Ask HN: Tell me your good and bad experiences with lawyers | Hacker News Reader

Ask HN: Tell me your good and bad experiences with lawyers

20 pointsjd_illa28 comments

I'm an attorney interested in starting my own practice. Probably will start with corporate, financing & M&A work for tech startups since that's my experience, but I'd be open to branch out as I learn more. I was surprised to learn very few attorneys do user research before opening their own shop.

(Unlike many lawyers,) I actually like practicing law and helping clients problem-solve. Would like to build a practice that serves as a solution, not another problem.

So tell me: what bad experiences have you had with lawyers? What about the good ones? If you're a founder, what is something you'd like to tell the legal industry?

Share/vent/spout off as you please, but be civil and please don't mention specific names!

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Over 30 years ago when I was starting out as a consultant I wanted a lawyer who'd give a cursory review of contracts I was given for a fixed price per page.

I started interviewing lawyers. My standard question was "will you sign a contract for your services?". Most of them said some variant of no, although there was the one who accused me of being part of some bar investigation.

So one of them said "if you draw up the contract I'll look at it". Seemed reasonable to me! He stood up and came around from behind the desk to shake hands, at which point it became apparent that his feet were bare. Our relationship lasted for over a decade.

(Then there was that time in the cadillac driving through the drainage ditch while the bailiffs held a lawyer's head out the open window in the spray, but we won't discuss that.)

Please, I must hear the Cadillac story. You can’t just drop that casually!

I second this!

note to self: don't wear shoes.

Get a good carpet. I noticed the carpet. The carpet was the most ostentatious thing in the office.

So, my wife is a lawyer, and I'm sure she's got lots of her own stories about bad lawyers. But I only have one such story, even though I have literally met hundreds of lawyers over the decades that my wife and I have been married.

I was called in for jury duty. A large pool was assembled, for what was to be a personal injury case. Several classes of people from the pool were dismissed before any of the potential jurors were to be interviewed -- any uniformed police officer or military person was excused and thanked for their service. The former dean of the UT Law School happened to be in the pool, and the judge recognized his name and excused him as well (I thanked him for his service). That left the rest of us, about half the initial pool remaining.

They then proceeded to start explaining parts of the case. The lawyer for the plaintiffs versus the lawyer representing the defendant as well as the lawyers of the insurance company for the defendant. The lawyers for the defendant and the insurance company led off, to be followed by the lawyer for the plaintiffs.

Everything started off with a relatively factual explanation of what happened, and what the basic claims were. Then the plaintiff lawyer stepped up. About every other sentence, he would say something that was factually incorrect or was a matter to be decided by the case we were there to hear, and the lawyers for the other side would say "you can't say that", and the judge would agree. Or the judge would step in first and say "you can't say that". This repeated time after time.

I noticed that the plaintiffs were wearing brand new jeans and t-shirts, not even washed once. It seemed obvious those had been bought that morning.

After a lengthy explanation from all the lawyers involved, the judge addressed the members of the jury pool and said "if there is any other reason why you are unable to serve on this jury, please speak up now." I held up my hand, and the judge called me forward.

I approached the bench, and I was a little surprised that so did the lawyers. Especially the lawyer for the plaintiffs. The judge asked me why I couldn't serve, and I said "I have developed an intense personal dislike for one of the counsel." The judge seemed quite exasperated, and asked if I felt that this would impact my ability to be impartial to the case. I confirmed that it would.

The lawyer for the plaintiffs then said "may I ask which attorney it is that you have developed an intense personal dislike for?" To which I kept my eyes aimed straight at the judge and responded "with all due respect sir, I don't think you want me to answer that question". The judge then excused me.

As I left, I wanted desperately to warn these people that this douche bag was the worst kind of ambulance chaser, and that they really needed to fire him and get a better lawyer. But I didn't.

So, if you're going to be a lawyer and practicing in a court room, I would ask that you work very hard not to be that douche bag.

interesting story! I'm a transactional attorney, not very familiar with plaintiff attorneys in court but there are clients who really like aggressive plaintiff attorneys! And there is plenty of predatory players in the field as well.

Positive experiences - Patent lawyers at one company were just plain easy to work with, and took the time to explain why they were filing the patent a certain way. They didn't put too much burden on the inventors. Overall it wasn't much effort for me and my coworkers and I understood what was happening. I think they were company-internal lawyers - Having a contract lawyer review a basic contract for software development was a good experience - they were quick, professional, and responsive. I remember being uncomfortable doing remote contract review at the time (around 2015) and it's funny how the times have changed - Being prepared for a deposition was a good experience and they took the time to teach me a lot about how to disagree in a cooperative manner - Chatting with a contract lawyer about delays in signing deals was always useful and taught me a lot

Negative experiences - Patient lawyer consultant at another company was just ok, they put the burden of strategy on us and any time we asked for advice they would flip things around and ask what we wanted to do, but high-level direction wasn't enough for them - Legal team inside a previous company would swoop in out of nowhere and raise a stink about every little thing. When we included them early on projects, they'd take it as a sign to try and meddle with every little detail and often delayed projects or led to them being shelved indefinitely. It would've gone a lot better if they just spent time to make sure we were informed about legal risks enough to make tradeoffs, but they were pretty heavy handed. In later years it got worse when they started to step on PMs and other leaders toes about overall feature designs and product designs. Like things that didn't have legal implications at all.

Another thing which is missing is in the area of employment law, particularly as it intersects professionals who also consult. For instance I work on open source software, and there's usually little or no recognition of this in the typical employment contract.

For instance I used to have a "tools of the trade" addendum (that I worked up together with the barefoot lawyer over several years) but that was before "open source" was much of a thing. It'd be worth several hundred dollars to me to have timely, pertinent boilerplate for that.

Or, there was the situation where an employer took VC money and wanted everyone to sign new contracts. I hired the lawyer they'd want... if they were hiring a lawyer locally. (He wasn't on retainer with them, so that was good intelligence to obtain.) I paid about $700 for the advice that "this contract is an intelligence test: if you sign it you're too stupid to work there". So I followed my lawyer's advice; I suppose it worked out as well as it possibly could have.

interesting, I'd love to know more about the employment-open source gap if you'd be up for sharing more!

I am not a lawyer. ;-) But I am reasonable. I don't like poker; but I have a good poker face. Something the barefoot lawyer drilled into my head was: stay out of court! I look at contracts that way. A hohum contract which has indisputable clarity is preferable to one which seems like it might go your way in court. In general, most employment contracts seem to lack that clarity.

It's difficult if not impossible to separate open source from consulting. Then there's this notion of "fiduciary duty" which mostly gets ignored. A lot of companies don't seem to be able to define what it is they do in a way that it seems to me would stand up in court. Even if you try really hard, there aren't that many ways to compare the contents of two arrays. How many companies are really "devops companies"? How many hire or contract devops engineers? How is that distinction drawn?

Seems to me that clear practices for compartmentalizing and handling open source and identifying potential open source candidates are lacking. I've been told that my contract doesn't allow me to report bugs upstream: do I want to test that in court? Is it reasonable for me, as a professional who damned well knows better to claim that a string compare is an original work? [0] Does that impugn my integrity, in court? Does "open source" augur professional standards which should be upheld, in court? If someone hires me, knowing that I profess to hold to certain professional standards, demonstrated by involvement with open source, and the contract suggests otherwise, which way will that fall in court?

"Tools of the trade" addressed a somewhat different concern: clients and employers who would prefer that the code wasn't openly published, even if it was acknowledged to embody such a tool. (This was actually a big one.) I'm not convinced that that concern doesn't still have some validity (although not submitting bugs upstream "because opsec" my ass).

Suppose a contract says that any open source I am involved with and I use in conjunction with performance of services therefore grants to them some "rights"? What if I'm not the only contributor? What about the ironclad limitation of liability which is part of the open source license?

[0] I wrote the Zen InterSLIP Dialing Script. Some time later received communications from a publisher in a lather because it had been included on some CD included with some book. I stated numerous times, in numerous ways, that in my opinion it didn't reach the level of originality which imbued it with intellectual property protections.

You're welcome to stalk me and reach out if you want to continue this convo. rgds...

The tax and real estate attorneys I've had have always been mostly pleasant. They have a limited responsibility and seem to enjoy doing it (closing on properties, fixing tax issues, etc.).

My only negative experience with the legal side is actually with law professors. I took a couple of law classes as filler in undergrad work, and these guys were the worst. Not only just bad professors, but also very arrogant. After following a few of them on Twitter after the fact, I don't think it was just my very small sample set either. They seem to be terrible, miserable people.

I did have a couple of professors I loved, but I overall agree with this, which is sad. Law professors tend to be really out of touch with the practical side of the profession. That plus the socratic method makes legal education more about fear-mongering and stuffing knowledge in your head than learning how to be a good lawyer to clients.

Finding a lawyer when you have no idea what it is you even want to do. Nobody in my family has ever had to use our own lawyer. When we did our immigration stuff it was done by my dad’s employer.

I tried to find some lawyers to ask questions about starting a company and understanding some of the legal implications. Literally nobody replied to me when I left a voicemail for consultation request. It left me with a really poor experience and I ended up YOLO’ing with Clerky.

Wouldn’t mind if anyone has some advice here. Everyone I talk to this about either comes from a family that’s loaded and everyone’s got their lawyer on their cell phone like it’s their buddy, or has lawyers in their family.

My wife is a lawyer.

Lots of people in my family, or my wife's family, will call or e-mail or text her, for legal advice. My wife is not an expert in any of these areas, but she has a JD, she is on the DC Bar, the NY Bar, and the Texas Bar, among others. She has practiced law in many countries, been the General Counsel of a large multi-billion dollar international company, and came very close to being certified as a UK Solicitor. She's also smart enough to know when she's out of her depth. She can also use Lexis-Nexis.

She also says that one of the biggest mistakes that most lawyers make is hubris. Plenty of lawyers will take on cases or clients for which they know absolutely nothing, but they will be supremely confident that they can handle anything.

Frankly, the biggest thing my wife does on these matters is to act as a sounding board, use basic logic, general knowledge of how the legal systems tend to work in various jurisdictions, and having a large pool of other lawyers to whom she can refer people if things get serious. And if no one in her pool of lawyer friends and co-workers at her firm can help, then she knows the tools to use to go find other lawyers outside of her circle. As a former General Counsel herself, she is well versed in the tools of how to find good outside counsel.

The key is to know what you're good at, when you're out of your depth, and know how to find help from other experts who can fill in those gaps in your expertise. And to have a big network of friends.

Thanks for this! What tools does she use, other than her network and Lexis-Nexis? I'd love to be able to access those. In terms of hubris/specialty, that's a great point. Law can be really specialized but unless you're in a big firm, it can be hard to find good specialist legal partners, so learning how to tackle new topics (while acknowledging your limits) is a critical skill.

Another main tool that I know she uses is called Practical Law. It's another website, but I don't know if it's from Westlaw or Thomson Reuters. I know that she led the effort to get her entire firm on the system, and she was able to get them a substantial discount as well. But that contract does have to be renewed every year.

thanks!! Yeah I'm aware of them, they're so expensive tho! Probably worth the price.

The price per person goes down as you get more people signed up.

But at the individual level, I don't think even my wife would be willing to pay that price. You need to get larger groups of people together before it starts becoming compelling enough.

The biggest thing is that people expect lawyers to be deep experts, and for the "justice" system to be just.

I've found that many lawyers have limited knowledge on the deep details or just can't spend the time to explore those defenses or novel defenses. They pretty much operate on a pattern of their past cases. For example, a vaccine injury lawyer doesn't want to look into the statistics of how common a rare injury when preceeded by a vaccine vs not. In a civil court where decisions are supposed to be based on "more likely than not" standard, showing the likelihood can make a huge impact. Or in another case the lawyer I talked to missed a couple of issues with police/prosecutor conduct which violated the rules of procedure, and missed a precedential ruling that would have been applicable to the case.

Client expectations can also be high regarding fairness in court (assuming litigation is potentially involved). Going back to the "more likely than not" standard, protection from abuses and red flag laws are abused. This is trivial to prove out statistically as the number of orders which are later reversed or not extended are grater than 51%, and that the overwhelming majority of the subjects they are served against have no history of abuse, evidence of abuse, nor did they abuse the person during or after the order (it's just a piece of paper afterall). Another example is when our rights were violated the lawyer we talked to said it was a violation but there's not a good case because the judges only care if there was significant financial or physical injury involved.

So doing things to manage client expectations could be good.

I haven't had many experiences with lawyers, thank God. But the ones I had have been mediocre. The whole system and experience has been a major let down from the stuff you're taught in school/society about justice, integrity, etc.

> Another example is when our rights were violated the lawyer we talked to said it was a violation but there's not a good case because the judges only care if there was significant financial or physical injury involved.

It’s not that judges don’t care, it’s that courts are there to provide a remedy where one party has injured another. If there is no actual injury (damages in legal parlance), then the court has no power to provide a remedy.

Although just practically speaking oftentimes in these situations the expense of a lawsuit dramatically outweighs any potential compensation. Judges tend to view those cases as a waste of their time because the plaintiff is usually just trying to make a point or to punish the defendant rather than seeking meaningful compensation. It’s basically lighting a big pile of cash on fire to make someone feel better. Most judges believe the courts aren’t there to act as platform for grand standing or moralizing or punishing wrongdoers (at least in civil suits without punitive damages). The court system is already overloaded just dealing with more substantive cases where injured people need to be made whole in a significant way.

"It’s not that judges don’t care, it’s that courts are there to provide a remedy where one party has injured another. If there is no actual injury (damages in legal parlance), then the court has no power to provide a remedy."

The court could enjoin the state police from continuing their policy and practice of allowing troopers to knowingly hold an incorrect charge against someone, especially when that charge has restrictions in one's freedoms that the correct charge would not. And we would absolutely want some punitive damages for such brazen oppression and the extreme inconvenience that was force on us to modify our daily lives.

"The court system is already overloaded just dealing with more substantive cases"

If they don't have time to deal with rights violations, then they shouldn't have time to enforce the original (minor) offense either. Just drop the whole fucking case, that would have been the best thing for everyone, but they're too focused on winning at all costs.

this is really helpful, and sorry to hear about your mediocre experiences.

The most annoying lawyers are the ones with husbands that start every comment with “my wife is a lawyer . . .”

Hopefully this comment is helpful to fellow entrepreneurs as well.

Learnings From Working With Lawyers

- You Need to Manage Your Lawyer, Not The Other Way Around

Your lawyer often will not understand the priority of a business issue or the impact that a delay in resolution can have on the business. It is your responsibility to explain that to them AND have them get it done. With multiple clients, you are, in reality competing for your lawyer’s time. Just because you are paying them well does not mean they will get it done on your schedule. Don't expect that.

- Tell Them Everything, No Matter the Situation

The more your lawyer knows about the business situation, the context, your concerns, your goals, the more a good lawyer can determine the best solution. There are typically many available solutions for a given problem, or many ways to negotiate a contract, the more your lawyer understands the sensitivities of the issue at hand, the better the ultimate outcome. And if your response to this is, I don't trust my lawyer, you need to find a new lawyer.

- Don't Be Afraid to Make Suggestions or Modifications

While they are experts in the law, they again are not necessarily experts in the situation. You have every right to redline your own lawyer's contracts with typos, word choices, or comment if something doesn't approach the business problem the right way. Just like in any requirements gathering process, you need to own the output from a business standpoint.

Suggestions for Lawyers

- Deliver What You Promised, When You Promised

What everyone is looking for when hiring a service provider of any kind is certainty that the job will get done. If you said you would send it first thing in the morning, send it at 9am PT or earlier, not 12pm PT. If you said you would follow up with questions before moving to the next round of negotiations, do it without needing to be asked twice. If you have run into a challenge, disclose it as soon as possible versus waiting until the next meeting. The sheer number of times I have had to remind lawyers that they owe me something or they are late on a deliverable is far too high for a high paid profession.

- Better Delineate What is "Market" and What is Negotiable

Most of the time in contracts there are certain things that are not negotiable or have to be in there for a certain reason. Don't lead your client down the road of negotiating on those types of items. It wastes everyone’s time and while it may help your billable hours in the short term, you will burn trust in the long term. Founders rely on you to understand what is negotiable / market / fair. Be that voice, especially when a founder is trying to negotiate something that will ultimately make them look foolish for negotiating on it.

- Invoice Timely and Accurately

While it seems basic, invoice items timely along with a brief description. Don't assume that founders will remember why you spent 12 hours negotiating an "NDA". As you build a relationship of trust, this can be more high level. But the number of times I've gotten duplicate invoices, or invoices with descriptions that are wrong or that seem out of bounds is far too high.

My wife is a lawyer. One of her biggest complaints she has had over the years with certain clients has been that they want to treat her like their therapist. But that's not what you're paying your lawyer for, and that's not what they're good at.

So, your lawyer should be your lawyer, and your therapist should be your therapist.

i actually don't mind playing the therapist role! so many people come to lawyers when they are overwhelmed or in a bad spot. If you can help them out, whether that's by actually solving the problem or by being a smart/aligned sounding board, that's a huge bonus. A lot of lawyers don't like playing that role though (understandably so, since it's not technically "part" of the job).

this is super helpful! are you an attorney? I'd love to connect if so!

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