How Business Owners Can Get More Value from Their Lawyers
Many entrepreneurs only reach out to their attorney once a problem has already taken root. But that reactive approach leads to higher legal bills, time lost, and avoidable stress. What if your lawyer could help prevent those issues in the first place?
This is a common frustration for business owners—bringing legal or tax-saving ideas to professionals who then confirm their value. The real question is: why aren’t they bringing those ideas to you first?
Why Lawyers (and CPAs) Don’t Usually Think Preventively
Legal and accounting professionals are trained to solve problems, not anticipate them. Their education emphasizes reacting to scenarios—analyzing what went wrong and figuring out how to fix it. That “problem-solving mindset” doesn’t naturally include looking ahead to spot potential issues.
Most lawyers and CPAs also don’t run businesses themselves. That creates a knowledge gap between what you’re experiencing day-to-day and what your advisor understands about your company’s activities, goals, or risks.
The “Technician” Problem
Many professionals are excellent technicians—they can handle the task you give them. But they aren’t always trained or expected to step back and look at the bigger picture of your business. If you don’t bring an issue to them, they won’t know it exists. That leads to missed opportunities and preventable problems.
Why Regular Check-ins Don’t Always Work
One proposed solution is scheduling consistent check-ins with your attorney. But this can create new problems:
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If you don’t need legal help at the time, the meeting wastes your time.
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If your attorney bills hourly, you’re paying for meetings without a clear purpose.
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If they don’t bill for that time, their business suffers—and the relationship may not last.
A Better Approach Legal-Savvy Business Owners Use
The business owners who avoid legal messes tend to take a different route. Instead of relying on their lawyer to initiate guidance, they learn to spot legal issues themselves—before those issues grow into problems.
This doesn’t require a law degree. It just takes a framework.
The Legal Operating System for Business Owners
The Legal Operating System was built for exactly this. It’s a toolset that helps business owners learn to identify potential legal risks early, when they’re easiest and cheapest to deal with.
What It Includes
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A legal checklist: This outlines the common problem areas business owners run into, from contracts and tax planning to intellectual property and hiring practices.
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Routine check-ins (on your own terms): Instead of calendar-based meetings with your attorney, you work through the checklist at regular intervals that fit your business.
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Free training: This teaches you or a key team member—like a COO or office manager—how to think through legal issues the way an attorney would. It focuses on real-world business challenges, not law school theory.
Spot Legal Issues Early, Save Time and Money
With a bit of upfront effort, you’ll get much more value from your attorney. When you contact them, it’s not to fix a fire—it’s to build a better foundation.
And the savings are significant. Many legal problems can be avoided entirely with early planning. The estimate? About 90% of legal costs can be cut just by acting before trouble hits.
Think of what that means:
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Fewer distractions
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Fewer legal fees
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More confidence in your contracts, tax elections, and intellectual property protections
Build a Stronger, More Protected Business
No one knows your company better than you. But your attorney can still be a key player—if they have the information and context to help. By using the checklist and training resources, you’re not replacing your attorney—you’re equipping them to do their job better.
Your business becomes safer, more profitable, and easier to run. And your team can stay focused on growth instead of firefighting.
Ready to get started? The checklist and training are available at no cost. Use them to make better legal decisions before problems arise.
Video Transcript
Frustration with Reactive Advice from Professionals
Have you ever wished your accountant or attorney would help avoid problems rather than just being there when you have problems and saying, “Oh yeah, we could do this to avoid it.” I was really frustrated few years ago, well, maybe a decade or more ago. When I would contact my CPA. And I would ask, uh, questions about something that I might have heard on YouTube or might have read about, and he’d say, oh yeah, you can do that.
That will save you some money. And I thought to myself, “why am I bringing that to you? Why don’t you bring that to me?” I am going to explain a couple of reasons why that happens and then how you can avoid that both with your lawyer and with your CPA.
How Legal and Accounting Professionals Are Trained
So here is why it happens. First off, when we go to school as lawyers and CPAs are probably similar, you are focused on a lot of solving problems. You are presented a fact pattern. You need to identify the issues, the problems, if you will, and then you work on how to solve them. And so that gets trained in us from very early age. Problem is presented, we solve it, and then we take care of the client. What you’ll notice there though, is it’s not preventative.
Legal Scenarios Not Viewed Through a Prevention Lens
It’s not saying, “Hey, here’s a scenario. What can we do to prevent potential problems?” For example, let’s say a client has a business with employees and some products and some services, a website, um, and, uh, a a rented location. What are all the legal issues that could go bad? What are the legal problems that could come up there and how do we prevent them?
CPA Training Focuses on Response, Not Strategy
So lawyers aren’t trained that way. Likewise, CPAs go through training where they are given all sorts of scenarios. They are asked questions, but they are not necessarily stepping back and saying, “Hey, how do I save money for this client? How do I come along as a real trusted partner who knows the company and can prevent that?”
The Technician Problem
So that is one problem. Sometimes I call it “The Technician Problem” In other words, lawyers and accountants are great technicians. They are not trained as business owners to think about the future and prevent that, uh, especially since most of them don’t have experience running a business. So that is the technician problem.
Professionals React Rather Than Anticipate
They solve problems. They are not preventing them.
The Disconnect Between Attorneys and Your Business
The next problem is this. Attorneys and CPAs don’t know your company. They don’t know the products and services you are launching. They don’t know the new contracts or relationships you are entering into. Now, sure. If you come to the attorney and say, “I need a contract, um, we are working on setting up a relationship with this new supplier. Can you take a look at this or can you draft a contract for us?” Sure. The attorney knows then. But what about when you or your team is out there setting up new relationships? As an attorney, we don’t know that.
Regular Check-Ins Don’t Always Make Sense
And so at first when I was practicing, I thought, “Well, the solution must be to have regular check-ins with the attorney so that you can share what is happening in your business.”
But sometimes those check-ins were not needed and uh, sometimes a check-in involved a lot of different issues. And so as I talked with my clients who had become friends, I said, “How often should we be checking in? What does that look like?” And they said, “You know, it doesn’t really make sense to have a regular check-in. My time is valuable. And Aaron, your time is valuable.” They said, either “Aaron, you are not charging for that time and so you are getting behind financially or you are charging for that time, and that means I am paying for meetings that I don’t need,” so that didn’t work very well.
What Actually Helped
You might be wondering, well, what did work? How did we end up solving this? Well, we haven’t perfectly solved it, but there is a technique or an approach that is used by many great business owners that does solve this. And here is the issue. The business owner takes a little time to learn how to identify legal issues related to their business so that when the issue comes up, they spot it before it is a problem, and then they reach out to the attorney and they share that and say, “Hey, how do we get on top of this? How do we prevent this from turning into something bigger?” So that is the approach.
How the Legal Operating System Works
I implemented with the Legal Operating System. The Legal Operating system is a system I put in place to help clients and then also to just give away to the public so business owners can help avoid problems in their company.
Here is how it works. First, it is a checklist of legal issues that you can use to spot potential problems or legal needs before they become a problem or an expense or a distraction. So it is a checklist that you go through from time to time.
Setting a Routine Review
And then second, you set a routine where you will come back and make sure you are staying on top of this.
Training for Spotting Legal Issues
Third, there is training available. Now, I think the training is best for the founder or the visionary, but often the founders say, “Hey, I don’t have time. I don’t really wanna sit there for three hours of training. I will delegate that to my staff.” And often that works as long as a COO or a chief of operations or office manager is thinking through that list and takes the time to understand how do you spot legal issues like a lawyer would. These issues are not everything they train in law school. That would take three years. What they are are the issues that I have seen time and time again that are presented by my new clients, and I realize, “Hey, this could be prevented.”
What You Can Do Now
So what can you do about this? Take the time to get the checklist to identify these issues in advance, and then either delegate to your team or take the time yourself to educate yourself on how do I spot these issues. The checklist helps, but instead of just having a checklist, which might require some knowledge of the law, I have free training. And with that training, you will now better understand all of the I items on the checklist so you can preventatively spot those issues and then ask your attorney about them.
The Impact of Preventative Legal Planning
In my experience, clients can reduce their legal fees by about 90%. That means 10% of the problems you can’t eliminate altogether, but 90% you can with some preventative planning and getting your attorney involved ahead of time rather than cleaning up a mess later.
Why Planning Costs Less Than Problems
Litigation and legal disputes and audits, those are far more expensive than the time spent ahead of time working with your attorney to have a solid contract, protect your intellectual property, make sure your tax planning and elections are in order.
Final Encouragement to Business Owners
So please go check out that checklist and the training. It is all free. We are not withholding it from anyone because my hope is that you and your attorney can work together to make a better company. A better company for you. It is more profitable. It also is less legal fees, less legal problems that distract your team so your team can focus on what is most important, your company’s vision and your company’s goals.