Of the many times that I’ve worked on a corporate deal – not a simple agreement, but a transaction of some complexity involving multiple documents and perhaps multiple parties – it is extremely rare that the transaction got done early, in advance of the target closing date set at the beginning of the process. This is not necessarily the fault of anyone involved, but it’s a matter of deal-making being a process with a lot of moving parts that takes time. This causes some frustration, usually among the principals more than the attorneys. Although there’s no magic bullet that will cause deals to get done instantaneously, the following are some tips that will expedite the process in a manner that doesn’t cause unnecessary stress and hard feelings:

• Follow up, nicely. While job number one for you is ensuring that you are pushing out paper without much delay, once that’s done, if you’re waiting on something that’s in someone else’s hands, and it’s taken longer than expected, ping that person with a polite email, asking for an ETA.

• Schedule check-in calls. Particularly if there is a large working group, it can be helpful to have periodic conference calls where the participants go through a closing checklist or otherwise get themselves on the same page. Having the call on the calendar has the side benefit of prodding people to attend to their to-do list before the call, to avoid having to admit on the call that the work is not done. But these calls shouldn’t be done too frequently, which causes frustration, with everyone thinking they’d rather be left alone to do the work.

• Don’t showboat about off-hours work. Particularly when the transaction (inevitably) falls behind the unrealistic schedule, you’ll start to see behavior like someone emailing the group late at night or on a weekend, implying that they are sacrificing free time to work on this and wondering why everyone else isn’t as committed. Ultimately, it is unknowable what other people’s workload is and whether they’re doing as much as they can on your deal. Instead, treat everyone else as a professional, and if there are timing considerations, discuss them respectfully.

• Don’t set fake deadlines. Deal principals will often announce that a deal needs to close by a particular date, without much explanation. If, as is often the case, it’s a BS deadline that was set to short-circuit the process and perhaps limit transaction costs, it will backfire when the deadline inevitably passes because of factors that may be outside anyone’s control. At that point, the deadline-setter has lost credibility.

• Create a transaction timetable. In my experience, certain types of transactions (IPOs, for example) have a detailed weekly timetable, while others, like M&A, are less likely to have one, probably because they are too unpredictable. If it makes sense in a particular transaction, it’s good to try to impose a broad framework like this if it builds in buffer time and is more realistic than just “close by Friday.”

John Balestriere, writing in Above the Law, argues that young attorneys should not feel bound to follow the standard advice to start one’s career at a large firm to get “training.” As someone who spent 12 years at large firms and the last (almost) seven running my own small one, I’m in a position to weigh in on this topic. Although in my current position, I often expound on the benefits of small law firms, both for clients looking at what type of firm to engage and for experienced attorneys looking for a better way to practice law, I would still advise young attorneys looking to end up in the private sector to spend some time in a large firm.

First, an important caveat. Balestriere is a litigator, and my understanding (not based on experience) is that in that area, small firms and governmental agencies kind of throw young attorneys into handling trial work pretty much right away, as opposed to the large firm experience of having junior associates handle more behind-the-scenes work. I can’t speak to that; my advice in this post applies to those thinking of becoming a transactional attorney.

Most of my early formative years were spent at Willkie Farr & Gallagher, a well-regarded “white shoe” firm in New York. Although I can’t say that all of my time there was used productively (I recall with non-fondness being asked by a quirky corporate partner to not leave my apartment on a Saturday and to wait for a call, which never came), I learned a huge amount, making me the lawyer I am today. My experience at Willkie, which I think is true of most big firms, had the following attributes that, I think, make the large firm experience worthwhile for junior attorneys:

• Plenty of potential mentors – I took assignments at Willkie from dozens of partners and senior associates, allowing me to gain a variety of experiences. If you’re working at a small firm, your boss may be a good mentor, but you’re not getting the benefit of seeing how many different lawyers do their job.
• High standards – I certainly don’t want to denigrate the many talented attorneys who work at small firms and for the government, and there are some real duds at big firms, but I was impressed with the intelligence and work ethic of the great majority of those I encountered at Willkie. They helped create expectations for my work that I still seek to meet.
• Network building – By working with a lot of attorneys at a large firm (or, as in my case, at a few big firms over several years), you will encounter and hopefully impress people who may be, later in your career, potential referral sources for business or otherwise in a position to help you. Two of my most important current clients are (1) a public company whose CEO was once my boss when I was an associate, and (2) a promising startup whose founder was an associate with me at Willkie.

Gary J. Ross, like me a former BigLaw corporate and securities attorney who launched his own practice, writes in Above the Law about different types of client pitches, and which are the most effective. After detailing some lame and/or insufficient pitches, such as having gone to the same school as the potential client, he identifies the most effective pitch as being able to convince the potential client that you’ve successfully handled matters like the proposed one many times.

While I agree all of Ross’s points, there are two other elements to my pitch that I usually make:

Personal Service – Many of my clients are referred from colleagues of mine, and the client doesn’t comparison shop with other firms before hiring me, but in situations where I find myself in a competition with another firm, that firm is often a mid-sized or large firm, rather than one with my profile. In that scenario, the appropriate strategy is to play up the differences between my way of doing business versus the large firm way. Accordingly, I emphasize the personal service that I provide. In a big firm (and I speak from much experience there), the pitch meeting will often be led by the senior partner, but after the deal starts, you find yourself dealing mostly with someone more junior. In contrast, I point out to the potential client that I am the sole point of contact, though I have experienced attorneys doing behind-the-scenes work to help me keep up with my workload and be able to be responsive to the requests of multiple clients.

Cost – I’ve received advice from time to time that small law firms shouldn’t emphasize price too much, because it seems to devalue the service being offered. However, legal services are really expensive, regardless of who’s providing them. It’s perfectly valid and appropriate for clients to be focused on these costs and, accordingly, for the attorney to seek to appeal to potential clients on these grounds. Therefore, I’m not at all reticent about discussing my fees early on in my interactions with potential clients, pointing out that my colleagues and I are the same people that had successful careers in prominent firms, but whose services are now available to you at a significant discount to the going rates. I further point out that this is made possible by my firm’s extremely low overhead, with attorneys working from remote locations. In other words, when you hire me, you’re not paying indirectly for expensive artwork on office walls and summer associate trips to Yankee games.

I don’t win all pitches with these arguments – the biggest headwind that I face is that hiring a big firm is a safe choice that won’t likely be second-guessed within an organization – but it’s a pretty compelling story (if I do say so myself) and works plenty of the time.