My newest opportunity at New England Law | Boston (more widely known as the New England School of Law or NESL to the many denizens) is re-teaching a lesson I remember from Arthur Anderson about questions.  It’s best to ask the right questions than to pretend you have any of the answers.

Right now I am asking lots and lots of questions to figure how best to develop a successful alumni and development program at a school that has dabbled in both over its 100+ years but never embraced either as central to the mission or its future.  Much of what I’ve found is honest attempts at modest programming that resulted in equally modest results.

With a new Chairman, a great Dean and loads of unforeseen opportunity in a vulnerable economy, a shaky commercial real estate market and largely untapped alumni and friends, transformation for New England Law is a legitimate possibility.  The Chairman believes, and rightly so, that transformation is most possible if alumni step up and lead through giving, encouraging applicants who were accepted to pick New England Law, and by hiring or helping fellow alums to find jobs.

It’s quickly coming down to Money, 1Ls and Jobs.

To make significant gains in Money, 1Ls and Jobs for New England Law alumni, we need to innovate new ways of raising funds, getting applicants accepted here to matriculate and connecting alumni with appropriate jobs.  That innovation has to largely arise from how we engage our potentially most powerful constituents - the 10,000-plus lawyers who earned their degree at New England Law.

So how do we know what will lead to transformation in Money, 1Ls, and Jobs?  First, ask that question of any one of the alumni willing to answer. Figuring out who will answer and who is informed enough to answer is a piece of the puzzle, but the key is to ask and keep asking.  Answers will guide direction and engage volunteers.

Second is asking why we do the things we do on a daily basis.

When asking why, I’ve discovered that the answer is often, “That is what we’ve always done,” or “That is what I was taught to do.”  The reasons why are sometimes forgotten or not articulated.  With a clearer sense of strategic priorities, the answers to why help determine what we do with greater intensity and what to stop doing.

The last question that is critical to ask repeatedly is how. How do we help our colleagues and volunteers achieve their goals? How do we make systems serve our strategic interests? How should we deploy scarce time and financial resources to get momentum going?  This is where it is most critical to ask and keep asking the right questions.

Transformation through innovation is a greater possibility with every question that we ask.  I must remember to never stop asking or the innovation will end.