Work with a lawyer who focuses on closing the type of deals you want to do

January 09, 2026

by a professional from University of Michigan - Ann Arbor in Detroit, MI, USA

In my line of work, every once in a while, opposing counsel is a large law firm. The outcome is always the same. A recent case in point: Last year I helped a client with a minority investment. He operates a small business. His business partner wanted out. An investor wanted in. The investor had one of the largest law firms in the country representing him. While our proposed documents were clean and efficient, their redlines were not. And it was clear that a junior associate was responsible for a lot of the mark up. - Meaningless legalese was added. - Immaterial changes were made to defined terms. All this created friction. And while friction may not always kill a deal (and didn’t in this case), it can kill a deal under the wrong circumstances. Worse, I can only imagine that the junior associate was being billed out at close to $1,000 / hour. Maybe more. Do yourself a favor, work with an experienced and credentialed lawyer who focuses on closing the type of deals you want to do, be it me or someone else. Because big law is great for big transactions. But main street is a different animal.

Reply by a professional
from Columbia University in Oakland, CA, USA

In a prior life as a COO and GC, I used to take the view that even the biggest BigLaw firms are jacks of all trades, masters of none. There are specific matters that firms will be great at -- maybe because the firm has historically served clients in that market and built up expertise through repetition, or maybe because there are individual lawyers there who have demonstrated expertise in getting certain types of deals done. But no firm is good at all things, and many BigLaw firms struggle to rightsize their work for smaller matters, or even complex transactions that don't justify significant billings. I say this having started my career in BigLaw and still having a lot of friends, some of whom are outside counsel, who have remained there. When I'm on the client side today, I try to divide my work among more than one firm based on expertise. I'll try to share some perspective on how I've evaluated firms as a client over the years. The most effective way, I think, is to ask your potential counsel about the documents and process you should expect them to use. If nothing else, I find this often filters out lawyers who, for whatever reasons they might have, want to maintain some information asymmetry with the client. I can relate to not wanting to give away a lot of "free" information only for a prospective client to go to another law firm, but spending###-###-#### minutes walking through how you organize the deal process and approach document drafting or negotiation usually feels like an appropriate way for both sides to feel out if there's a good fit. At least for our firm, while significantly less than BigLaw, we don't aim to undercut the entire market on our rates. From what they share with me, most clients who work with us do so because they feel they're getting good advice when we spend time together, and I'd like to think the initial consultation is our starting place to establish that dialogue. Beyond that, asking about docs and process will also give you a sense of how your attorney organizes the process and delineates show-stopper issues vs. issues they can try to work through collaboratively with opposing counsel. Also, if they're the ones drafting definitive documents, you can sense how long their forms are. Longer documents usually incur more legal fees, but the attorney may be able to explain why they use it and how they manage costs (e.g., more robust reps and covenants that they can explain the importance of). Shorter templates can often be cheaper to negotiate, but you'll want to make sure they're not short at the expense of mitigating important risks. As a client, I don't want to have to sit with my attorney on every single materiality qualifier or low-level due diligence item, but I do want to understand the division of labor and feel comfortable knowing that my direction around risk calibration is being executed in the way I want. Docs and process are where that direction takes shape with outside counsel, so what an attorney shares about that in an initial consultation can tell you a lot. Ultimately, AI commentary aside, finding the right counsel is ultimately about finding the right fit in your relationship. Some lawyers are great at pitching and managing clients, and others are actually great technical lawyers but aren't as smooth at the non-practice elements of being a lawyer. Try to find someone who you think is competent at doing the work and communicating about it with you in whatever format feels right for how you want to manage your transaction.

Reply by an investor
from Columbia University in Dallas, TX, USA

I’ve been at a top 5 global law firm, in-house at a bank, a fund and a tech co, and am now at a regional firm. Don’t buy the brand. Interview the actual lawyer who will represent you. Find out their thoughts on staffing, solving problems, ask for data on recent transactions. There are bad and wasteful lawyers at big firms with fancy brands. There are plenty of experienced solo and small firm SMB and M&A lawyers capable of doing a great job — much better and cheaper than your average big law associate. But percentage-wise, 99% of solos and small firm lawyers are terrible or not experienced in Main Street M&A. Do your research. Check references. Get comfortable and review bills. I give free consultations and would send you across to someone else better for you if we are not a good fit.

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