Insights

The Certainty Paradox
We all crave clarity in our work. It means knowing what we should focus on, in what priority, and what we can safely ignore. But in providing that clarity, a leader makes explicit tradeoffs among the various things the team might focus on. And when it’s a tough decision, the conviction to support clear direction is often hard to find.
Founder & CEO
Inkling
When to Be Strategic and When to Just Execute
A big challenge of leadership is trading off strategic and tactical thinking. When do you keep your head down and execute (getting things done) and when do you pop up and look around (am I getting the right things done)? Here's how I think about it.
Founder & CTO
Hearsay Social
How I Make Decisions
Being a founder is different than any other job. For me, the revelation was suddenly being the guy who made the decisions. I’d made decisions before, but there was always someone who could overrule me or take accountability.
Todd McKinnon
Co-Founder & CEO
Okta

Recommended Reading

Leadership and Self-Deception: Getting Out of the Box
(amazon.com)
This is a quick but thought-provoking read which challenged my views about myself and my employees. The authors do a good job of explaining how as leaders and as human beings, we all share a natural tendency to self-deceive, often at the expense of others, in order to justify our own actions. In a high-pressure startup environment, it is too easy to fall into this trap and let conflicts fester. This book walks through how to honestly self-evaluate, reframe/resolve conflicts, and grow as a leader/colleague/partner in your personal and professional life.
Founder & CEO
Hearsay Social
12 Things Good Bosses Believe
(blogs.hbr.org)
I keep a copy of this list taped to my desk and my mirror at home. Clara has it on her desk too. It encompasses how I like to lead and it’s a no bullshit reminder of what it’s like to be a founder. A founder gets vaunted status but I’m just the guy who happened to write the first lines of code. One of them is: “I have a flawed an incomplete understanding of what it feels like to work for me.” People perceive you differently so you need to change how you act.
Corner Office
(projects.nytimes.com)
This bi-weekly feature in the New York Times highlights CEOs talking about leadership and management. It helps me understand how other CEOs think and attack the world, and the cadence and aggressiveness that I need to employ to be successful.
Ryan Smith
Founder & CEO
Qualtrics
Being the Boss: The 3 Imperatives for Becoming a Great Leader
(amazon.com)
Touches on why being a boss is hard and paradoxes of human nature abound.
Bill Coughran
Sequoia
Getting Things Done: The Art of Stress-Free Productivity
(amazon.com)
A series of small hacks to optimize your life for accomplishing things. A phenomenal book and massively life changing. I’ve read it four times.
Founder & CTO
Hearsay Social
What's The Most Difficult CEO Skill? Managing Your Own Psychology
(bhorowitz.com)
This post encapsulates the many demons that overachieving individuals often encounter when they take on the CEO role. It's an incredibly useful read because it forces you to realize that (1) you're not alone (2) dealing with the turmoil is just a part of the job and (3) other people are struggling with it, too. Re-reading this post when things are going sideways at your company can help reset your own psychology, put you in a healthier, sounder place and allow you to reserve your emotional energy for the job at hand.
CEO
TokBox

Pricing Podcast

Featuring Evernote's Phil Libin and Sequoia's Roelof Botha

Listen on TuneIn or iTunes