sonal Chokshi: How do you handle a crisis? In this episode with a16z Operating Partner for Marketing, Margit Wennmachers, and marketing partner Kim Milosevich talk with Sonal about the process, mindsets, and tactics for handling a crisis and ultimately, become a better company for it.

🎙Managing Uncertainty — Layoffs and Talent with Alex Rampell, Shannon Schiltz, and Sonal Chokshi: In many ways, managing startups is about managing uncertainty. So what happens when changes in the business require changes — and sometimes reductions — in the workforce? a16z Operating Partner Shannon Schiltz and a16z General Partner Alex Rampell share both their professional and personal experiences with layoffs — from why they happen to what to do (and what not to do).

Planning and Managing Layoffs by David Ulevitch: How you handle a layoff, how you communicate it to the people impacted, and how you manage and lead throughout the process really matters. It requires careful thought and planning, as David shares in this comprehensive guide, and it might be the most important thing you do as a leader.

 

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