Lawyers and Leaders, Winning Too Much Can Cause You to Lose

Team of Lawyers Celebrating Winning Strategy
What is the #1 problem that most executives that my mentor Marshall Goldsmith, the #1 executive coach in the world, has coached suffer from? You might be surprised and on the surface, the answer to this question may seem counterintuitive, but if you’ll stick with me for a moment I’ll share the answer with you along with why the answer is so important for you as a lawyer or law firm leader.
As lawyers, there is certainly no shortage of pressure on you to win. Your clients want you to win cases and negotiate winning deals. Your partners and your families want you to win new business. Sometimes, if you’re honest with yourself, your ego and your strong drive to succeed may push you to want to win at everything you do.
Plus, if you’ve worked your way up to a leadership position within a law firm, there’s a real good chance you’re good at winning and … winning a lot.
But, can winning become a problem when you win too much?
Marshall Goldsmith had the privilege of spending 50 days with the world’s greatest authority on management — Peter Drucker. During his time with Peter, Marshall learned a very important lesson.
Coaches spend so much time helping leaders learn what to do, that they forget to help leaders learn what to stop doing. In reality, a majority of the leaders Peter met already knew what they needed to do. So, instead of being coached on what they needed to do, what was far more valuable was learning what not to do and when they should stop.
That comment led Marshall to write his book “What Got You Here Won’t Get You There.” That book became a best-selling book in 12 countries and was translated into 30 languages. All thanks to what Peter Drucker shared with Marshall.
So, going back to the question above, “What is the #1 problem of most executives that Marshall Goldsmith has coached?”
— the answer is… winning too much.

What does “winning too much” mean?
It’s simple: a lawyer, leader, or CEO who gets too caught up in winning might become a long-term loser.
Winners love winning. Indeed, it’s incredibly difficult for highly successful lawyers and leaders not to or try their best to win. To help you understand the impact of winning too much in your daily life, here’s a short case study.
Imagine that you have just returned home after a long hard day at work. You open the door and your significant other says, “I had such a hard day today.” Many lawyers and leaders will respond with, “You had a hard day? You? You have no idea what I had to put up with today!”
Lawyers and leaders tend to be so competitive that they have the urge to constantly prove that they are more miserable, stressed out, or tired than the people in their lives. Marshall gave this example at a class at Dartmouth’s Tucks School. One man raised his hand and said that he got himself caught up in that trap last week with his wife.
Seeing the man’s reaction, his wife looked at him and said, “Honey, your hard day is NOT over, in fact, it just got harder.”
So, the next time you start trying to win, take a deep breath and ask yourself — what exactly are you winning here?
6 Key Takeaways in Winning vs Leading
Winning is not everything
Great lawyers, CEOs, and entrepreneurs tend to be naturally competitive. Each of you often focuses on the goals you want to achieve, builds an action plan to hit those goals, executes the plan, and then keeps track of your progress and wins for both yourself and your company.
Being hyper-competitive can also unconsciously lead to creating a habit of trying to “win” in everything, however, including winning even small arguments with no real value. This habit can make you feel like it’s your job to prove how smart and right you are, every time. So, if you catch yourself turning every trivial issue into a battle to prove something — it’s time to reassess your priorities.
Accept that you’re not always the boss
The most successful lawyers and law firm leaders often have a hard time admitting that they don’t always have all the power. You might have a board of directors to answer to, a business partner who has to sign off on a big decision, or a life partner who has a say on what you’ll be having for dinner.
One of Marshall’s mentors once told him, “Every decision in the world is made by the person who has the power to make that decision. Make peace with that.” Even if you don’t have a final say in a decision, you still have the power to influence the decision-maker in a positive way.
Focus on the big picture
One way to avoid getting caught up in trivial battles is to avoid trivial tasks — because engaging in tribal tasks should not be your responsibility. As the leader of a law firm, your main responsibility is to create a big vision and set big targets for the firm’s future. Once you’ve done that, your next responsibility is delegating tasks to people so you can achieve your goals.
You are not supposed to be a micromanager who is constantly going around picking fights to remind your employees who is in charge. Before you start on any task, ask yourself “How is this task going to help me accomplish my big goals?” If it’s not, then delegate it to someone else, and focus on the big picture that will grow your company.
Let others claim the credit
When someone comes to you with an idea, what do you usually do? Law firm executives and other leaders often have the tendency to add on to an idea instead of simply giving all the credit to the employee who first thought of the idea. Some might do this solely for the sake of the welfare of the company, but others might do it just to show that they are smart and can contribute ideas too.
The problem with this is, the quality of the idea may only go up by 5%, but the employee’s motivation to execute the idea might go down drastically. Why? Because they no longer feel like it’s their idea. So, sometimes, it’s best to step back and let others take all the credit.
Use feedback to your advantage (and feedforward)
If you’re too focused on winning every argument and want to be seen as the smartest person in the room, you will create a work environment in which your employees will keep their opinions and ideas to themselves. They will be too afraid of expressing their opinions, afraid of being wrong, of being judged or of trying new things. This will quickly grow to become a toxic culture for your company — which will stifle creativity and growth.
As a law firm leader, you have to be open to suggestions, not only for the sake of getting fresh ideas, but also to build a sense of ownership in your team. By being open and providing a psychologically safe environment, your employees will follow your lead and support each other too. This is crucial in building a positive and high-performing team.
Adapt your leadership style accordingly
When you open yourself up to feedback from your employees, you can gain insight into what kind of leadership style is suitable for your team. A new lawyer or junior partner might need firm hand-holding while they are getting situated in your company or a new role with new responsibilities. A C-suite colleague might prefer it if you adopt more of a coach-like behavior instead of a supervisor. Employees who know exactly what they need to do might just need you to leave them to do their job perfectly. This is what we refer to as Full Spectrum Human Leadership.
What exactly are you winning?
If you look at law firm advertisements and websites, you’ll see that many of them make promises about things like “providing aggressive representation” or “fiercely representing our clients.” After all, the very backbone of our legal system is adversarial in nature, right? But, is being fierce and aggressive always the right way to be?
Marshall recently received an email from a student in his class thanking him for his story about trying to win at everything. The email read as follows:
“Yesterday my wife called and was talking about what a tough day she had. I was just getting ready to point out how her problems paled in significance to my own, but for some reason, I remembered what you said five years ago. I stopped, I breathed, I listened to my wife and I said, I love you, thank you for all the sacrifices that you’ve made for our family. I bought some flowers, went home, I said I love you to my wife and gave her the flowers. That was the best $25 I ever spent, thank you very much.”
So, if you start trying to win something trivial just for the sake of proving how right or how smart you are, take a deep breath and ask yourself “What exactly am I winning here?” Is this really something I want to win or need to win? Is it even worth the effort? Does winning move this relationship forward or backward?
When you stop and think about it, there are lots of opportunities for lawyers and leaders to become more successful if we appreciate this “flaw” of winning too much and work to suppress it in all of our interpersonal relations.