Corporate Lawyer’s Top 10 List of Successful Outside Counsel Habits: #6 Being Creative and a Freethinker so You Can Find Your Dunkirk

6.? You are creative.? You fight this war and not the last war.

We have all heard Winston Churchill’s speeches.? We know how he was a great communicator and how it helped inspire the Allies to WWII victory.? But I think his greatest quality was how he constantly challenged the status quo thinking with his war staff, including very senior-level Generals.? There is a lesson there for leaders.

If you have not read Churchill and Orwell: The Fight for Freedom, I highly recommend it.? It describes how Churchill ran his meetings as a “continuous audit of the military’s judgment.”? He would take an inquisitive approach and say, “it is always right to probe.”? While he might not have been popular for this approach with his staff, eschewing consensus building, it would reveal assumptions that his staff made WITHOUT EVEN REALIZING THEY MADE THEM.? The author goes on to say about his meetings:

If meetings are not contentious, they probably are not productive – especially planning sessions.? This is often unpleasant, especially for the advisors, but it is the best way to develop strategy and to uncover one’s weaknesses before the enemy does.

It is this challenge and re-challenge approach that led to discovery of the idea for Dunkirk.? A large portion of the British Army was trapped and pinned down by German forces in Dunkirk, France. ?Civilian boats were sent to rescue huge numbers of troops so that Britain and the Allies could live to fight another day.? It was an out of the box idea and it worked.

Despite the complexity of our legal and compliance matters, I am struck at how frequently advice and counsel can resort to the same plays out of the same playbook.? While I acknowledge that some strategies are tried and tested, we are not doing our jobs if we do not question whether to resort to those tactics again.? Without this constant check, we become predictable and make it easier for our adversaries to plan their strategy.? “That is the way it is always done” is the most dangerous kind of thinking that we can do.

How can you stand out to clients in this regard?? Here are a few ideas:

1. Never apologize for being the lone voice.? The best way to distinguish yourself is to come up with unique ideas that do not fit the mold or “group think.”
2. Just because an approach worked for your last case or legal matter does not mean it will work here.? Show your client you challenged your thinking to determine if the same strategy was really warranted and, if it is not, then pivot.
3. ?On critical decisions, create a Red Team.? The Red Team will plan and develop a strategy as if they were your adversary.? It will show that you have tried to flip perspectives in developing a client’s strategy.
4. Don’t regret or linger on the awkwardness of healthy conflict.? It is uncomfortable, yes, but it will be gone tomorrow.? What will remain are the great ideas that are sparked and better results for our clients and companies.
5. If there is a consensus, ask this simple question as a leader if the debate has not been robust enough: “Has anyone not expressed an opposing view to this strategy before we move forward?? I want to be sure we get this right and need to know if anyone has any objections, concerns, or better ideas.? Nothing is straightforward here. Please share them if you have a different idea.”

I believe the next great idea is always out there and only a small boost in courage away.

-Brennan