Escalate, Absorb, Flag

Earlier in my management career, I was an over-escalator. I escalated constantly. I’d like to formally apologize to my former director.

I thought I was doing exactly what good managers were supposed to do. I was keeping my director informed. If there was even a chance something might become important, I made sure they knew.

I wasn't wrong, but I also wasn't right. Most importantly, I wasn’t making their job easier.

Ultimately leaders don't just need information from their direct reports. They need judgment.

My director wasn't looking for a human notification system. They needed someone who could process ambiguity, solve what was solvable, and involve them at the right moment.

Though not my personal brand, I’ve also witnessed the other end of the spectrum - what I will for lack of a better name call the absorber. This is the person who gets reasonably capable and starts handling everything on their own. Even things way beyond what they could reasonably solve themselves. Nothing gets bubbled up to their manager or someone more senior in part because they’re afraid that saying there was an issue they didn’t solve means they weren’t capable or were somehow lacking. 

Most leaders hate surprises. Absorbing too much information creates them. 

There's a third category that sits between escalating and absorbing. I call it flagging. You reach out to your leaders and say here’s the problem and here’s what I’m doing about it. Here’s what I need from you (if anything). Flagging gives your manager context before they need to ask for it. If everything goes according to the plan you laid out, they already knew about the risk and saw you handle it. If things go sideways, they aren't learning about the problem for the first time in the middle of a crisis. Remember: no surprises!

The difference between flagging and escalating is ownership. When you escalate, you're asking someone else to own the problem or make the decision. When you flag, ownership stays with you. Awareness expands but you’re not handing off ownership of the problem. The added benefit of this approach is that it makes your work visible. All that effort you’re putting into problem solving is suddenly additional credibility building your reputation. Leadership sees the problem and sees you handling it. 

Imagine that I received two slack messages from engineers on my team. One message reads: "There's a dependency on Team B." And the message other reads: "There's a dependency on Team B. I've already reached out to them and we have a meeting tomorrow. If they can't commit by Friday, we'll need to talk about de-scoping Feature X."

If you were in my shoes which engineer would you consider more senior? Which engineer would you trust more? Probably the second engineer, and not because one has fewer problems than the other, but because one has demonstrated ownership. 

When a person thinks they're saying, "I have a problem." The manager hears: "I'm handing you a problem." Those aren't the same message. On more than one occasion I’ve compared managers to beavers. If a beaver hears running water they’re compelled to try and dam it. If a manager hears of a problem without a clear solution they’re going to try to solve it. By including what you're doing about a risk, the message becomes: "I have identified a risk and I'm actively managing it." That's an entirely different signal.

Every leader has different preferences, but the principle stays the same: communicate in a way that increases visibility without unnecessarily transferring ownership.

It’s not always easy to know which approach to take. Becoming more senior in your role doesn’t mean flagging is the right solution every time. But with enough exposure to problem solving, eventually you develop an instinct for which situations require which response. Some risks should automatically be escalated because they're high risk, irreversible, or outside your authority to decide. Some risks are simply part of your job - you can handle them and move on. Most risks live somewhere in the murky middle. In those cases it’s generally beneficial to flag them because leadership needs visibility into what's happening while trusting you to keep driving.

My standard gravitates towards: escalate when ownership needs to move, flag when ownership stays with you, and handle it yourself when you can resolve an issue and move on.

The goal isn't just to minimize what lands on your leader's plate. It’s to become someone your leaders trust with hard problems because you know the difference between solving them in a black box and communicating them upward.

While I am no longer the new manager escalating everything, I do look back on her fondly. She just needed a minute to figure out that what her leaders wanted from her wasn’t just communication, but judgment.