“Raise It Early”
Needs Answers Your Team Can Look Up.

Your team is moving its customer records to a new system, and the go-live date is set. One morning, someone on your team tells you the vendor is a week behind. You already knew, so you thank them and say kindly, “We knew about that one.”

A few weeks later, the same person mentions that some customer records went missing in a test run. They saw it when the go-live was still five weeks away. It is now three weeks away, and moving it this late means paying a penalty.

When you ask about the timing, they say, “I thought you knew.” You may assume your own boss already knows, too, and an executive team may assume the same of its board. For each decision your team makes again and again, you can end the guessing by writing down how much notice you need and what you already know.

Anyone who has led a team has said some version of “Raise it early, no surprises.” I give it real credit, because it taught every team that bad news costs more the later it arrives. On a team that has worked together long enough, people do learn what their leader needs to hear.

In their 1980 article “Managing Your Boss,” John Gabarro and John Kotter rightly made it each person’s job to find out which problems their boss wants to hear about, and when. What I would add is that you, the one making the call, write those answers down, once for each decision your team makes again and again.

“Raise it early, no surprises” leaves three things out: what counts as early for each decision, what you already know, and what would surprise you. Your people have to guess all three from your reactions, and getting them right can take years. They raise something and hear “we knew,” so they raise fewer risks. Then a risk they held back turns out to matter, and someone asks why nobody said anything.

People learn those three things in one of two ways, and both ways can get them right. Some pick them up by intuition, from how you react. Others work them out on purpose, step by step. I am autistic and work them out that way, and it takes me real effort.

Either way, your people are doing work you could do once, in writing. That guessing is what I mean by cognitive load, and your organization pays for every hour of it.

When your organization sets up an alert on a system, such as a budget tracker or an AI tool that flags unusual invoices, someone decides in advance what should trigger it. The same organization gave the people on your team one sentence, “Raise it early, no surprises.”

So take each decision your team makes again and again, such as whether the go-live date still holds each week. Write two lines for it once, at the top of your team’s risk list or wherever your team tracks the work. The first says how much notice you need to change course, which is what early means for that decision. The second says what you already know and what would surprise you.

For your go-live, the two lines might read like this:

Under the two lines, write the name of the one person who checks each new risk against them, such as your project lead. When a new risk would surprise you, or leaves less notice than you need, that person tells you the same day.

That step comes from my Decision Charter, which my earlier essays called DecisionOS. In it, reading the risks and making the call are two jobs, because the person with the clearest view of a risk is rarely the person who decides.

With those two lines written down, your people can look up what counts as early instead of learning it from a “we knew.” The second line says what you already know, so nobody has to say “I thought you knew.” Your people can spend their attention on the risk itself. The next time a test run loses customer records, they know to tell you while you can still move the date.

Follow this rule: one named person reads the risks and can be asked to explain them, and another person decides. Decision: [decision]. Who reads the risks: [role]. Who decides: [role]. Risks we track: [list]. Safeguards we have today: [list]. First, help me write two lines: how much notice the person deciding needs to change course, and what they already know and what would surprise them. Next, for each risk, say how big it is before any safeguards, which safeguards actually work and how we know, and what is left. Then list what is changing outside our organization (the vendor, customers, rules), then inside it (people, budget, deadlines), that could change what is left. Mark which risks the person deciding already knows and which would surprise them. Show me your reading and the open questions, and leave which risks matter to me. If you do not know something, ask me instead of guessing. If the same person reads the risks and decides, say so.