About the Firm · Stephen H. Lebovitz

What I Have Learned Practicing Law in Pittsburgh: Notes From a Third Generation Attorney

---

Most people call a lawyer after they have already made the decision that hurt them. They signed the contract. They distributed the estate assets. They agreed to the settlement. They accepted the offer. Then something went wrong and now they want to know if anything can be done.

Sometimes something can. Often the options are much narrower than they would have been before. The call that comes before the decision, before the document is signed, before the asset is moved, before the agreement is made, almost always costs less and produces better results than the call that comes after. This is true in every area of law I practice. It is one of the few things that is true in all of them.

I have seen estates worth $50,000 produce litigation that cost more than the estate. I have seen estates worth several million dollars close without a dispute. The difference is rarely the size of the estate. It is whether the family talked about it before someone died.

When a parent tells their children what they intend to do with their estate and why, the children may not agree but they understand. When a parent dies without that conversation and children open a will that surprises them, they often fight, not because they need the money but because they feel something was hidden. The estate plan is not just a legal document. It is the last communication about what mattered to the person who wrote it. When that communication happens while the person is alive, it lands differently.

This is not a criticism of anyone who contested a divorce. Sometimes the fight is necessary. Sometimes the principle matters more than the cost. But in my experience, the couples who recognize early that a dollar spent on litigation is a dollar neither of them keeps, and adjust their expectations accordingly, almost always end up in a better position than the ones who do not.

The cases that resolve in months instead of years are not always the ones where the parties agreed on everything. They are often the ones where both sides had lawyers who could explain the math clearly and clients who were willing to hear it.

I have reviewed agreements of sale, business contracts, partnership agreements, and operating agreements for decades. The problems I find are almost never exotic. They are missing terms, ambiguous language, and obligations that are defined differently by each party. The document looks fine until something goes wrong and it turns out the parties meant different things by the same sentence.

The most expensive contracts I have ever seen litigated were the ones nobody reviewed before signing because they seemed straightforward. Real estate contracts. Business purchase agreements. Partnership arrangements between friends. The relationship made the legal formality seem unnecessary. Then the relationship changed and the contract had to carry weight it was not built to carry.

Pennsylvania executors are entitled to reasonable compensation. Most executors who are also beneficiaries of the estate do not take it, and that is usually the right call. The fee is taxable income. Taking it reduces your share of the estate. And in my experience, the executor who takes a fee in a family estate almost always hears about it from the other beneficiaries, even when the fee is entirely reasonable and legally appropriate.

The exception is the executor who is doing significant work — managing real estate, running a business, dealing with litigation — where the time and exposure justify compensation. In those cases the fee is earned and not taking it is a different kind of mistake. The question is whether the work actually warrants it, not whether you are legally entitled to it.

I receive calls regularly from beneficiaries who believe the executor is stealing from the estate. In most of those cases, the executor is not stealing. They are slow, uncommunicative, disorganized, or simply unaware of their obligations. The money is there. The estate is being administered. It is taking longer than the beneficiary expected and no one is explaining why.

But the instinct that something is wrong is sometimes correct. The cases where the executor actually was misappropriating assets — and I have handled those — often started with exactly the same call. The difference between a slow executor and a dishonest one is not always visible from the outside. That is why the call is worth taking seriously even when the answer turns out to be ordinary.

This is one of the most consistent things I have observed across over thirty-five years of personal injury practice. The first offer reflects what the insurer believes you will accept, not what the claim is worth. They make early offers because early settlements close files before the full extent of injuries is known, before liability is fully investigated, and before the claimant has representation.

I am not suggesting that every claim is worth more than the first offer. Some are not. But the offer made in the first weeks after an accident is almost never made with complete information about the injuries, the treatment course, or the long-term consequences. Accepting it closes the file permanently. What develops after that is the claimant’s problem, not the insurer’s.

This sounds self-serving. I am aware of that. But it is also consistently true. The clients who do best are not necessarily the ones with the strongest cases. They are the ones who tell their lawyers everything, follow advice they do not always agree with, and resist the urge to act unilaterally when the process is frustrating them.

Litigation and negotiation have their own logic and timing. A client who sends an angry email to opposing counsel, posts about their case on social media, or confronts the other party directly often makes their own case harder. The ones who stay disciplined — especially when it is difficult — almost always do better than the ones who do not.

Allegheny County has a small bar relative to its population. The attorneys who practice here regularly see the same judges, opposing counsel, mediators, and expert witnesses in case after case. Reputation matters in ways that are hard to quantify but easy to observe. An attorney who is known for being reasonable, prepared, and honest in dealing with other lawyers gets different treatment than one who is not.

This is not unique to Pittsburgh. But it is more pronounced in a market this size. My grandfather built a reputation over decades that my father inherited and I have continued. The relationships that span generations in a local bar are not just pleasant — they are professionally useful in ways that matter to clients.

Law is a tool. Like any tool, it is most useful when applied to the right problem and least useful when applied to the wrong one. I have seen neighbors litigate over a property line dispute that a surveyor could have resolved for a fraction of the legal fees. I have seen families fight over an estate through lawyers when a conversation over dinner might have accomplished more.

Part of what I try to do in the first consultation is understand whether the legal system is actually the right place for this problem. Sometimes it is the only option. Sometimes the client has already tried everything else and litigation is what remains. But sometimes the better advice is to talk directly, hire a mediator, or accept a less-than-perfect outcome and move on. I have given that advice when it was warranted. It is not always what the client wants to hear. It is sometimes the most valuable thing I can tell them.

If I told a client on the first day exactly what their divorce would look like at the end — the custody schedule, the asset division, the support amount — most of them would not believe me. Not because the prediction would be wrong. Because they are not ready to accept it yet. They are still in the early stage, when the loss is fresh and the position feels non-negotiable and the principle feels worth fighting for at any cost.

This is true in most contested matters, not just divorce. The client who has been wronged, or believes they have been wronged, needs time to move through what happened before they can see clearly what is possible. Part of the job is understanding where someone is in that process and not pushing them toward a resolution they cannot yet accept. The ones who get there eventually almost always land in roughly the same place the experienced lawyer saw on day one. The difference is how much it cost to get there.

I have seen clients spend $40,000 in legal fees to win a $15,000 dispute because the other side was wrong and someone needed to say so. The principle was real. The victory was real. The net result was a significant loss.

There are times when principle is worth the cost. When the wrong is serious enough, when the precedent matters, when walking away would cause more damage than fighting. I have taken those cases and I do not regret them. But the decision to fight on principle should be made with clear eyes about what it actually costs — financially, emotionally, and in time. The person who wins on principle and loses everything else has not always made the right choice. The person who compromises a position they were right about and moves forward with their life sometimes has.

I have seen clients with $15,000 in liability coverage face a $200,000 claim. I have seen homeowners without an umbrella policy lose everything they built because of one accident on their property. Insurance is the one legal protection most people already have access to and most people underuse.

Some clients are sophisticated enough to self-insure certain risks. That works until it does not. The question is whether you have actually modeled the downside or whether you have decided not to think about it. The clients who have thought through their coverage honestly almost always have fewer catastrophic surprises than the ones who have not.

The best transactions are the ones where both sides want to close. When I know something can be done — that the title is insurable, that the structure works, that the risk is manageable — I can help get everyone to yes faster. Experience is what makes that possible. A lawyer who has closed hundreds of transactions knows which concerns are real and which are reflexive. That knowledge shortens the path.

The lawyers who slow deals down are often the ones who have not done enough of them to know what is actually possible. Caution is warranted. Paralysis is not. There is a difference between identifying a real problem and inventing one.

My father used to say this. I have found it to be consistently true across every area of law I practice. Financial statements in divorce cases, estate accountings, business valuations, and damage calculations can be technically accurate and deeply misleading at the same time. The numbers are right. The story they tell is not.

Knowing the difference requires understanding what the numbers are supposed to show and what has been left out. It requires asking the question behind the question. This is not about assuming dishonesty. It is about understanding that selective presentation of accurate information is its own form of misleading, and that the job is to find the complete picture, not just accept the one that is offered.

A friend once told me that I have the ability to take something very complicated and explain it in a simple, matter of fact way that makes sense. I have thought about that observation for a long time. I think it is the most useful thing a lawyer can do.

The law is genuinely complicated in places. Sovereign immunity exceptions, inheritance tax planning, equitable distribution of business interests — these are not simple subjects. But a client who does not understand what is happening in their own case cannot make good decisions. The job is not to demonstrate how much you know. It is to make sure the person across the table understands what they need to understand to decide well. If they leave more confused than when they arrived, something went wrong regardless of how technically correct the explanation was.

Common sense solves more problems than litigation. Use it when it applies. The law is for when it does not. And when you do need the law, being right is rarely sufficient on its own. I have watched people who were completely correct in their position lose ground because of how they said it. Judges notice. Opposing counsel notices. Mediators notice. The person who is right and calm and measured almost always does better than the person who is right and loud about it.

Being right gives you the argument. Talking softly is what makes the argument land.

Winning in court does not mean you will collect. A judgment is a piece of paper that says someone owes you money. Turning that paper into actual payment requires knowing where the debtor’s assets are, what exemptions apply, and which collection tools Pennsylvania law provides. Wage garnishment, bank levies, and judgment liens on real property are all available. None of them work automatically.

The same is true of support orders and marital settlement agreements. A court order requiring someone to pay support is not self-executing. When the other party stops paying, enforcement requires going back to court. Contempt, license suspension, wage attachment, and seizure of tax refunds are all available remedies. Getting to them requires a motion, a hearing, and sometimes years of persistence. I have seen clients win everything at trial and spend the next three years trying to collect what the court awarded them. The victory was real. The money took longer.

In over thirty-five years of practice I have heard this more times than I can count. The other side saying it cannot be done. An opposing attorney who has not done enough research. A bureaucrat who does not know the exception. A judge who has not seen the argument framed correctly yet.

Most of the time when someone tells you something cannot be done, what they mean is that they do not know how to do it, or they have not seen it done, or it is easier for them if you believe it cannot be done. Those are three different problems with three different solutions.

The answer is usually in the record somewhere. A case that was decided differently. A statute that was read more broadly. A procedure that was used once and worked. And sometimes the person who knows is not the senior partner or the judge. It is the clerk at the desk who has processed every filing for twenty years and remembers the one time someone tried it a different way. Be respectful to everyone in the building. The person who can actually help you is not always the one with the title.

My father told me three things before I went to court for the first time. Know where to park. Know which elevator bank to take. And know which way to turn when you get off, because the floors in the courthouse are laid out in ovals and if you turn the wrong way you will spend five minutes walking in circles past people who will remember that you did not know where you were going.

This was not small advice. It was the entire lesson compressed into three sentences. Preparation is not just knowing the law and the facts. It is knowing the building. Knowing the clerk’s name. Knowing which judge takes the bench on time and which one runs late. Knowing where the bathroom is before you need it. The lawyer who walks in knowing all of this looks different from the one who is figuring it out on arrival. Clients notice. Judges notice. Other lawyers notice.

The courthouse is not a neutral space. It is a place where the people who belong there move differently from the people who do not. Belonging there is partly experience and partly preparation. My father knew every floor of every courthouse in Allegheny County. I learned them from him. That knowledge is one of the things I still carry.

When I was in law school a professor asked the class to draft a separation agreement for a couple ending their marriage. The hypothetical gave both sides’ positions on custody, support, and property division. The professor said assume both parties asked you to represent them jointly to save money. Draft an agreement that works for both.

Most students drafted something. I raised my hand and said I could not do the assignment because representing both parties in a divorce is an ethics violation. A lawyer cannot represent clients with directly adverse interests. One spouse wants more custody or more property. The other spouse wants the opposite. Those interests are not just different. They are opposed. There is no way to represent both without breaching the duty of loyalty to at least one.

The professor said that was the correct answer. The assignment was not about drafting an agreement. It was about recognizing when you should not take a case at all.

I have turned down joint representation requests many times since then. I will continue to turn them down. Saving money is not worth undermining the entire structure of legal representation. When someone calls and says we both want the same lawyer to make it easier, I say no. I explain why. I refer them elsewhere if they insist. This is not a gray area. It is a bright line. I will not cross it.

A law professor told the class that legal drafting is not about knowing legal language. It is about knowing the transaction. If you are drafting a contract for a chicken coop, you need to know everything about chicken farming. How many chickens fit in a coop. What kind of ventilation they need. How often eggs are collected. What diseases spread in close quarters. What temperature control is required. How waste is managed. What predators target chickens. How much light laying hens need. When molting happens. How long a hen stays productive.

If you do not know chicken farming, you will draft a contract that sounds legal but fails in practice. You will miss the provisions that matter. You will include terms that make no sense to the people who have to live with the agreement. The contract will become worthless paper the first time something goes wrong because it does not match the reality of what the parties are actually doing.

I have drafted operating agreements for family businesses, construction contracts for commercial renovations, real estate agreements for land with access disputes, and settlement agreements that required understanding medical billing, insurance subrogation, and treatment timelines. Every single one required learning the business or transaction underneath the legal form. Not learning it from another lawyer. Learning it from the client. Learning it from industry sources. Learning enough to know what provisions will matter and which ones are just filler.

Legal drafting is not copying forms and changing names. It is understanding what people are trying to accomplish and what will go wrong if you get it wrong. That lesson applies to every contract, every settlement agreement, and every estate plan I write. If I do not understand the transaction, I should not be drafting the document.

The estate plan that fails is almost always the one where the attorney understood the documents but not the family. The will that divided assets equally without understanding that one child was running the family business. The trust that was technically correct but funded with the wrong assets. The operating agreement that had no buy-sell provision because nobody asked what happened when an owner died. Knowing the transaction means knowing what the family is actually doing and what will happen to it when circumstances change. See our page on business succession and estate planning for what that looks like in practice.

My father taught me most of what I know about practicing law in Pittsburgh. The cases, the clients, the community, the patience required when things move slowly and the judgment required when they move fast. For a long time I was assembling what he gave me. Learning which parts of it to keep and which parts reflected a different era.

I am not sure when I crossed the line from learning from him to having something of my own to add. After over 35 years I think I finally have. That accumulation, his and mine and my grandfather’s before both of us, is what walks into the room when a client sits down across from me. They may not know it is there. But it is.

I tell personal injury clients the same thing before we discuss their case. No recovery is worth the injury. No settlement replaces what was taken. A check does not undo a surgery, restore a year of lost wages the way it was actually lost, or give back the things that cannot be measured in damages.

The goal in a personal injury case is to make the recovery as complete as the law allows given what cannot be undone. That is a different goal than making the client whole. It is an honest goal. The clients who understand that distinction from the beginning tend to make better decisions about their cases.

Better this never happened. No amount of money is worth getting hurt.

My grandfather Herbert B. Lebovitz was admitted to the Pennsylvania bar in 1933 and built this firm through the Depression, the war years, and the postwar Pittsburgh that the steel industry was still defining. My father Robert continued it through the urban changes of the 1970s and 1980s. I have practiced through the digital transformation of legal services, the emergence of internet research, and now artificial intelligence that can answer legal questions faster than any associate.

What has not changed is this: the people who come to this office have real problems that affect their families, their finances, and their futures. They deserve lawyers who know the law, understand the community, and take the time to explain what is actually going on. That was true in 1933 and it is true now. The tools change. The obligation does not.

There is a question that appears on the bar exam in various forms. How many members must sit on a board of directors? The answer is always D. Read the bylaws. The law sets a minimum. The organization sets the rest. The examiner is not testing whether you know the number. The examiner is testing whether you know where to look.

That lesson has never stopped being useful. A trust beneficiary who wants to know whether they can demand a distribution needs to read the distribution standard. A family member who wants to know whether an executor can sell the house needs to read the will. A business partner who wants to know whether they can be bought out needs to read the operating agreement. The law sets a floor. The document sets everything else.

The same principle applies before any client meeting. Bring everything. Every document you have, every letter, every statement, every agreement you signed, every agreement you did not sign but wish you had. Do not decide what is relevant before you arrive. That is my job. Better to bring it and not need every page than to leave the answer sitting on the kitchen table at home.

My estates professor put it simply. The combined federal exemption was $1.2 million. You could give it away, pass it to the grandchildren through a generation-skipping trust, or leave it unprotected. If you left it unprotected, their mangy mitts would be in a Porsche too young and the grandchildren would have nothing. The spendthrift provision, the discretionary distribution standard, the trustee with authority to say no — none of that was accidental. It was architecture. The tax planning and the family planning were the same planning. The government was one problem. The heirs were the other.

I have been practicing long enough to have watched the exemption go from $1.2 million to $15 million. The mangy mitts problem has not changed.

If something matters enough that you need the other side to actually have it, send it twice. The first time is the official delivery. The second time is the courtesy copy, the one you send a few days later with a short note saying you wanted to make sure it did not get lost. Nobody takes offense at a courtesy copy. People take offense at missed deadlines, unanswered demands, and problems that could have been resolved if someone had simply followed up.

A letter that went to the wrong address. A filing that landed in a clerk’s pile and stayed there. A demand that sat in an inbox for three weeks because the person it was addressed to was on vacation and nobody was covering. The courtesy copy does not fix all of those problems. It fixes the ones that were caused by the file being deep and the inbox being full. In a practice where deadlines are hard and consequences are real, that is worth a stamp. It is especially easy now. Attach the reference file and hit send. As referenced in my prior letter of [date]. Per Exhibit 3, attached. You are not just making sure they have it. You are documenting that they had it.

The same principle applies to the formal demand letter before an Orphans Court petition. The courtesy copy is what proves the executor had the demand before the petition was filed. The same is true of a disclosure dispute after closing — the seller who can show the buyer had the document before signing is in a different position than the one who cannot. And in support enforcement, the paper trail showing the other side received every demand before the contempt motion is filed is often the difference between a hearing that takes an hour and one that takes a day. Send the courtesy copy. Attach the file. Note the prior letter. Build the record while it is easy to build.

Sometimes the first quick answer is not the best one. And sometimes the best time is later. By then the problem may have resolved itself on its own, the parties may have talked, or the urgency that drove the call turns out to be less urgent than it felt. Not every matter that comes in needs to be acted on immediately. Knowing the difference between a situation that requires speed and one that benefits from patience is part of the judgment that takes years to develop.

---

Stephen H. Lebovitz is a Pittsburgh attorney at Lebovitz & Lebovitz, P.A. Wharton economics. University of Pittsburgh School of Law. Admitted 1989. Third generation Pittsburgh lawyer. Call 412-351-4422.