Skyler Rogers

One of the most interesting metrics of company culture is what I call the "work to do the work." How much time is spent on information gathering, stakeholder alignment and decision making, and how much is spent on actually doing the thing. An early startup's biggest advantage is that alignment tends be easy, since you have a small team all working on the same product, a founder who is the ultimate decision maker, and a necessary bias to action (maybe a 1:10 WTDTW:W ratio). As you scale, this ratio invariably shifts: bigger teams, more hierarchy, more complexity, more feedback to inform future decisions. Good processes should be in service of helping teams make and communicate well-informed decisions so they can still spend the bulk of their time actually moving things forward. The problem with a high WTDTW ratio isn't just that it slows teams and companies way down, but that it changes the incentives of an organization. In a company with a 10:1 ratio, for example, employees are rewarded for their ability to navigate and influence the organization, rather than producing results. I distinctly remember a moment in my career when I realized, with horror, that I was pouring the vast majority of my creative energy into solving problems in the WTDTW realm (and getting real personal satisfaction from playing that role well)...but I was exhausted by the time we actually got to execute. And it's a dangerous trap, especially for executives, to think that all the "strategy" is in the WTDTW bucket, because the creativity, iteration and debate that goes into actually bringing something to life is where the magic happens, whatever your company's size. 🪄