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Displeasing the Boss

Having recently joined an organization as COO, I also took on the responsibilities of interim Development Director.  One day, a draft solicitation was sent to me for approval.  I found one sentence confusing and edited it accordingly.  When asked if I wanted to see it again before it went out, I replied that as long as the edit was made, it was good to go.

I think you know how this story goes:  When I saw the piece, already published, my edit had been mangled so as to be incoherent.  At first, of course, I was angry and disappointed, but fairly quickly I decided my best course was to be curious.  "Does this make any sense to you?" I asked my staff person.  "No," she said, "But that's what you asked me to do."  The next question, "Why do you think I would ask you to send something out that made no sense," killed the conversation, but I had learned a great deal. 

The question people throughout the organization asked themselves was not whether or not they were doing good work but rather: what does the boss want?  Now, ideally there's a great deal of overlap there, but I had just seen what happened when they diverged.  As I learned in the ensuing weeks, this wasn't just an ingrained reaction to feedback, staff proactively attempted to put forward work that they thought would meet with the approval of senior leadership.

To be clear, this isn't always a bad thing.  In a small organization, with a senior leader who is a strong communicator and junior staff,  this approach can work well.  The senior leader can leverage her talents, supervise the work of others and junior staff can learn from their boss's wisdom.  

But in a larger organization, with a multi-tiered management structure and staffed with experienced professionals?  Not so much.  Here, the idea was not to simply leverage the talents of the senior leader, but also of a whole group of outstanding and committed professionals.  When staff had learned, though, to abdicate their own judgments, obviously this wasn't happening. 

There's several points here worth exploring in future posts.

  • I was managing to the work culture as I thought it should be, not as it currently existed. This wasn't fair to staff who had a clear understanding of what had always been expected of them. Managing to a culture that didn't (yet) exist, was never going to work.

  • The "what does the boss want" challenge is exacerbated when a) the senior leader isn't consistent about what she wants, b) wants things that aren't readily attainable, c) isn't aware of what is required to provide what she wants or d) doesn't know what she wants.

  • Staff were acting rationally. There were real built in incentives for pleasing the boss and disincentives for not conforming to that expectation--even if the results were better.

  • Over time staff accommodate themselves to an organizational culture, no matter how dysfunctional it may be. Asking people to change how they behave in a work place is asking a lot.

  • Particularly in a growing organization, a senior leader is likely to find that the strengths and skills that got her and her organization to that point, are no longer as useful. In fact, they may well be counterproductive.

  • Senior leaders often do have a choice between being petty dictators and enabling their organizations to grow and flourish. And that's not always an easy decision.