Good commercial lawyers have a thorough understanding of the industry, the transaction type and the area of law that they advise on. They have done deals like yours before and give specific examples of things that go wrong in practice and how to avoid them. Good commercial lawyers are happy to refer you to someone else when they don't meet these criteria. Bad commercial lawyers try to do every piece of work that comes up for a client and talk in generalities rather than specifics.
Good commercial lawyers listen closely to their clients and understand their approach and motivations for each deal. They vary their approach to match the each client's situation, leverage and appetite for risk. Bad commercial lawyers replicate the same formula every time.
Good commercial lawyers prioritise the points they raise in markups and negotiations. Bad commercial lawyers try to negotiate every little issue. Then at the end in order to get a deal done, they have to make large concessions.
Good commercial lawyers make proposals and draft clauses which the other side might actually agree. Bad commercial lawyers make one-sided proposals which protect their client but which the other side will never agree. This inevitably results in further rounds of negotiation. Good commercial lawyers ask the right questions and listen carefully to the other side in negotiations. This enables them to identify what the other side might agree to. Bad commercial lawyers use up all the oxygen in the negotiation arguing for their initial position.
Good commercial lawyers think hard about each problem, and then think hard about possible solutions and the best way to respond. Bad commercial lawyers focus on the problem and react emotionally.
Good commercial lawyers have hard conversations with their clients. They will persuade you to do something you don't want to do (or not do something you want to do), when it matters. Good commercial lawyers use their knowledge of the industry, transaction and client to know when to do this. Bad commercial lawyers say yes to everything to try and keep the client happy.
Good commercial lawyers try to give realistic predictions to you about cost, timeframes and what the other side will agree to. Even though this is difficult. Bad commercial lawyers avoid being tied down.
Good commercial lawyers are in the trenches with their clients on each deal and take ownership of outcomes. They are prepared to take the risk of advising in support of positions or deals. Bad commercial lawyers cover their ass.
Good commercial lawyers provide specific actionable recommendations at each stage of the deal and stand behind that advice. Bad commercial lawyers avoid taking a position and just identify the risks and downsides of every option.
Bad commercial lawyers never agree to any drafting proposed by the other side. They argue with the other side's lawyer every time and insist on their own language. Good commercial lawyers find things they can agree to and move deals forward to completion. They aren't precious about their own drafting and can adapt, respond and vary clauses in response to feedback.
However, good commercial lawyers do forcefully (but respectfully) argue with the lawyer for the other side, where it is important in the context of the deal. Bad commercial lawyers are afraid to take an assertive position, unnecessarily dragging out negotiations.
Good commercial lawyers spend their time negotiating and looking for solutions. Bad commercial lawyers spend their time writing lengthy written comments about the risks of what the other side has proposed. Bad commercial lawyers also spend a lot of time on negotiation tactics to try and "win" agreement to their one-sided proposals.
Good commercial lawyers provide support and guidance to clients beyond the scope of the legal advice on specific matters. They use their industry and transactional experience and networks to make introductions, recommend other advisers and make non-legal suggestions that benefit their clients' businesses. Bad commercial lawyers take their clients out to lunch once a year.
Good commercial lawyers are always looking for ways to help you do deals quickly and more efficiently, even at the expense of short term fees. They embrace opportunities to use technology or work with other service providers where this is in your interests. Bad commercial lawyers protect their patch and resist any change to the way they have always done things.
This post is inspired by Ben Horowitz's famous 1996 article Good Product Manager/Bad Product Manager, also included in his book The Hard Thing About Hard Things. Like product managers, commercial lawyers have a complex role where expectations and accountabilities are often poorly defined. Contrasting good and bad can be a useful way of fleshing that out.