I have worked with countless attorneys throughout my career. Hundreds? Easy. Millions? It feels like it. Across commercial, employment, litigation, commercial real estate, M&A, equity & debt financing, bankruptcy, privacy, and more, I’ve relied on counsel to help guide some of the most important decisions of my professional life. Along the way, I’ve found that only a handful stand out from the rest. The rest, commit these seven “deadly sins” that make me want to never work with them again.
The seven deadly sins of bad legal counsel from a client’s perspective:
A key part of an attorney’s job is to communicate effectively with their clients. So, meet them where they are. The best attorneys and the smartest people know how to level set appropriately to have the right conversation.
Will I, the client, know the exact statute or case law for a specific issue? No, I mean today, I can look it up with AI, but if I am spending my time memorizing things like this, I am terrible at my actual job. I may have cursory knowledge, I may know a lot, or I may have no clue.
Instead, ask me my starting point. It’s a simple: “How much do you know about X so we can start the conversation at the right place?” I am happy to tell you to start from the beginning and explain it to me like a 5-year-old, but don’t waste our time if it’s already a topic I am familiar with.
And please, for everything good in the world, don’t talk down to me. This should be a given, but it happens more often than is reasonable (and reasonable here is zero times).
This one is table stakes, and nothing will grind my gears more than a lawyer I have to chase down. Don’t make me do this. I get that everyone is being pulled in a million directions, but this should be easy, and for so many, it just is not. To be clear, this is not unique to legal; it is essential, so it’s worth calling out.
Instead, responding to an email saying, “Got it, will respond by EOD or EOW or 2 weeks from Thursday,” is worth its weight in gold. I don’t need every response to be substantive. I just need to know that you are on it and when I can expect to hear back on the issue.
But what happens next is the most important part. You actually have to do what you say you are going to do. When you respond that I will get something back in 2 days, I am going to put that on my calendar. And if I don’t hear from you in two days, I will be annoyed and follow up with you. Even if you don’t have the update you thought you’d have, let me know and then share your updated timeline.
I vividly remember negotiating a commercial lease, and my attorney took days to respond to emails and voicemails, missed the deadlines he communicated, and drove me truly to madness. I was actually pleased with the outcome, but the process was infuriating. I will never work with that attorney again, and I will never recommend him.
I will never have the same risk tolerance for a million-dollar enterprise sales deal as a couple-thousand-dollar sales deal or engaging a consultant for a $20,000 project. I also have a mental block on spending more money and time on legal issues than a contract is worth. I know the underlying liabilities and indemnifications can be greater than the contract value, but that’s the rule in my house, and it’s a risk-adjusted decision.
Do not come to me and walk through all 600 highly unlikely scenarios, and then recall the one time someone got caught out for something that we’re more likely to win the lottery than have happened for a janitorial contract. And please don’t forget that we have insurance. A lot of it, so if it’s already covered by insurance, we don’t need to fight for it tooth and nail in the contract, too.
For most things, I only want to know about the contract if there is something so wild and egregious that it warrants discussion. I also want everything to have the lightest of light touches on redlines.
Another example of what I’m talking about is for a multi-million-dollar customer, I could get comfortable with a liability cap of greater than 1x. For small, one-off customers, it’s probably not worth it to me unless there is strategic value. Also, what are we fighting for with this cap? How likely is it that this will come into play?
Please don’t take the one-size-fits-all approach. Ask me what matters up front, whether it matters universally or depends on factors, and adjust accordingly.
If you treat every risk in every contract as the same, it will be a short and frustrating relationship.
This feels in line with the superior intelligence sin. You may have seen many folks in a similar situation, but every business is unique. Yes, I know, I am going against my adage that most businesses are more similar than not, but alas, I must. There is a difference between seeing similar situations and sitting in the seat and living those situations. I won’t love it if you tell me you know exactly how my business and my job work. I promise.
Instead, earn your client’s trust with humility. I love to hear what you’ve seen in your journeys, but call out what may be different for me. And it’s okay, and appreciated, for you to say, “I’m not sure how you handle this, or I’m not sure how this works for you,” and it’s a great opportunity for me to educate you more on my business.
Lay out the top 3 or so options for me and tell me the pros and cons of each so I can make an informed decision.
I want my legal advisor to make a recommendation, but to be crystal clear, I do not want them to make a decision. I want them to acknowledge that the decision is mine to make, but great legal counsel who understands me and my business will be able to step into my shoes and say, “If I were you, this is what I would do and why.”
I am coming to you with a problem I need help solving. I want your opinion. If you just leave me with the options, well, that’s not super valuable to me. I can do the research myself pretty cheaply these days. Share anecdotes and what you’ve seen work and not work with the options.
Now, I may ultimately decide not to go with your opinion, but I will be informed, and that is what I came to you for. There is an important caveat here that this goes totally off the rails if you don’t know me or my business. Then your opinion doesn’t quite get it, and I lose trust.
Oh man, oh man, oh man. This one is bad, like, really bad. I once had a BigLaw attorney that I was paying a lot of money to make a recommendation in a very nonchalant way that, if I had not done the work myself to dig in, would have cost me over $1M. And the response when I pointed it out was “Oh, I don’t look at that, I just thought it would be easier.” Well, that, sir, gets you on my dunzo list.
It could very well be that I need to and should spend $1M on a legal issue, but call it out for me. Again, you are there to help me make informed decisions. These decisions are not just legal decisions made in a vacuum. And that’s fine if you don’t know the costs associated with it. Please just point out that there will be costs and how I should think about them.
In this example, I wasn’t very smart on the issue and didn’t even realize there would be costs until I raised it to my Board as a solution. And boy, did I look like an idiot, which brings me to my last deadly sin.
Everyone has powers that be to answer to. I am no different. Help me look good. The best attorneys think about the second-level impact of their advice, not just what they are sharing with me, but for the big issues, what does it mean for me when I have to share with my Board, my investors, or a key client or vendor?
Help me help myself and make my job easier. Yes, this requires you to understand the impacts of the legal issue, to understand who my stakeholders are, and what goals I am trying to achieve. My success is your success, and the best attorneys know this. The worst didn’t even have this thought cross their mind.
I didn’t include “have bad legal advice” because that’s the floor, not the ceiling. Every attorney should clear it, and most do. What I’ve described above is what separates the best from the rest. The best legal counsel makes my life better, and if you are in-house or outside counsel looking to up your game, I hope this is helpful.
Jessica Markowitz
COO & President, Paragon Legal
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