“I Thought You Knew”
Is How Risks Reach You Late.

When did you last hear "I thought you knew"?

It goes like this. Someone on your team brings you a risk. It's real, and it matters. But the deadline is close now, and most of your options are gone. So you ask them how long they've known. A few weeks, they tell you. And then they say it. "I thought you knew."

They guessed that you already knew, and the guess was wrong. You might make that same guess about your own boss, and an executive team might make it about its board. That's what this episode is about. "I thought you knew" is how risks reach you late.

There's a second half to it. Someone brings you a risk you already knew about. You thank them, and you say, kindly, "We knew about that one." And what they learn from that is to bring you fewer. Next time, they hold it back.

Put those two halves together. Everyone on your team is guessing about what you already know.

This season, in each episode I take one piece of advice every leader already gives, and I give you one skill that ends the guessing inside it.

So here's the advice. "Raise it early, no surprises." Anyone who's led a team has said some version of it, right? I give it real credit. Because of it, every team learned that bad news costs more the later you hear it. And on a team that's worked together long enough, people do learn what their leader needs to hear.

In 1980, John Gabarro and John Kotter wrote an article called "Managing Your Boss," and they rightly made it each person's job to find out which problems their boss wants to hear about, and when. What I'd add is who writes those answers down. You do, because you're the one making the call. You write them down once for each decision that keeps coming back.

Now, that one sentence on its own, "raise it early, no surprises," leaves three things out.

The first is what counts as early. Early depends on the decision. Moving a launch date might need a month's notice. Moving an internal review might only need a day. So your people have to guess which.

The second is what you already know. Your people can't see what's already reached you, so they guess.

The third is what would surprise you. That often depends on history, on things that happened before some of your people even joined. So they guess that too.

And then one day, a risk somebody held back turns out to matter, and someone asks why nobody said anything. Learning all three the hard way can take years.

People learn those three things by one of two routes, and either route can get them there. Some pick them up by intuition. They watch how you react, and over time they get a feel for it. Others work them out on purpose, step by step. I'll come back to that in a minute.

Either way, each person on your team is working out answers you could write down once. All that guessing is what I mean by cognitive load. It's the thinking your people spend working out what you want, before they can even think about the risk. And your organization pays for every hour of it.

Okay, here's my story. I'm autistic, and I process explicitly, which means I'm one of the step-by-step people I just mentioned.

Early in my career, there were many times I'd see a risk and not know what to do with it. Do I raise this? Do I not? Does someone already know? And if they know, do they see the dependency I'm seeing, the other work this is going to touch? Or maybe they know, but they only see the isolated impact, just this one piece. And on and on like that.

Each of those questions takes real effort, and all of it happens before I've said a word to anyone.

What I learned came from the best leaders I had. They told me, don't worry about being sure. Raise the risk, and raise your thought process with it. Even if they already knew about it, they said, raise it. They told me it was about the risk, and it was also about helping me grow. And if they already knew, it gave us a chance to talk about how I was thinking.

Think about what that did for me. I could bring all those questions with me when I raised a risk, and they became what we talked about.

I kept that. When I grew into leadership roles, I made it my own neuroinclusive practice. By that I mean a way of leading that works for every kind of mind on the team. Raising a risk was about getting the work done. It was also about developing people, and making sure every way of thinking on the team got heard.

Someone on your team may be asking those same questions this week. Do I raise this? Does someone know already? With the skill I'm about to give you, you answer both of those in writing, before anyone has to guess.

So here's the skill. It's two lines and a name.

Start with one decision your team makes again and again. It might be whether a project's date still holds this week, whether a new hire is on track, or whether a customer is going to renew. For that one decision, you write two lines, once. You put them at the top of your team's risk list, or wherever your team tracks the work.

The first line says how much notice you need to change course. That's what early means, for that decision.

The second line says what you already know, and what would surprise you.

And under those two lines, you write one name. That's the one person who checks each new risk against your two lines. When a new risk would surprise you, or it leaves you less notice than you need, that person tells you the same day.

That's the whole skill. 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.

Let me give you three examples, from three kinds of teams, so you can hear how they sound.

The first one is a go-live. Say your team is moving your customer records to a new system, and the go-live date is set. The decision you keep making is whether that date still holds. Your first line reads, "I need four weeks' notice to move the date without paying a penalty." Your second line reads, "I already know the vendor's dates move, and two weeks of slip fits the plan. Anything that could put customer records at risk would surprise me." And under that, your project lead's name.

Now say the vendor slips a week. Your project lead looks at your second line. You already know vendor dates move, and a week fits the plan. So your project lead adds it to your team's risk list, where you'll see it.

The second example is a hire. Say you're hiring for a new role, and the work that person will do is already waiting. The decision you keep making is whether the hire is still on track. Your first line reads, "I need three weeks' notice to move the start date, so I can plan around the work that's waiting." Your second line reads, "I already know final interviews slip a week when calendars fill up, and that fits the plan. If two strong candidates turn us down for the same reason, that would surprise me." And under that, your recruiter's name.

So say two finalists in a row turn you down, and both give the same reason. Your recruiter checks your second line, sees that this would surprise you, and tells you that day.

The third example is a customer renewal. Say one of your largest customers comes up for renewal in the spring. The decision you keep making, month after month, is whether that renewal is on track.

Your first line reads, "I need six weeks' notice before the renewal date to bring in anyone who can help us keep this customer." Your second line reads, "I already know this customer pushes back on price every year, and that's normal for them. A new decision-maker on their side, or a complaint that's reached their leadership, would surprise me." And under that, your account lead's name.

So when the customer's long-time contact leaves and someone new will sign the renewal, your account lead knows what to do. Your second line says that would surprise you, so your account lead tells you that day.

So think of one of yours right now, a decision your team makes every week or every month. For your first line, ask yourself how many weeks you'd need to change course without it costing you. For your second line, ask what goes wrong on this kind of work so often that your plan already allows for it. That's what you already know. Then ask what would make you stop and rethink the whole plan. That's what would surprise you. Last, ask who on your team sees new risks on this first. That's the name you write under your two lines.

And you're like, okay, but my team makes a lot of decisions. Start with the ones that keep coming back, where a late warning really costs you.

Now think about how much care your organization already gives its systems. Think about the alerts it sets up on a budget tracker, or on an AI tool that flags unusual invoices. Somebody decides in advance what should trigger each one. And guess what the same organization gave the people on your team? One sentence. "Raise it early, no surprises."

Putting one name under the two lines comes from my Decision Charter, the framework I called DecisionOS until now. It's my framework for who does which job inside a decision. In it, reading the risks and making the call are two separate jobs. That's because the person with the clearest view of a risk is rarely the person who decides. So the person you name reads the risks, and you make the call.

So what stops happening once those two lines are written? Your people can look up what early means for each decision. Nobody has to say "I thought you knew," because your second line already says what you know. Your people get to spend their attention on the risk itself. And if a test run ever loses customer records, your project lead tells you that same day, while you can still move the date.

And when someone does bring you a risk you already knew about, you still thank them. And then you ask, what made you flag it? What did you see it connecting to? That's the kind of conversation my best leaders had with me, about how I was thinking.

The essay puts all of this on one card, the Operating Brief, in four parts.

The moment. A risk shows up late, or it shows up as news you already had.

The inherited design. Your team got one sentence, raise it early, no surprises. Then each person was left to work out, on their own, what early means to you.

The redesign. For each decision that keeps coming back, you write down once how much notice you need, what you already know, and what would surprise you. Then you name one person who checks every new risk against those two lines.

The Monday test. Pick one decision your team makes every week or every month. Write its two lines and that person's name at the top of your team's risk list. It needs nobody's permission.

The essay also prints a prompt. Take out people's and customers' names first, then paste it into the AI your organization has approved for its documents. It helps you draft your two lines and walks through each risk with you. The AI gathers what's known, and you judge which risks matter. That split comes from my AI Cognitive Strategy Matrix, my framework for which parts of the work go to AI and which stay with people.

The essay is on the site, under the title "Raise It Early" Needs Answers Your Team Can Look Up. The go-live's two lines are printed there, so you can copy them onto your own risk list and change them to fit your decision. The Operating Brief is there as a card you can take to your team. And the prompt is printed, so you can copy it rather than type it out.

Each week I work through one more piece of advice with you. Subscribe to the Substack, and bring each week's skill to your team.

And this week, take the decision you thought of a few minutes ago, write its two lines, and put one name under them.