This timely post, that I stole the title from, by Matt Blumberg took the words, in a timely manner no less, right out of my mouth. I'm seeking inspiration from Matt (unbeknownst to him) to get some of my "first time CEO" challenges out on paper for therapeutic purposes.
Gnip has grown a lot/fast over the past year or so. I've, idealistically, and at times detrimentally, carried beliefs and values near and dear to me through that growth, thinking they can scale without modification. Some of them scale just fine (e.g. honesty). Some of them don't scale as well.
In a smaller team (say ~12 or less) you're all relatively close in proximity, and in thought/conversation, on a day-to-day basis. As a result, there's a general sense of understanding of most topics across the organization. Joe can see Jane's frustration level when she's moving through a challenge. Mark has an ambient sense of how Jenny can power through technical challenges of certain shapes and sizes.
When you move past ~12 people on the team, individuals simply have to compartmentalize more of their thinking, and must drop certain levels/depths of awareness in order to stay productive. The result is less overall context and understanding of everyone else's headspace. To drive the point home, here's an extreme example (something I love to provide, which I'm also learning isn't as effective as the team scales). If your good friend says to you "let's go have some fun," you probably have a decent sense of what that means. If someone less familiar to you says the same thing, you have no idea what that statement means to them. In both cases, the other party was being fully transparent about what they want to do, but without the right context, the latter can leave you dangling. As the team grows, that ambient contextual awareness changes.
As we've grown, it's become clear to me (through direct feedback, and my own observation) that the off-the-cuff transparency I've always enjoyed with my thinking and thought process, can actually be damaging. What I would consider a transparent comment about a certain direction I think we should be going in can be interpreted many was, with many unintended consequences. Matt nails it with the "the CEO said" or the "CEO thinks" points he makes. That stuff can be disruptive, confusing, and derailing.
The result is that more preprocessing (natural for some, unnatural for others; somewhere in-between for me I think) and better awareness of one's surroundings is required. That, to me, can feel less transparent, and my initial reaction to that has been that it is bad. It's required to function however, and therefore I wind up in a place where I view it simply as adaptation to environmental changes.