What Got You Here Won’t Get You There

By this point, everyone knows the classic story of the garage-based startup. Whether it's Hewlett-Packard, Apple Computer, or your neighbor Larry's custom bobblehead business, there are tons of these stories. My own grandfather started a family business in the family basement that outlived him (and put me through college). These stories are great because they show us how to start small with just a handful of people yet see your endeavors reach life-changing heights. One thing I'd wager all those stories have in common: the way these folks worked in the garage is different from how they worked when they moved into their first dedicated space (not to mention their apex).

While your business might not have started in a literal garage, you probably worked the same way with your early team. With just a handful of employees, communication is easy. Maintaining context and state is achievable with ad hoc methods and just what feels right. Humans have several tens of thousands of years of experience working together in small groups. We do it well, even when using modern tools.

The issue is when we start exceeding those natural boundaries and try to juggle too many contexts and relationships. You start to spend more time maintaining state than actually doing work. Your teams—who used to have a firm grasp on everything—start to lose track of what needs doing, where things are, or who said what when. You might stave this off a little while longer by adding a few tools or services, but that's addressing a symptom, not the underlying condition.

This isn't an indictment of you or your employees' ability. It's simply a function of scale. Your company might have moved out of the metaphorical garage a long time ago, but what about your digital operations? These are signs that you need to step back and evaluate how you're working.


I help growing organizations remove blockers to collaboration and scale. I’ve built flexible structures for my own teams and helped many others do the same, from small startups to Fortune 50 goliaths. What are you and your team experiencing? Let's talk.

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