The core problem is that most people either bury their manager in irrelevant details or leave out critical information, forcing follow-up questions that slow everything down. Wes Kao breaks this into practical moves: remind your manager where you left off so they don't have to context-switch from scratch, be explicit about what you need from them rather than leaving it ambiguous, and clearly mark whether something is just FYI or requires action. The real skill is distinguishing between details that matter and details that add noise. If you're telling someone a customer got fewer signups in cohort two because the enrollment period was shorter, you don't need exact dates—just the fact that they had six weeks the first time and one week the second time. Too many numbers and specifics actually make people work harder to figure out what's important. The variables that determine how much context you should give are straightforward: spend more time explaining when money's involved, when it's customer-facing, or when you're making a decision type you've never handled before. Spend less when you and your manager have done this a hundred times, when the decision is cheap to reverse, or when it's already top of mind for them. One underrated move is showing your work—mention the criteria you used to evaluate options and flag your assumptions. This lets your manager catch flawed logic early or add relevant information you missed, rather than having to reverse-engineer your thinking. The takeaway isn't about being brief for brevity's sake. It's about matching the detail level to what your audience actually needs to make a decision or understand where you're headed. High performers get this right because they think about cognitive load—every unnecessary detail forces their manager to mentally sort what matters from what doesn't. In remote work especially, where you can't just swing by someone's desk, nailing this skill is what separates people who move teams forward from people who create friction.