Unless someone is spectacularly inept, there’s always a reasonable sounding explanation for why the project they were involved with fell short. Maybe the direction was unclear, maybe the technology was harder than expected, maybe it was just too ambitious.
It’s sound and human to be sympathetic to such woes, even if you think things should have gone better or faster or made more of an impact. But at some point, you have to decide whether you’re judging someone’s work merely on their earnest effort or whether it’s by the results (or lack thereof).
To me, that’s the dividing line between someone able to lead a team executing a vision, and someone who’s simply on a team working to a plan. I can’t fault someone who’ve done their part well if the whole thing falters, unless their part was the responsibility of the whole thing.
It’s in this executive leap where judgement is rendered as much on all the things you did, as on all the things you didn’t do. If you’re leading the charge, almost everything that happens could have happened differently by the weight of your choices. You have to accept that if you want to play the lead part.
This negative space, the actions not taken, is carried on confidence. Can you maintain that confidence? Can you build it? If not, soon nothing else matters. You can’t be effective without confidence. That’s the whole buck-stops-here premise.
The hardest part is just how fuzzy that evaluation can be. What does it actually mean to “lose confidence”? It’s usually a build up of so many little things, then the final snowflake that bends the leaf of the bamboo.
The problem is that most creative, entrepreneurial work can’t be examined as a closed system. You don’t get to hold all other variables stable while you examine just the one. Which means conclusions can only be drawn from the whole, fuzzy picture.
Being a leader means accepting such uncertainty, and making or accepting the most compelling choice regardless.