Proactive leadership sounds straightforward. Here’s why the incentive structure works against it — and what it takes to change that.
I’ve sat in a lot of status meetings where the room wasn’t really in the room.
Leaders multitasking. Half-attention on the slide, half somewhere else. Risks documented, bubbled up, noted in the status email that went to the right distribution list. The process worked exactly as designed. The signal was observed, communicated, and received — technically. Then something breaks and the questions start. Why didn’t I know about this? You should have made sure I was more aware.
And there it is. The accountability transfers from the person who didn’t receive the signal to the person who sent it. We told you. In the meeting. In the email. In the status. That’s the losing argument, even when it’s true.
The Signal Was There
This is worth sitting with, because it’s easy to read this as a leadership failure and stop there. It’s more complicated than that.
The information existed. The risk was documented. The communication happened. By every formal measure, the organization did what it was supposed to do. The signal was in the system.
But the signal was in our language, not theirs. We led with the technical risk, the process concern, the architectural debt. We expected the decision maker to translate that into their own terms — to connect the signal to the metric it would eventually impact and decide whether to act.
That’s not their job. It’s ours.
I spent a long time trying to convince decision makers in my own way, with what I thought was important, communicated the way I thought it should be communicated. The frustration when they didn’t respond felt justified. But it was misplaced. It wasn’t about me, or my argument, or the quality of the data. It was about whether I’d connected the signal to something they were already watching.
That’s failure mode one. And it’s on us to fix it.
The Signal Was There and It Didn’t Matter
Failure mode two is harder, because it doesn’t have a personal fix.
Even when the connection to the metric is made clearly — even when you’ve done the work to translate the risk into their language and show them what it will cost when it lands — if the metric isn’t hurting yet, the signal still loses the priority battle. The urgency isn’t there. There are other fires already burning, other things costing them something today rather than something they’d have to imagine.
Future-tense risk is always competing against present-tense urgency. And present-tense urgency wins almost every time.
I watched this play out at a company I worked for earlier in my career. Warning signs that a platform wasn’t scaling properly. The data was there. The analysis was done. The flags were raised. The response was essentially: we see it, we’ll deal with it, it’s not breaking anything yet. Until it was. The failure spread faster than anyone had planned for, the recovery was harder than it needed to be, and customers felt it in ways that could have been smaller or avoided.
That’s not a communication failure. That’s a structural one.
Know Your Audience
The practical lesson from failure mode one — the one I learned the hard way — is simple to say and harder to do consistently.
Lead with the metric. Not the technical risk, not the process concern, not the backstory. The number. The thing they’re already watching. Show them what happens to that number if the risk materializes, and when.
The quality of your argument in your own terms is irrelevant if it doesn’t connect to theirs.
Every decision maker has a set of incentives they’re optimizing for. Your job, when you need a decision, is to understand those incentives and use them to frame the choice. Show me the incentive and I’ll show you the outcome — that applies to the person you’re trying to persuade as much as it applies to the market.
The frustration of learning this is real. There’s something that feels like a concession in it — like the data should be enough, the risk should be obvious, the right thing to do should be self-evident. It isn’t. The person who learns to speak the language of the people making decisions gets heard. The person who keeps communicating in their own language keeps getting frustrated.
What This Can’t Fix
Failure mode one is solvable. Better communication discipline, more deliberate connection of signals to metrics, more investment in understanding what the decision maker is watching. Teams can get better at it.
Failure mode two is different. Even with perfect communication, risks that don’t impact a current metric still lose. Prevention doesn’t have a metric.
Nobody gets credit for the fire that didn’t start.
The fire that never started doesn’t show up in the quarterly review. The only thing that changes that is when the organization decides to measure it. When preventing the fire becomes something someone is accountable for. When the proactive decision gets credited for what it avoided rather than penalized for what it cost.
Most organizations don’t do that until the fire forces them to.
The Direction Worth Moving In
If we can get better at failure mode one — close the communication gap, build the language, show through data that proactive decisions compound better than reactive ones — we earn something more valuable than avoided crises. We earn credibility. And credibility is what opens the door to the harder conversation.
The harder conversation isn’t about this project or this risk. It’s about whether the metrics themselves are right. Whether the incentives the organization is optimizing for are the ones that produce the future it says it wants. The same discipline that connects a technical risk to a business metric can connect a business metric to a longer-term outcome. If you’ve built enough trust by being right about the near-term things, you get a hearing on the longer-term ones.
That’s the direction. Reactive to proactive. And then, proactive about what we’re actually optimizing for.
Right now, inside most organizations, the fire is still what gets attention.
The goal is to change that before the fire starts.