When to Escalate and When Escalating Makes You Look Worse

Early in my career, I escalated too readily, every blocker, disagreement, straight up the chain, because I'd been taught that transparency meant surfacing everything immediately. What I actually taught my stakeholders was that my escalations weren't a reliable signal of real severity, and by the time something genuinely serious came up, they'd stopped reacting with urgency.

The opposite mistake is just as costly and more common among experienced PMs who've learned to be cautious about crying wolf: sitting on a real problem too long, trying to solve it quietly, because escalating feels like admitting you couldn't handle it yourself. By the time it surfaces, the options for fixing it are far more limited than they would have been two weeks earlier.

The test I now use before escalating anything: have I already tried the two or three things within my own authority to resolve this, and is the outcome I need genuinely outside my control to influence? If I haven't tried what's within my power yet, it's not ready to escalate, it's ready to work. If it is genuinely outside my control, sitting on it doesn't protect anyone; it just delays the moment someone with the right authority can act.

How you escalate matters as much as when. An escalation framed as 'I need help making a decision' lands completely differently than one framed as 'this is broken and I don't know what to do.' The first signals judgment under pressure. The second signals the opposite, even when the underlying situation is identical.

Good escalation isn't about frequency in either direction, it's about calibration. Save it for the moments that genuinely need someone else's authority, bring options rather than just the problem when you can, and your escalations will carry real weight exactly when you need them to.