'ways or red flags that would help you quickly find out if your lawyer sucks': many good suggestions above as to vetting your lawyers. Unfortunately it is often months or years after the fact when you discover that the attorneys stepped in it. They got their bill paid long ago and none of them will admit they screwed up or make it right so buyer be ware. I had a specific situation with a patent lawyer who's mistake i didn't realize until years later when another patent lawyer pointed it out and, of course, charged me to 'fix' the problem ($10k ish on top of the many $10k x 6 or 8 i had paid the original attorney over many years). Once you have hired an attorney the quickest way i can think of to find out if they suck would be to review their early work with a few experienced entrepreneurs then perhaps their lawyers. That sounds like an expensive process, but it should be a "quick way to find out if your lawyer sucks". Like most aspects of entrepreneurship, experience is your best, fastest and most reliable bullshit detector. I had the fortunate experience of working with a pretty talented general counsel in one of my corporate jobs. From small contracts to big ones to M&A and HR issues (this was a large NYSE traded software company). He had some good and some not so good lawyers on his team who i also worked with and it became pretty easy to tell the difference. My division did not get billed hourly for their time, but legal was a line item on my P&L so not using their services didn't save me anything. from that perspective i guess you could say it was free training in how to work with lawyers. In hindsight it was a great learning environment for sharpening not only my 'lawyer' radar, but also my 'legalese' vocabulary, contracts, M&A, HR, IP, legal processes, etc. Now that i do have to pay the legal bills directly i have a much better understanding of what to expect and how to manage lawyers, which is another good way to determine if your lawyer sucks. Search around your network and find a fellow entrepreneur or 2 with finely tuned lawyer radar and ask for their input. There are Lots of good, honest lawyers out there, but also lots of lousy, dishonest ones too. You don't have to settle for a lawyer that sucks. Don't expect your state bar association to filter out the bad actors - they hate to eat their young and only do so in the most egregious of cases. Contrary to popular belief, unlike many professions (doctors, contractors, insurance providers, etc.) your state does not license lawyers, the 'state bar' (the lawyers union in your state) does that. IMHO Avvo, Martindale Hubble, Superlawyers are nothing more than lawyers patting each other on the back so don't expect objective feedback there. Avvo does allow for customer feedback, but the vast majority of feedback seems to come from fellow attorneys.
like any other service provider, you need to know how to manage your attorneys. I prefer small firms (fewer than 20 lawyers but more than 2) for most work (everyday contracts, IP, HR). M&A and financing i think is more an issue of the individual lawyer. Sometimes it pays to have the 'big firm' name, but those occasions should be few and far between. Any attorney who will not meet with you and answer all of your vetting questions is a non starter - don't bother. They may be great at what they do, but if they expect to bill you for the time it takes you to determine if you want to work with them it's not likely to go well. Set very clear expectations as to what you want and what you don't want for each task - if they are the kind of lawyer you want to work with then they will want this too. For example, ask for an estimate or set a limit on the time for each task - 'hey, here's a draft of an agreement we are working on with a customer/vendor/partner, etc. Can you please review and add comments/edits and let me know if we missed any key items. Please give me a time estimate before you begin. If you will not be doing all the work yourself please let me know before you begin". As has been pointed out above, make sure you know who will be doing the work - very common to be 'sold' by the expert partner and then dished off to the green associate, who still bills at $250/hr. Go through your bills and ask questions. Make sure you don't get charged for this. If you get billed for BS ask them to credit you. If it happens again look elsewhere. Scoping hours is harder to do with M&A for example, but hopefully you will have had plenty of time to vet your attorneys before you get to that point.