I promised a few posts back that I’d only cash the cockpit analogy once a quarter. It’s been a quarter. This one earns it.

Before an airline crew pushes back from the gate, we run what’s called a threat-and-error briefing. It is not the checklist — the checklist comes later and confirms that we did the things. The briefing comes first, and it does something different: it forces the crew to say out loud, to each other, what is unusual about this flight, on this day, and what could bite us. Construction on the field that complicates the taxi route. A short runway with a tailwind. Mountainous terrain on the departure. Convective weather sitting over the arrival airport that isn’t there yet but will be by the time we get there. We name the threats before we’re moving, because the worst time to first consider a threat is the moment it becomes a problem.

The whole premise of that briefing is a humbling one: we already know we don’t know everything about how the next three hours will unfold. The briefing is how we mitigate risk inside that ignorance instead of pretending it away. Which brings me to a passenger I used to fly.

A Word About Rumsfeld

In my corporate flying years, before the airline, I flew Donald Rumsfeld. For readers who don’t carry the 2000s around in their heads: Rumsfeld was U.S. Secretary of Defense twice — the youngest ever under Gerald Ford in the 1970s, and again under George W. Bush from 2001 to 2006. He’d been a Navy aviator, a congressman, a White House chief of staff, and a corporate CEO before that. He died in 2021. Sharp, precise, and — this matters for what follows — a man who thought carefully about the structure of what he did and didn’t know.

At a Defense Department briefing in February 2002, Rumsfeld gave an answer that got mocked at the time and has aged into something close to wisdom:

“There are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know.”

Say what you want about the man’s politics. As a framework for managing risk, that is nearly perfect, and every good pilot and every good examiner already lives inside it whether they’ve named it or not.

The Three Categories, in a Cockpit and on a File

The known knowns are the easy part. On a flight, that’s the fuel load, the aircraft weight, the published approach. On a title file, it’s the legal description, the vesting deed, the open mortgage of record. You look, it’s there, you clear it. Nobody generates a claim out of a known known.

The known unknowns are where the work actually is. In the cockpit, I know I don’t yet know exactly what the weather will be doing at the destination, so I carry extra fuel and brief an alternate. On a file, the examiner knows there are things the record hasn’t told them yet: whether that “release” was ever actually recorded, whether the estate in that 2009 probate was fully administered, whether the survey will match the legal, whether the party who signed as “attorney-in-fact” actually held a valid power at the time. These are the risks you can name in advance. The entire craft of examination is converting known unknowns into known knowns before closing — and, where you can’t, insuring or excepting around them deliberately rather than accidentally.

The unknown unknowns are the ones that keep underwriters up at night. The forged release you had no reason to suspect. The heir nobody knew existed. The fraud that was designed specifically so it wouldn’t show up in your search. You cannot brief a threat you can’t imagine. But — and this is the part aviation figured out the hard way, over decades of accident investigations — you can build a system whose margins absorb the threats you didn’t see coming. Extra fuel doesn’t just cover the weather you forecasted; it covers the divert you didn’t. That’s the point of margin.

What a Threat-Forward Briefing Looks Like on a Title File

Try this on your next commitment, before the examiner opens the file in earnest. Two minutes, out loud or on paper, answering one question: what is unusual about this file, and what could bite us?

Cash deal closing in four days with an out-of-state seller and a power of attorney? That’s your construction-on-the-taxiway — a compressed timeline stacked on top of an execution risk. Name it now. A recent transfer for nominal consideration between LLCs with overlapping members? That’s weather building on the arrival; it may clear, but you’re watching it. A property that’s been in the same family since a 1970s deed with a gap where a release should be? Mountainous terrain — you know the risk is structural, so you route around it deliberately. Rural parcel, metes-and-bounds description, no recent survey? You’re flying into an airport you don’t have good plates for; slow down.

None of these are exotic. That’s exactly the point. The threats that generate claims are almost never exotic — they’re ordinary risks that nobody said out loud because everybody assumed somebody else had looked. The briefing is the forcing function that makes the file’s specific hazards explicit before the clock is running, not after.

Where the Software Earns Its Keep

A briefing is only as good as the information in front of the crew when we give it. This is the part I actually built a company around. Scribe reads the file and surfaces the threats for you — the gap in the chain, the release that doesn’t reconcile, the vesting that doesn’t match the seller on the contract — so the examiner walks into the briefing already knowing where the terrain is, instead of discovering it three exceptions deep at 4:45 on a Friday. It doesn’t make the judgment call. It makes sure the known unknowns are on the table where a human can see them.

And Sentinel Plus covers the category you can’t brief. Payoff and wire fraud is the modern unknown unknown of a closing — engineered specifically to look normal right up until the money is gone. You can’t name that threat file by file, so you build a system that verifies systematically regardless of how ordinary the transaction looks. That’s not paranoia. That’s margin, the same way the extra fuel is margin.

Aviation didn’t get safe by getting lucky with the weather. It got safe by admitting, before every single flight, that it didn’t know everything — and then building the briefing, the margins, and the tools to fly well anyway. The title industry already has examiners with that instinct. The job is to make the instinct a system.

That’s the briefing. Threats identified, margins set, cleared for the approach.

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