Risk Versus Odds

As some readers may know, I retain a small commercial real estate practice. I apply as much of my thinking to my practice as workable. The upside is that my practice runs on very low overhead and is cost-effective for me and my clients. It also forces me to assess risk with my clients so that I don’t negotiate every sentence of every document; which is the essence of being a “trusted advisor.”

The downside is dealing with lawyers (most of whom are from Biglaw) for whom concepts of cost-effectiveness, efficiency and thoughtfulness are completely unknown; lawyers who can’t stop redrafting a 1,000 square foot lease because they see risk in every comma; lawyers who continually rephrase the wording (even their own!) because they feel it needs to be better “word-smithed” so as to avoid all risk for the client – while also, much more importantly, allowing them to CYA.

These unpleasant experiences remind me of the following words of my friend Geoff Wild in England:

It’s not surprising that most people typically think of lawyers as being cynics. Frankly, for whatever reason, mostly highly analytical individuals (which you need to be to get through law school etc.) tend to be cynical, likely because when you think about a problem for so long, it is easy to find flaws, risks and problems.

And when someone just focuses on problems for so long, they tend to end up, in the words of Tom Robbins, “sitting out the pan pipe hootchy-kootch of existence […] afraid to get their shoes muddy or their noses wet, afraid to eat what they crave, afraid to drink Mexican water, afraid to bet a long shot to win.” (Sounds like most lawyers, doesn’t it?) 

After a while, you start to recognize one of the key defining attributes of what separates a good lawyer from a bad lawyer is cynicism. 

Applying Wilde’s poetic structure, it’s kind of like this: 

A cynic is a person who knows the price of everything and the value of nothing. 

A bad lawyer is a person who knows the risk of everything, and the odds of nothing.

(Where the difference between ‘risk’ and ‘odds’ is the difference between what could happen and the likelihood of that thing happening).

Having someone tell you everything that could go wrong isn’t helpful for a business.

In fact, it’s outright harmful.

Business is all about taking risks.

The skill is in separating the good risks from the bad ones.

It’s about understanding outcomes and likelihoods, both good and bad.

That’s what good lawyers do.

They don’t just tell you what can go wrong. They also tell you what could (and should) go right, and how to maximize the likelihood of making that happen. 

Geoff is the award-winning leader at Kent County Legal, which managed to make several million pounds sterling in revenue for Kent County due to his superb management.

In other words, he knows what he’s talking about.


  1. I agree with these points and venture another one –
    A great lawyer is the one that goes even further and plans the steps you should take to mitigate the risk if the odds go against you and one of the unlikely risks actually happens. In short, a great lawyer includes advice on a Plan B.

    Incidentally, on the topic of cynicism, an old friend used to say ‘a cynic is just a disappointed romantic’. Maybe a ‘Hug a Lawyer Today’ campaign would help to soothe our souls and re-direct us away from agonizing over optimal comma placements…

  2. Isn’t the OBA already running a “Hug a Lawyer Today” Campaign…..?

  3. “After a while, you start to recognize one of the key defining attributes of what separates a good lawyer from a bad lawyer is cynicism.”

    Actually, Mitch, maybe that’s the case for transactional lawyers. That’s not for me to say. But it’s not the case for litigators. That’s because, except in the rare cases where a person comes to us before hand to ask about the risks of a problem – so he, she or it may decide if it’s a significant problem – nobody comes to us unless the person actually has problem, or has the perception of a problem.

    If you’re a transactional lawyer, you tell potential clients: here’s my card, I hope you’ll come to me.

    I tell people, certainly my friends: here’s my card, I hope you never need me (or someone like me) but, if you do … Of course, if it’s an institutional client, you know they’re going to need somebody like you at some point (even if they hope not) but, even there, in the real best of all worlds, they wouldn’t.

    See the difference?

    As to cynicism, well, there was once a law firm with two very able senior lawyers. The difference between the two? With one, you could see the knife coming.