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 giving challenging news, leaders cannot just "drop the bombshell and walk out." A successful approach requires three steps: 1) be clear and direct with the news, 2) provide the context and rationale behind it, and 3) stay to connect with the team, showing commitment and outlining next steps.

To manage investor expectations effectively, adopt a contrarian communication cadence. Only report good news (like a major deal) after it has officially closed, since many B2B deals fall through at the last minute. Conversely, report bad news as early as possible. This builds trust by preventing over-promising and demonstrating transparency when it matters most.

The 'fake press release' is a useful vision-setting tool, but a 'pre-mortem' is more tactical. It involves writing out two scenarios before a project starts: one detailing exactly *why* it succeeded (e.g., team structure, metrics alignment) and another detailing *why* it failed. This forces a proactive discussion of process and risks, not just the desired outcome.

Even with a solid plan, failing to communicate it *before* execution makes you seem reactive. Leaders perceive strategy through proactive announcements. Stating what you are going to do frames your actions as deliberate, while explaining them only when asked sounds defensive and tactical.

Don't be afraid to surface problems to executives, as their job is almost entirely focused on what's not working. Withholding a problem is unhelpful; clarifying and framing it is incredibly valuable. Your champion isn't offending their boss by raising an issue, they're demonstrating strategic awareness.

Leaders often avoid sharing negative news to "not scare the children." However, this creates an information vacuum that teams will fill with the "darkest ideas available" from other sources. Leaders must compete with misinformation by providing clear, honest context, even when it's difficult.

Before starting a project, ask the team to imagine it has failed and write a story explaining why. This exercise in 'time travel' bypasses optimism bias and surfaces critical operational risks, resource gaps, and flawed assumptions that would otherwise be missed until it's too late.

When progress on a complex initiative stalls with middle management, don't hesitate to escalate to senior leadership. A brief, well-prepared C-level discussion can cut through uncertainty, validate importance, and accelerate alignment across teams or with external partners.