Dear Nonprofiteer, When is it appropriate to go to the Board?

Dear Nonprofiteer:
When, if ever, is it appropriate for a non-profit staff member to go to a board member with concerns about an Executive Director’s management and leadership abilities? I work at a small organization that provides services to homeless families. A new ED has been in place for six months and he is severely lacking in interpersonal and management skills. He sets a tone that is disrespectful and condescending. He also is chronically late and disorganized, creating a frantic, stressful environment for everyone else in the office. Recently, we nearly missed a major grant deadline because he didn’t get around to reviewing the proposal until the eleventh hour (despite many gentle reminders).
I am leaving my job in a few weeks – but this is a small organization with an incredible mission, and tremendous potential. I am the first to go but many others say they intend to follow — and with just 10 full time staff, this kind of turnover could do serious damage to our programs. Other staff are practically begging me to say something to the board so they don’t have to jump ship. I am hesitant to do this, and have been advising people that their only real option is to “vote with their feet” unless they have a grave ethical or legal concern. But I have no idea how long it would take for an organization to repair the damage this ED could do to its reputation and sustainability.
So what do you think, should I let the turnover speak for itself – or speak to a board member? I mentioned my concerns to one of them previously, before the current ED was promoted to his role. Clearly it wasn’t enough to sway the decision to promote him, so should I bother revisiting this or wait to see if someone checks in with me upon my departure?
Sincerely, Letting the Door Hit Me on the Ass
Dear Door:
As you’re preparing to leave anyway (rather than threatening to leave if they don’t do what you want), it would be appropriate for you to write a brief letter to the Board president outlining the difficulties you faced in trying to get the cooperation and appropriate involvement of the Executive Director. Leave it to the Board president to a) infer that you’re actually speaking for the rest of the staff as well and b) to decide when/whether/how to share the information with the rest of the Board and deal with the ED about it.
Make the letter as un-personal and un-personality driven as possible: “There seems to be some difficulty in scheduling, with staff operating on a different timeline than the Executive Director and deadlines missed as a result” rather than “This asshole can never do anything on time.”
For the same reason–accentuating the professional, eliminating the personal–the letter should go to the Board president even if there’s some other Board member to whom you’re personally closer. This isn’t a matter of personal relationships but–as you’ve pointed out–a matter of the sustainability of a valuable institution, and that means the person who needs to hear about it is the leader of its governing body.
I might also suggest that you emphasize the ED’s management difficulties rather than his interpersonal style. They may be one and the same, but what you’re really trying to do through your letter is help the Board figure out how to talk effectively to the ED about a very difficult subject. There’s never been a productive conversation that began, “I don’t like your tone;” a person’s tone is a reflection of his personality, so the only possible answer to that is, “Well, I’m not going to get a personality transplant.” On the other hand, it can be productive–albeit difficult–to say to someone, “I gather you could use some assistance in getting through your many assignments in a timely fashion–how can I help you get more help from the staff on that?”
Finally, it’s probably the better part of valor not to remind the Board president that you warned him/her and the rest of the Board that this ED would be a disaster. It’s great to be right but it’s better to be gracious!
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