Voluntary Complexity

Right around the addition of the 50th person, something often goes awry in a startup company.  Between 30 and 50 people, I’ve seen it happen that the group loses the ability to feel like one team – to cluster in a room or a Slack channel and include everyone in the conversation.  Teams and roles become more divided, and just around 50 people a threshold effect happens.  Not everyone knows what decisions are being made any more.  The “why” of a decision becomes something harder to discover.  And all of a sudden, every piece of information comes with an invisible tax of figuring out who needs to know.   

What can happen at this point is that the self-directed, fast-moving engineering team can become a little less certain of what they’re doing. Each person is still doing roughly the same thing but with less ability to see how it fits into the whole.  And from the top, it becomes much harder to see the details of the decisions being made and why people are doing what they’re doing. 

At this point, there’s still all the start up energy, the intelligence and enthusiasm for the mission, the desire to do something excellent together, but suddenly it can become hard to trust that we are all doing the right things. Compared to the “good old days”, an immense amount of energy flows into internal communications.  

I’ve seen organizations stumble at this point by putting in damaging amounts of process but it seems to me that the right path is to refrain from controlling the details of every leaf of the tree.  Rather, build the structures and cadences of communication that allow people to discover for themselves where their particular contribution and talent fits into the big picture. The roadmap becomes a guiding document internally, and perhaps for the first time, so does the org chart. 

One management tool that becomes more important is process documentation, not to be a straitjacket but to help inform and socialize, this is how we do things here. The patterns you’ve chosen for development and deployment, for handling customer problems, for when and whether to publish information, and others, reflect the values and core concerns of the organization. The more they’re shared, the more the detailed decisions can be trusted to be the right brushstrokes to paint the picture – and the more all the new people that your startup would like to include can join in and make quick and independent decisions with confidence that they’re doing the right thing.