Lawyers…Quit Carefully, Says a Good Boss

There are many bosses who boast that they are good bosses. But, as was so aptly portrayed in the NBC sitcom based on the British comedy series, “The Office” (about a “terminally disingenuous  Office Manager…”*) there is very often a wide divide between how an employer  perceives himself or herself, and how the staff sees the head honcho.

If you ever have the occasion to have a dialogue with a boss who’s widely known to be fair and compassionate, however, you’d do well to let him or her have his or her say when it comes to giving you a few pointers.  On what?  Well, on anything, but most especially on knowing when it’s time to quit.

Discuss quitting with my boss, you say?  What sort of boss would want to look at things from the employee’s viewpoint?   The answer is “a very good one”.

Jay Shepherd is a self-proclaimed good boss. “I tried to be a good boss over the years I ran my lawn firm,” he says. And, judging from his recent post on Above The Law, he succeeded.  Shepherd seems to be made of the mold that has a built-in empathy gene. This qualifies him as a good boss from the get-go.

Along these lines, Shepherd has posted a bunch of worthwhile tips on knowing when to look around for the exit…and when to hold back from opening the squeaky door—you can’t do this kind of thing quietly—that leads there.

He remembers the time that a junior associate started crying when he suggested going out to celebrate her second year anniversary.   It wasn’t the prospect of a free meal that had her in tears.  No.  It was that she had been putting off telling him that she’d decided to seek greener pastures.

If nothing else, good bosses can hold a mirror up to themselves. “To be honest, I wasn’t paying her a heck of a lot, and she was ambitious,” he remembers.    He recalls that, once he got over the minor emotional blow, he could see where she was coming from. “And to her credit,” he notes, “while she was excited about her new gig, she felt sad about leaving.”

Exactly.  There’s going to be ambivalence about all good and necessary things in life. And that’s where Shepherd’s empathy gene comes in.   But looked at from an administrator’s or boss’ position, “it’s the surprise that really gets you, because you were planning a future that included that person, while he or she was planning something altogether different.”

Try to be honest, Shepherd counsels.

And when you, as an ex-boss or administrator, are confronted with dealing with your soon-to-be-ex employee, it’ll help matters oh-so-much when you run into them again, whether in the industry or at the local cinema line, if you “go out of your way not to burn any bridges”.

Another reason to leave graciously–purely from a practical standpoint–is that you may need to have a conversation about an important legal document at some point down the road.

So what, exactly, should your strategy be?  Try this, Shepherd says:   “…sit your boss down (probably best at the end of the day), and break the news gently. Say positive things (if you can think of any) about your experiences there, and then say that it’s time for you to try something new. If you’re leaving because you’re unhappy, the less said about that the better. You’re not looking to get into a debate about the merits of working there; you’re simply announcing your departure.”

“Gently”.  The word he used was “gently”.   As in “in a gradual manner or considerate or kindly.”  Compassion can be claimed—and benefited from, greatly–on both sides of the aisle.

*Per the entertainment digest

For tips on how to have that exit interview, go here:  Difficult Conversations: How to Manage & Survive the Toughest Employee Discussion 

Are you an administrator wanting to educate yourself about how to deal with returning employees?  See:  Rehiring Former Employees: Maximizing the Benefits, Minimizing the Risks

Photo courtesy of Jay Shepherd’s “Small Firms, Big Lawyers” series in Above The Law



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