In our first decade of Sterling Lawyers, I made tons of mistakes.
Four of them stand out, representing millions of real dollars that we lost or never earned.
I am certain of it.
Hopefully, you can stand on my wobbly shoulders and capture the revenue we lost!
Mistake #1: Not Joining a Legal Mastermind Group
One of my biggest early blunders was not surrounding myself with other lawyers.
While I joined a YPO (Young Presidents’ Organization) mastermind group filled with brilliant minds across industries, none were in law.
That was a blind spot I failed to recognize.
My arrogance, fueled by our rapid growth, convinced me I had all the answers. I didn’t look for a legal peer group because I didn’t think I needed one.
Looking back, that ego cost us years of insights and benchmarks that could have helped us avoid many mistakes.
There’s enormous power in connecting with people who face the same challenges in the same industry.
When we finally joined “Your Practice Mastered,” a legal mastermind run by Richard James, it transformed our firm.
Several excellent options are available today, like Pilma and Ben Glass’s program. Lee Rosen has an analogous program, too.
My strong advice to anyone starting or growing a firm: join a legal mastermind group as soon as possible.
It’s not just about networking—it’s about learning, benchmarking, and gaining insights you might be missing.
When you grow as a leader, your whole firm grows with you—a lesson I wish I had known from the start.
Mistake #2: Growth Hid Our Problems
The second mistake was getting caught up in our rapid growth, which blinded me to internal problems.
Doubling in size and revenue felt like a win every year. My ego soared. I felt really good.
That pace eventually exposed a serious issue – we lacked a system for handling cases. Each one was treated as a unique project, leading to inefficiencies that wasted time and frustrated both clients and our team.
Things improved once we introduced an Attorney-Paralegal workflow system.
Within weeks, our client service became more efficient, and the team worked better.
But our financial management was terrible. We were tracking nearly $10M in revenue through a basic Excel sheet..
One year, we overlooked real estate expenses in our forecast. By the time we noticed, we were already losing money while we thought we were profitable.
Growth can feel like progress, but it can also cover many flaws.
We’ve since developed better workflows and financial models.
I wish I had focused on building the right infrastructure earlier—it would have saved us many headaches.
Mistake #3: Lack of Focus on One or Two Priorities
My third regret is not keeping our goals laser-focused.
For years, I walked into planning sessions with five or six major priorities. The idea was that aiming high would help us achieve more.
The reality proved opposite—with a goal completion rate consistently below 50% each year, we were clearly spreading ourselves too thin.
In hindsight, concentrating on just one or two key priorities would have allowed us to channel all our energy into the most crucial tasks.
The book The One Thing captures this perfectly: identify the single task that makes everything else easier or unnecessary.
Had I adopted this mindset earlier, we would have been more efficient and seen stronger results.
I didn’t start learning this lesson until five or six years into our growth. Even then, limiting ourselves to three or four priorities was still too much.
Trying to accomplish too many things dilutes focus and reduces results.
If we had embraced the one-thing approach from the start, we could have avoided wasted effort and been further ahead as a firm.
Mistake #4: Not Supporting My Team Enough
Lastly, while I’m great at setting a vision and inspiring my team, I failed to provide the operational support they need.
My approach was pushing hard and setting ambitious goals. But I didn’t provide the structure or resources needed to achieve them.
This was unfair to the team and a near-fatal weakness in my leadership.
For years, I overloaded the team with work, expecting them to manage without proper tools or workflows.
Things improved once we introduced a proper workflow, but by then, we had been operating inefficiently for too long.
I also failed to consider that not everyone shared my independence. I assumed everyone would rise to the challenge as I did, which was naive thinking.
My team needed more guidance than I was giving.
Many teammates rose to the occasion despite my shortcomings. I’m so grateful to them for covering my weaknesses, but I wish I had recognized this flaw earlier.
Your team thrives when you support them as much as you challenge them.
Looking back, I realize that pushing without providing support isn’t sustainable.
I’ve worked hard to correct this. It’s still a work in progress.
I hope you can avoid my big four mistakes and shorten your own success curve!
