To move beyond status updates in one-on-one meetings, managers should open up about their own challenges. Asking a team member for their perspective on a decision the manager is making fosters trust, shows respect, and can uncover valuable insights you hadn't considered.

Believing traditional weekly 1-on-1s are inefficient and repetitive, V0's leader eliminated them. He favors discussing shared topics in group settings (like a Slack huddle) and reserves direct 1-on-1 time for specific situations like onboarding, rather than a fixed weekly cadence.

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.

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.

Go beyond visual roadmaps. Create a monthly written document for executives that explains *why* the roadmap changed, details priorities, and includes data from recent launches. This forces intentionality, builds trust, and fosters deeper, more accountable conversations with leadership.

Most managers default to using 1-on-1s as pipeline reviews. This is a mistake. Dedicate separate meetings for deals (Deal Reviews) and protect the 1-on-1 as a "sacred space" for building connection, discussing personal and professional development, and strengthening the manager-rep relationship.

When meeting with senior leaders, shift the focus from your status updates to their priorities. Ask what's top of mind for them, what challenges they face, and how you can help. This reframes you from a direct report into a strategic ally, building trust and social capital.

Leaders often assume goal alignment. A simple exercise is to ask each team member to articulate the project's goal in their own words. The resulting variety in answers immediately highlights where alignment is needed before work begins, preventing wasted effort on divergent paths.

CPC separates board meetings into two sessions: a virtual one for reviewing past results with functional leaders, and a subsequent in-person meeting for forward-looking strategy with the CEO. This structure prevents the common trap of getting bogged down in past performance when strategic, future-focused discussion is needed.