Aric Press’ recent piece on lawyer retirement is excellent in identifying some of the subtle challenges for law firms dealing with Boomer departure.  Press’ Is it Time for You to Go, Joe? describes the difficult conversation faced by law firm leadership seeking to transition senior lawyers and their practices. Press goes on to observe five best practices among law firms facing the difficult conversation with the long-time contributor who needs to give way.  For any law firm facing that challenge, Press’ piece is required reading.

Preparing or planning for the difficult conversation is as important as having the conversation.  In today’s world of a large Boomer population recovering from the collapse of 2008, navigating succession dynamics with jumpy lawyers controlling business is no easy task.  Given that landscape, preparing for the conversation requires firms to consider some basics before approaching the Boomer about succession.

Timing is Everything.  Planning for succession should occur early.   But planning does not mean the conversation should be scheduled prior to careful thought on how the Boomer should be approached.  There is nothing worse than a non-strategic succession conversation spooking the Boomer into bolting to a perceived more welcome place.  For that reason, Press’ admonition to have the conversation early does not mean a spontaneous conversation just as the issue first gets on leadership’s radar.

Think About and Understand the Person.  Before having the difficult conversation, think about the person you are getting ready to speak to.  What is his or her personality?  What are his or her financial circumstances?  What kind of relationships does he or she have with clients?  What kind of relationships does he or she have with colleagues?  How profitable are his or her client relationships?  What is the track record with regards to lateral movement?

Be Flexible in Scheduling the Conversation.  If there has been adequate planning, the firm may have flexibility in scheduling the conversation for a time when the senior lawyer is likely to be most receptive.  If so, pick the right time.  Having the conversation when the attorney is on edge, feeling vulnerable or after the firm has received bad news is not preferable.

Pick the Right Messenger.  People trusted by the senior lawyer should lead the conversation.   Having the Boomer’s archenemy open the dialogue makes no sense.  Nor should the messenger be someone the Boomer does not know well.  A person respected by the Boomer and with whom he or she has a rapport is best.

The Tone of the Message Should Be One of Collaboration, not “Take It or Leave It.”   The most successful succession plans are ones that are jointly negotiated in which the needs and desires of the firm and Boomer are respectfully addressed.  Having a plan that is the product of negotiation is more likely to provide the motivators that spur the future conduct desired by both sides.  It takes time to collaborate over a succession plan, so a non-rushed “give and take” is a recipe for success and worth it for all concerned.

As Aric Press recounted in his Is it Time for You to Go, Joe?, few people relish initiating discussions about retirement with a respected colleague.  Typically it can be hard, a little emotional, and unsatisfying.  For that reason, great care is needed in planning the conversation long before it is had.  In our experience, the five basics discussed above serve firms well.  Are there others that you think are equally important?