To avoid appearing incompetent, frame conversations with your manager around validation, not direction-seeking. Present your understanding of the goal, your proposed plan, and your key assumptions. This demonstrates proactivity and critical thinking while still inviting feedback.
Working in isolation without providing updates puts your leader in a vulnerable position. When they can't answer questions about your progress, they appear uninformed to their own superiors, which severely damages the trust they have in you.
Leaders set direction from a strategic vantage point but lack visibility into on-the-ground realities. It is your responsibility as an individual contributor to proactively communicate unforeseen challenges and propose better paths based on what you encounter directly.
When working under a less-experienced manager, you must take the lead in defining the relationship. Proactively push for clear goals, establish a check-in cadence, and ask for the feedback you need. In essence, you are teaching them how to be the manager you require.
Surprising your manager with a major failure is one of the worst mistakes you can make. You must proactively communicate risks as soon as they arise. This gives your leader time to manage expectations up the chain and prevents them from being blindsided.
Many 1-on-1s become rote reviews of past work. A more effective approach is to dedicate significant time to discussing future plans. Use this opportunity to check in on upcoming goals and direction, ensuring you and your manager are aligned before work begins.
Ignoring a request from your skip-level manager isn't an option, even if your direct boss disagrees. The correct strategy is to find the most efficient, minimalist way to fulfill their request. This maintains your credibility without derailing your primary, manager-aligned objectives.
When sharing progress with other teams, say "My boss and I have been working on..." instead of "I've been working on...". This approach gives your manager credit, avoids triggering their insecurities, prevents you from looking like you're circumventing them, and builds political capital.