Is Being A “Yes” Leader Asking For Trouble?

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.

Is Being A “Yes” Leader Asking For Trouble?

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.

Not Making Decisions Is a Decision

Contrast Benioff’s style with equally iconic leaders on the other end of the spectrum where it’s all about priorities. Steve Jobs famously filtered out what he called distractions, those projects that were outside of the company’s core focus. (He famously advised Google CEO Larry Page on product strategy, saying, “What are the five products you want to focus on? Get rid of the rest, because they’re dragging you down.”)

When you’re at the helm of a company–whether it’s a software startup or a worldwide corporation–saying “yes” to everything does encourage innovation but at the cost of forfeiting all ability to decide. Eventually, decisions have to be made, and when they are certain projects are prioritized, whether it’s the CEO or a lower-level manager pulling the trigger. Someone has to set the budget, hire the correct people, and greenlight the proper projects.


CEOs who say “no” and try to focus do get to decide what happens–but they’d also better be right more frequently than not. And to pull that off time and time again isn’t easy.

Stay Focused and Say “No”–At Least at First

In software development (I’m an engineer at heart) there’s a philosophy called agile development–it even has a manifesto–that calls for the iterative and incremental development of an idea. To achieve this, teams set aside a block of time, during which they build something without changing it. By focusing on one project for a month by essentially saying “yes” to something and “no” to a bunch of other things, they create something, even if it’s imperfect. And at the end of that period, the idea is to re-evaluate the project, see how it can be improved upon, and consider how it fits into the bigger context of the company’s goals. That’s often a good way for startup CEOs to work. Focus on one thing, and say “no” to everything else–but have the discipline to evaluate, re-evaluate, and make sure you’re heading in the right direction. Startups, after all, aren’t created in a bubble, and CEOs must not lose sight of what’s happening around them, even while they focus on a single initiative. The ability to multitask is right up there with the ability to make hard decisions in most CEO job descriptions.

Not Apple, Oracle, or–At Least Not Yet

CEOs looking to emulate the leadership styles of Steve Jobs, Larry Ellison, Marc Benioff, and other prominent technology executives should be aware of one (albeit huge) caveat: These men are famous because they’ve led hugely profitable, public companies. And looking at any one of them, one might think there are two ways to run a company. It’s not that simple. Startup CEOs likely don’t have the resources to say “yes” to every idea. But they’re also starting a company in a growing and dynamic market, so they can’t risk saying “no” to game-changing ideas.

My own personal style falls somewhere in the middle of “yes” and “no.” Often, not making a decision just feels lazy to me, like I’m not doing my job as CEO. And while I don’t shy away from being decisive, I also try to remember that it’s very difficult to be right all of the time. And that’s where I lean on my team to help me make the right decision, get me back on track when I don’t, and bring to light new ideas that I perhaps never even considered.

So, which approach is right for you and your company? It all depends, but know that there are trade-offs to both approaches. Have an open mind and a healthy dose of curiosity. Say “yes” and hold on. But also realize that you don’t have the resources to execute on everything and that you’ll have to say “no.” Be decisive–but be humble enough to know that you’ll be wrong occasionally, too.

What’s the better strategy–saying “yes” the majority of the time,” or saying “no”? Tell us about it in the comments.

[Image: Flickr user Jessica Feis]

About the author

Todd McKinnon is the CEO and co-founder of Okta, the first cloud-based identity management platform. Founded in 2009, Okta helps companies of all sizes secure their users, applications and data — both in the cloud and behind the firewall — so work gets done, from any device, anywhere