Asking yourself, “Do I value internal or external knowledge more for this position?” will help you determine whether to go for experience or youth. - Ben Horowitz

The very best way to know what you want is to act in the role. Not just in title, but in real action. In my career, I’ve been acting VP of HR, CFO, and VP of sales. Often CEOs resist acting in functional roles, because they worry that they lack the appropriate knowledge. This worry is precisely why you should act — to get the appropriate knowledge. Indeed, acting is really the only way to get all the knowledge that you need to make the hire, because you are looking for the right executive for your company today, not a generic executive.

As we thought about what would make us both better and different, two core ideas greatly influenced our thinking: First, technical founders are the best people to run technology companies. All of the long-lasting technology companies that we admired — Hewlett-Packard, Intel, Amazon, Apple, Google, Facebook — had been run by their founders. More specifically, the innovator was running the company. Second, it was incredibly difficult for technical founders to learn to become CEOs while building their companies. I was a testament to that. But, most venture capital firms were better designed to replace the founder than to help the founder grow and succeed. Marc and I thought that if we created a firm specifically designed to help technical founders run their own companies, we could develop a reputation and a brand that might vault us into the top tier of venture capital firms despite having no track record. We identified two key deficits that a founder CEO had when compared with a professional CEO: 1. The CEO skill set Managing executives, organizational design, running sales organizations and the like were all important skills that technical founders lacked. 2. The CEO network Professional CEOs knew lots of executives, potential customers and partners, people in the press, investors, and other important business connections. Technical founders, on the other hand, knew some good engineers and how to program.

A good culture is like the old RIP routing protocol: Bad news travels fast; good news travels slow. If you investigate companies that have failed, you will find that many employees knew about the fatal issues long before those issues killed the company. If the employees knew about the deadly problems, why didn’t they say something? Too often the answer is that the company culture discouraged the spread of bad news, so the knowledge lay dormant until it was too late to act. A healthy company culture encourages people to share bad news. A company that discusses its problems freely and openly can quickly solve them. A company that covers up its problems frustrates everyone involved. The resulting action item for CEOs: Build a culture that rewards — not punishes — people for getting problems into the open where they can be solved.