Getting Comfortable Between ‘Yes’ and ‘No’: An Important Lesson for Startup CEOs

There are CEOs who say "yes" to nearly everything, those who prioritize and say "no" -- and, of course, leaders who fall somewhere in between. In a post earlier today on Fast Company, I discuss the pros and cons of each style and lessons I've learned as a startup CEO myself. The byline is excerpted below, but be sure to check out the entire article over at Fast Company:

Maybe it’s not a question startup CEOs ask themselves, at least not explicitly: Am I a "Yes Man" or a "No Man"? Am I more inclined to encourage growth in all directions, or would I rather my team prioritize only the most important initiatives? Well, the answer hints at your personality, your previous job experiences, and the bosses you’ve worked with.

My leadership style has been influenced by a number of executives I’ve admired over the years—Dave Duffield, Ben Horowitz, Parker Harris—but none more than Marc Benioff, whom I worked for while heading up engineering at for more than six years. Marc’s known for saying "yes" to almost everything. He’d rather encourage a lot of disparate ideas and see what works, instead of risking saying "no" to one that could ultimately turn into something great. (Case in point: They announced a number of new products at last week’s Dreamforce, one of which is competitive to my company’s product.)

Everybody likes to hear "yes"—well, most people—but now, as a startup founder and CEO, I’ve found it’s equally as important to learn how to say "no" in order to keep teams focused, functional, and productive. Saying "yes" isn’t always a luxury that startup CEOs can afford, and finding that middle ground can be among the most difficult, but important, lessons to learn.

A Revolving Door of Ideas

Marc is a big proponent of the "try-it-and-see-what-happens" approach. He pushes teams in all directions and lets them roam in others he hadn’t even considered. Consider’s recent acquisitions as an example of this style. During the past 18 months, the company has acquired more than 10 different companies, including task management company ManyMoon (now, customer service vendor Assistly (now, performance management company Rypple, social media marketing companies Buddy Media and Radian6, and a number of others. Almost all of them are flourishing today (or have been rolled into entirely new offerings), at least partly because Marc was open to opportunities outside of’s core CRM focus.

But saying "yes" too often has its drawbacks, too, especially for startups that lack the resources of a company as big and influential as A healthy dose of curiosity is essential, but startup CEOs can’t lose sight of their core product.