One of the few people I have respect for in my career had a phase for this regarding the progress of projects, and I think it applies to start-ups in the sense

One of the few people I have respect for in my career had a phase for this regarding the progress of projects, and I think it applies to start-ups in the sense that sometimes people are blinkered about what they are doing and that is this: "Disappoint early" In other words, as soon as you are aware of a problem - Raise it. And then discuss it and work it out.