What I Learned After Hiring, Firing and Working With Lawyers for 30 Years
- 5 days ago
- 6 min read
Over the past thirty years I have worked with hundreds of lawyers.
Some have been exceptional.
Some have been average.
A few have been disastrous.
I have engaged lawyers for commercial disputes, business acquisitions, governance matters, intellectual property protection, franchising, employment issues, property transactions and strategic negotiations.
I have hired lawyers.
I have fired lawyers.
I have challenged invoices.
I have replaced entire legal teams.
I have sat on both sides of negotiations involving legal advisers.
I have worked alongside lawyers as a CEO, board member, business owner, consultant and advisor.
And after all those years, I have reached a conclusion that may surprise some people.
The lawyers who made the biggest difference were not necessarily the smartest lawyers.
They were not always the most expensive.
They were not always the most qualified.
And they were certainly not always the most aggressive.
The lawyers who delivered the greatest value were the ones who understood the objective.
They understood that clients do not buy legal services.
They buy outcomes.
That distinction sounds simple.
In reality, it explains why some legal engagements become enormously successful while others become frustrating, expensive and disappointing.
These are the lessons I have learned.
Lesson 1: The Right Lawyer Understands the Strategy
One of the most important lessons I have learned is that legal expertise and strategic understanding are not the same thing.
Many lawyers possess outstanding legal knowledge.
Far fewer understand the broader commercial strategy sitting behind the matter.
Years ago, I was involved in a significant commercial dispute.
The lawyer initially assigned to the matter was competent, intelligent and technically capable.
Yet we continually found ourselves at odds.
The problem was not legal knowledge.
The problem was that they did not understand the strategy.
More accurately, they did not appear interested in understanding the strategy.
As the matter progressed it became clear that I was spending more time explaining why certain actions mattered than discussing how to execute them.
Eventually I made the decision to replace the lawyer with a significantly more senior practitioner.
The hourly rate increased substantially.
On paper, it appeared to be a more expensive decision.
In reality, it became one of the cheapest decisions I made during the entire matter.
The senior lawyer listened.
They asked questions.
They sought to understand the commercial objective before recommending a legal pathway.
Most importantly, they recognised something that many advisers overlook.
The client understood the strategy better than the lawyer.
We ultimately achieved a hugely successful outcome.
The lesson stayed with me.
Legal expertise is essential.
Strategic alignment is invaluable.
A lawyer who understands both is worth their weight in gold.
Lesson 2: The Lawyer You Meet Is Not Always the Lawyer You Get
Many business owners assume they are engaging the person sitting across the table from them during the initial meeting.
Unfortunately, that is not always the case.
One of the more frustrating experiences of my career involved engaging a firm based largely on the credentials and expertise of senior practitioners.
Once the engagement commenced, much of the work was delegated elsewhere.
Again, delegation itself is not necessarily a problem.
Every profession develops future talent.
The problem arises when the person delivering the service lacks the experience, judgement or communication skills required for the matter.
Clients engage firms because they expect a certain level of expertise.
When there is a significant gap between expectation and delivery, frustration follows quickly.
This experience taught me to ask direct questions.
Who will actually perform the work?
Who will attend meetings?
Who will appear in court?
Who will draft the documents?
Who will review the strategy?
The answers matter.
A great legal engagement often starts with transparency.
Lesson 3: Not Every Hour Billed Creates Value
Most business owners understand that legal services cost money.
That is not usually the issue.
During one significant commercial matter, I discovered that a newly appointed legal department manager had become involved in discussions and meetings.
Their participation initially appeared reasonable.
However, as the matter progressed, it became apparent that much of their involvement related to becoming familiar with the file and developing their own understanding of the issues.
My response was straightforward.
I declined to pay for that time.
Not because the individual lacked potential.
Not because learning is unimportant.
But because I had engaged expertise, not education.
Clients should never be expected to fund internal training programs unknowingly.
The lesson is not that junior professionals should never be involved.
The lesson is that clients deserve transparency regarding who is working on their matter and why.
The best firms understand this instinctively.
Lesson 4: Aggression Is Not a Strategy
Many people assume that the toughest lawyer wins.
My experience suggests otherwise.
One negotiation in particular reinforced this lesson.
An opposing legal adviser encouraged their client to pursue an extraordinarily aggressive position.
The demands were ambitious.
The rhetoric was strong.
The legal arguments were extensive.
The ask was far too imbalanced.
Unfortunately, the strategy was detached from commercial reality.
Once the underlying assumptions became visible, much of the negotiating leverage evaporated.
The final outcome bore little resemblance to the opening position.
The client ultimately received a fraction of what had initially been demanded.
The lesson was simple.
Aggression and effectiveness are not the same thing.
The best negotiators understand leverage.
They understand psychology.
They understand timing.
Most importantly, they understand what constitutes a realistic and commercially achievable outcome.
Lesson 5: The Purpose of a Transaction Is to Complete the Transaction
I once observed a franchise sale where legal review appeared to become an objective in itself.
Every clause generated discussion.
Every discussion generated amendments.
Every amendment generated further review.
The transaction became trapped in an endless cycle of drafting and redrafting.
Eventually someone asked the most important question in the room:
"Are any of these issues genuinely material to the commercial outcome?"
The answer was largely no. The issues were however material to the opposing lawyer’s billing. He wasn’t happy when his client decided to move forward.
The transaction proceeded.
The buyer was happy.
The seller was happy.
The business performed well.
The world kept turning.
The experience reinforced an important lesson.
Perfection can become the enemy of progress.
Legal precision matters.
Commercial outcomes matter too.
The best lawyers understand the difference between a critical issue and a distraction.
Lesson 6: Lawyers Are Business Owners Too
One misconception held by many business owners is that lawyers automatically understand business because they advise businesses.
That assumption is not always correct.
Running a successful law firm requires exactly the same disciplines required to run most businesses.
Leadership.
Cash flow management.
Marketing.
Operations.
Recruitment.
Strategy.
Culture.
Financial discipline.
Some lawyers excel in all of these areas.
Others do not.
Over the years I have watched highly intelligent professionals struggle not because they lacked legal knowledge, but because they lacked business discipline.
The lesson is straightforward.
Technical expertise and business capability are different skills.
The strongest advisers typically possess both.
Lesson 7: Emotional Stability Matters More Than Most People Realise
Legal matters often arise during periods of stress.
Disputes.
Acquisitions.
Business failures.
Partnership breakdowns.
Employment issues.
Franchise disputes.
The emotions can be significant.
Lawyers are human, too. Their industry is ridden with conflict, stressful and compensated by often unhealthy outlets.
One of the most underrated qualities in any adviser is emotional stability.
The ability to remain calm.
To remain rational.
To remain objective.
To provide measured advice when others become emotional.
The best lawyers I have worked with brought perspective.
They reduced stress rather than adding to it.
They helped clients think clearly.
They did not inflame situations unnecessarily.
That quality is far more valuable than many people realise.
So What?
If thirty years of working with lawyers has taught me anything, it is this:
The best legal outcomes rarely come from the smartest lawyer in the room.
They come from the lawyer who understands the objective.
The lawyer who listens.
The lawyer who understands business.
The lawyer who understands strategy.
The lawyer who applies legal expertise in pursuit of a commercial outcome.
That is why finding the right lawyer is often much harder than finding a good lawyer.
And it is precisely why Bane Legal Services exists.
We are not a law firm.
We do not provide legal advice.
Instead, we help business owners identify legal professionals whose expertise, experience and commercial approach align with the challenges they face.
Because when the stakes involve your business, your assets, your reputation or your future, choosing the right lawyer should never be a gamble.
After thirty years of hiring, firing and working with lawyers, that may be the most important lesson of all.
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