“Unless this works, I’m against it.”

In Sunday’s Mad Men episode, Ted’s partner quips, in response to Don and Ted’s seemingly-crazy plan to combine their agencies in order to win the Chevy account, “Unless this works, I’m against it.”

That phrase, and the context in which it was uttered, is a perfect microcosmic view into the relationship many attorneys have with their clients. Our job is to be the skeptic, to be risk-averse, to spot trouble coming from 10,000 miles away and lay the groundwork today to keep the client out of it down the road.  For most lawyers, this comes naturally. For those to whom it doesn’t, they either left law early on or this tendency was beat out of them in law school or in their first few years of practice.  Of course, you don’t want a lawyer who is too far in the other direction, either. You don’t want to be stuck with the lawyer who is so “creative” that he can’t even spot the risks in order to point them out to the client.

I had an experience with a client yesterday that caused me to reflect on the delicate balance that must be struck in order to be effective but not stifling. This particular client is in the finance industry. To say he is intelligent is an understatement. One of the reasons I was brought into the representation was that he wanted to do some tax structuring around an investment he is making into a fund, and the situation has some hair on it from a tax perspective.  When he came to us with what he wanted to do, I was skeptical that we could it to the full extent he wanted it done. It seemed like we’d have to work some serious tax magic, and I had my doubts.  We worked through several iterations of ideas before landing on one that we thought could work.  When we presented the structure to him, he had a series of questions and hypotheticals that really pushed the bounds of what we could do for him while still keeping him kosher from a tax perspective, but we addressed each one and explained why we needed to push back a bit on what he was requesting.

At the end of the day, we did not achieve what he set out for initially (looking to completely avoid tax on the investment income), but we ended up with a creative plan that I think will achieve the best result possible for him.  The thinking was definitely creative, and it involved a collaborative process between us and the client, rather than just us hearing an aggressive goal from the client and telling him it can’t be done, or coming to him with a solution so conservative that he ends up leaving a lot on the table.

A good lawyer is one who keeps a client out of trouble. A great lawyer is one who thinks creatively and collaboratively about solutions, and stays open to ideas that they think at first might not work. I felt like we were great lawyers here, and that felt good.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s

%d bloggers like this: