Biglaw, In-House Counsel

Inside Straight: The Unfairness Of ‘Are You Sure?’

In Proof of an External World, G. E. Moore famously defended the concept of certainty: Moore could put his hand in front of his face and say (with certainty): “Here is a hand.”

Ludwig Wittgenstein disagreed. Wittgenstein was uncertain whether he knew — with certainty — that the hand in front of his face actually existed. The first sentence of Wittgenstein’s On Certainty reads: “If you do know that here is one hand, we’ll grant you all the rest.”

(Hah! You thought you came to Above the Law to read about bonuses and pictures of naked judges. It turns out that we’re epistemology through and through. But I digress.)

On three recent occasions, I’ve heard (or heard of) people asking, “Are you sure?”

I’m with Wittgenstein on this one: I can’t even tell you that “this is my hand,” for heaven’s sake; how dare you ask if I’m sure about a legal judgment?

The first “Are you sure?” did not arise in a legal context. A guy got off a subway, emerged from under ground, pulled out a map, and told the woman he was with: “We should walk this way.”

She asked, “Are you sure?”

Now look: The guy had a map in his hand; he had just emerged from under ground; and he was considering the situation. I have a creeping suspicion that he wasn’t sure; he was probably giving his best assessment of the situation.

Given that, I don’t think his companion was actually asking whether he was sure; she knew that he was uncertain. Rather, his companion was setting the guy up for a fall: Fifteen minutes from now, when this couple was lost in a bad part of town, she could blame him for having put them in this situation — because “I told you that this was the wrong way!”

Actually, she did no such thing. She didn’t affirmatively say: “No, north is wrong. I believe that we should walk south.” In fact, if her companion had proposed walking south, she still would have said, “Are you sure?” This had nothing to do with conflicting opinions; this was just positioning herself to complain.

Move into a legal context: One in-house lawyer says that we should take this action, or assume this risk, or try this case, or set this reserve. And another in-house lawyer says, “Are you sure?”

The first lawyer may not have been holding a map in his hands, but I guarantee you that he wasn’t sure. He was giving his best informed legal judgment and proposing a course of action. There’s no certainty in that world; you’re just doing the best you can do. If the second lawyer preferred to put his neck on the line, then the second lawyer should have said: “I disagree with you. We should not follow the course of action that you propose, but instead follow this other course of action that I propose.”

But that would put the second lawyer at risk: You could follow his advice, and he could be proven wrong. The second lawyer didn’t want to take that chance, so the second lawyer didn’t actually offer advice. Instead, he simply asked, “Are you sure?” Then, when things don’t work out well, the second lawyer can complain: “I told you that this was the wrong decision!”

Last example: Outside counsel recommends a course of action to a roomful of clients. In-house lawyer then asks, “Are you sure?”

That’s the same mock uncertainty all over again. This is legal advice; it’s not holding your hand in front of your face and struggling to deduce whether your hand exists. If you disagree with the advice, say so, and let us know what you think. But don’t just set your outside counsel up as the fall guy: “I told everyone he was wrong!”

If you need certainty about outside counsel’s advice, then hire a second outside law firm, shell out another $20K, and get a second opinion. And then hire a third law firm, and get a third opinion. And a fourth. And a fifth. And resurrect G. E. Moore and Ludwig Wittgenstein. Maybe you’ll find yourself some certainty.

But let’s not innocently ask, “Are you sure?”

If the legal question was a hard one, then the answer is uncertain.

That’s a proposition I know for sure.

Once I figure out whether this thing in front of my face is my hand, I’ll let you know about the rest.

Mark Herrmann is the Chief Counsel – Litigation and Global Chief Compliance Officer at Aon, the world’s leading provider of risk management services, insurance and reinsurance brokerage, and human capital and management consulting. He is the author of The Curmudgeon’s Guide to Practicing Law (affiliate link) and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide. You can reach him by email at

(hidden for your protection)

comments sponsored by

Show all comments