Context

I recently completed a complex (Agency) migration project. Initially, the project was framed as a small-scope effort, but once I began, I discovered significant gaps and unmapped dependencies with no clear owners due to recent organizational shifts.

The volume of gaps made it impossible to manage alongside my other responsibilities. When initial attempts to get support from my direct manager didn’t yield results and the risk of delay became critical, I made the decision to escalate to my skip-level manager. This move finally brought the necessary attention to the project, resulting in my manager and two L6 engineers being assigned to prioritize and finish the work.

Key Learnings

Watching how senior leaders stepped in provided a masterclass in high-stakes project management. Here are the lessons I’ve taken away:

1. The Necessity of Escalation

One of the biggest lessons was realizing that escalation is a tool, not a failure. When there is a high risk of project delay that cannot be resolved at your current level, you have a responsibility to surface it. Staying silent while a project fails is much worse than the temporary discomfort of escalating.

2. Maximize “Legal” Channels

While skip-level escalation was necessary here, I learned that communication should happen through established “legal” channels as much as possible to avoid surprises. The weekly report I maintain is my most powerful official channel—I realized I need to use it to flag risks more clearly and frequently before they require a direct skip-level intervention.

3. Earn Your Seat at the Table

If you aren’t being given the space to speak or provide input, don’t wait for an invitation. Find the chance to speak. Once you start providing valuable insights or identifying critical risks, you’ll find that people not only start listening but will actively invite you to the decision-making meetings.

4. Formalize the Chaos

Visibility is the first step toward resolution.

• Create Bugs: Don’t just talk about problems; file bugs for every important issue.
• Write it Down: Create concise documents that outline the gaps and their impact.
• Share Widely: When problems are documented and shared, they become visible to everyone, making it much easier for leadership to prioritize them.

5. Use Process as a Tool

When a project is at risk, communication needs a dedicated rhythm.

• Leverage TPMs: Work with Technical Program Managers to bring structure to the communication.
• Dedicated Syncs: Schedule specific meetings or use calendar placeholders to ensure the situation is communicated clearly to all stakeholders. Don’t assume everyone understands the risk—make it undeniable.