The more I dive into researching best practices for building and running remote teams, the more I'm starting to realize how valuable the experience of running Orbital and evolving the Entrepreneurial Design course has been.

Both presented challenges that were very difficult to hide from.  When you're dealing with end users who are right in the room with you, you have to adjust, compromise, and confront the truth regarding whether your approach is or isn't working.  And, you have to learn how to process the immense qualitative data, the tone of people's voices, their body language, the power dynamics as a part of that.  And further, you have to learn when to distance yourself from your own experience in the room, and when to rely upon that.

Despite a career of working on software product management, it was clear that I needed the training.  This is a different environment altogether compared to building an app, where you're looking at quantitative metrics, cleaner data, to assess whether what you have is working.  That you aren't an actor in the system, either, allows you the convenience of knowing that the decisions you make don't necessarily impact your day-to-day in the same way that it may impact your end users.

Unfortunately, this privilege doesn't extend to you when you're designing how your company operates.  There, you have to face the fact that you can't hide from the impact of your design decisions–the org structure, the rituals, the policies, the goals–because you are clearly in control of changing them.

Like any design process, it's challenging because acknowledging the success or failure of a decision takes a personal toll.  There is an immense emotional energy cost to these things.  And over time, only through practice, will you learn how to manage this.  And for that reason, one of the most important design decisions you can make is ensuring that you will have sufficient time to make the mistakes that you need to make in the first place, before you run out of time and capital.