I've consistently underestimated how important communication is as a CEO

We take pride in investing as much as possible in our ability to ship cool projects and not in hiring a gazillion managers. As a result, we only have an exec (AKA blitzscale) team of 5, with roughly 150 people working here. And that includes Tim and me as half of this team. Everyone else is doing a ton of individual contributor work.

As we've grown, I've repeatedly underestimated how sharply the importance of communication from the exec team increases. I up the effort, but the requirement ups by more each time we grow, despite knowing it's important. I've even had feedback in 360 reviews of "if you did nothing else, just do a good job of the all-hands and that'd be great".

The number of people each exec is responsible for is increasing exponentially as we scale. In the early days, we had zero direct or indirect reports each, at 15 people, we had roughly 8 people per exec. Today, it's around 35. By the next big offsite, it will be around 80.

There are unfortunate consequences of this:

• Less communication is felt
• It seems more out of the blue
• Everyone thinks it has come from "more DMs".

This can make things seem disjointed. The reality is — we've kept up about the same level of public communication, and really don't suddenly hold lots of secret meetings, but the team or individual level comms are now further removed from an "unrelated" employee (since you can't be buddies with 149 other people), who is more likely as a result to be blindsided by a change we've decided to make. That doesn't feel good for anyone.

Not knowing everything that is happening

When we're tiny, it's very easy for each exec to know, and be involved in, pretty much everything that is happening. At our current scale, there is too much for one person to hold it all in their head at a meaningful level of depth. Some people are better at this than others.

Seeing this, the way we've divided the work is based on skills — Raquel, Charles, and Ben on the exec team are exceptionally good at handling a larger number of people and projects. Tim and I are better at things that need to go from 0 to 1. This has worked well for the four of us, each enjoying their role and being good at it.

One of the mistakes I think I have been making is talking in all-hands mostly about the projects I am focused on (a lot of AI). However, this doesn't reflect the bulk of the daily work at the company. The other stuff does greatly matter but I've not felt like an expert in it.

Clarity vs transparency

It feels easier to make a mess inside a bigger company — it's pretty easy to just chuck 3 other people on a call and hash out something if things get messy, since everyone has all the context. At 150, you can't do that.

I've tried to be a little clearer when I communicate because of this. However, that often means less communication (it takes time to make things more polished) and it is less transparent — I'm not sharing half baked thoughts quite so much.

Tim and I think we should share these ideas a little earlier, and in a way that solicits feedback — we think we've tried too hard to be polished, and frankly to make changes "quickly" without lots of committees and consensus, which is creating too much "top down" communication and not making us quicker as a result.

So, what are you going to do about it?

Ok, hypothetical h2 tag voice, there is a solution.

I will balance the content of the all-hands more. If I don't have the depth to really nail a topic, I will get other people involved.

When we have big ideas for changes, we'll solicit feedback on them when they're not 100% watertight as ideas. We'll reduce the level of polish and increase the level of transparency (and mess, at times).

Beyond that, a little more time on communication is likely worth it. That doesn't mean more meetings, it means a reminder to myself mostly to write down thoughts and to share them publicly. Like this one.