Every layer of management compresses information. By the time a problem on the front line reaches a founder or executive, it has been through one or two rounds of "let me see how to frame this." That is not malice; it is the natural compression of bad news travelling upward. The result is that leaders consistently overestimate how well things are going.
The cheapest fix
Talk to people two levels below you, regularly, in unscripted settings. Not skip-level surveys, not engagement scores, but actual conversations with engineers, support reps, account managers, anyone close to the work. You are not bypassing your managers; you are calibrating your model of reality.
What to actually ask
Forget "how is it going." Ask: what would you change if you had a magic wand for one day? What is the most frustrating part of your week? What is the thing nobody is talking about that everyone knows is broken? Then listen, do not defend.
What to do with what you hear
Almost nothing immediately. The point is calibration, not action. Patterns across many conversations are the signal; one-off frustrations are noise. Over months, the picture you build is more accurate than any dashboard your leadership team produces.