This is an incredibly brave and insightful post by Erin Chan that I think every product manager should read. In The Hard Thing About Complex Products & How I’ve Grown as a PM she describes a long, failed project at Shopify in detail, and what she learned. The section on creating “tripwires” for complex projects is something I’m going to start using immediately:

A tripwire is a mechanism or an indicator that you define, and when it gets triggered, flags are raised.

For example, you should set the tripwire of ‘time’ when a milestone isn’t completed after a defined period (for me, this should have been two months). When that happens, my recommendation is to have a serious discussion with the team and make your Leadership and stakeholders aware of what is happening. Communicate the changes that you will make to the team or process to get the project back on track. Next, outline what happens if the milestone isn’t completed in three months, then four. These are your tripwires as determined by time, but you can define tripwires in whatever form you see fit for your initiative.