The title comes from a line by Matt Homann is his post, Ten Rules of Rainmaking. The line reminded me of a retreat I attended once that was led by Gerry Riskin. Gerry began by asking the assembled group what would have to happen that day for everyone to leave thinking it had been a great day. He spent a lot of time and engaged everybody in the discussion. All expectations were on the table. The bar was set. And then he hurdled it. He tailored what he discussed and how he organized the day to the questions he asked and how he steered discussions.
Matt’s line reminds us that clients, not the lawyers they hire, are the ones who judge the effectiveness and value of our service. Isn’t Gerry’s retreat question similar to one we ought be asking at the beginning of an engagement? Shouldn’t we be asking "what would have to happen in this dispute (or transaction, or whatever) for you to say that you believed you made a brilliant decision to engage us?" "How does ‘that end’ look to you?" The answers certainly can vary—"Go to trial and win," or "we know we have to settle quickly so get them to mediate before May 1st." And so on.
Don’t be shy about asking for financial expectations. When you first heard about the case, you had a feel for your fee. Understand that the client does too. Why not get it on the table to find out if you are in the same ballpark. If you’re thinking hundreds of thousands and the client is thinking $50,000, its qualifies as really darn important to clear that up before undertaking the engagement, lest you start down a road destined for failure. But more important than simply avoiding a potential fee dispute, it suggests that you and the client are looking at fundamentally different strategies. Why that is so would, to me at least, be of great interest. Hopefully, the many variations on this theme, understanding expectations before you can meet (and beat) them, are clear.