I had a choice: pull the plug on a  collaboration I'd been negotiating for weeks, or promote a product that didn't completely align with my business. Either way, I risked losing short-term growth, long-term reputation, and relationships in the industry.

Where's that crystal ball when you need one?

Leading an organization is not a walk in the park, especially when it comes to decision making. The bigger your business, the bigger the decisions you have to make, and the more quickly you have to make them. Worse, the bigger your business, the higher the stakes--not just for you personally, but also for your employees, investors, and customers.

And since you're the leader, if the decision you make is a poor one, you have nobody to blame but yourself.

Decision making: Nobody said it was easy.

Decisions are binary--you can go left or right. But certainty is not. You're rarely 100 percent sure of one alternative over another. Worse, sometimes options appear equally good, or equally bad.

And, of course, not deciding is the worst, because then circumstances will make the decision for you.

Ben Horowitz considers decision making one of the hard things about leading a business. In The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Horowitz says, "Hard things are hard because there are no easy answers or recipes. They are hard because your emotions are at odds with your logic. They are hard because you don't have the answer and you cannot ask for help without showing weakness."

Decision making can be particularly difficult for leaders who are "twos," according to Horowitz. "Ones" are comfortable with making critical decisions, even if they have insufficient data. They don't get overly anxious about the consequences. In contrast, twos get eaten up by making big decisions in the face of uncertainty. They prefer to execute rather than make big, strategic decisions.

But whether you're a one or a two, you can't escape making critical decisions.

The solution? There is no solution.

There are no magic formulas for correct decision making. This doesn't mean you should make careless decisions. If you're not sure which way to go, because you need more information, then by all means get as much information as you can in the time you have available. Management consulting firm McKinsey & Company found that strategic planning processes and quality discussion generate good decisions.

But if it's not likely that you're going to get much more sure, then make the best decision you can with the information you do have.

Horowitz also advocates for CEOs to systematically gather knowledge as they go about their daily activities, so that when decision making time comes, they will already have as much information as they need. These are some of the questions he says CEOs must always be asking:

  • What are the competitors likely to do?
  • What are the true capabilities of the organization and how can you maximize them?
  • How much financial risk does this imply?

Get comfortable with the discomfort.

Let go of the expectation that you'll always make the right decision. Even Warren Buffett admits, "I've made lots of dumb decisions. That's part of the game."

Horowitz says CEOs need courage: to make decisions even when they're unsure, and to make the correct decision even when it's not the popular one. Fortunately, courage can be developed. "Every time you make the hard, correct decision," Horowitz says, "you become a bit more courageous."

In my case, I decided to make the potentially unpopular decision to discontinue the collaboration. Was it the right decision? Time will tell.

The ability to be comfortable with taking calculated risks is precisely what sets CEOs apart from other executives. The more you do it, the more comfortable and the more courageous you'll get.