when is it OK to go over an unresponsive contact’s head?

A reader writes:

For nearly five months now, I have been trying to get in touch with a contact at a partner organization about some grant money they’ve promised us, by contract. Phone calls, emails — nothing. It’s getting completely absurd. I’ve repeatedly inquired as to if there’s something we need to do to hurry this along — no reply. (But he does return contacts from other organizations so I know he is alive and at work.)

This staff member is the primary liaison between his organization and ours, so we want to keep it civil. I’ve been advised to go over his head, to his boss … but she’s the executive director of his organization, and I’m very aware this could get this guy fired, maybe.

When someone’s flaking out on their essential responsibilities, when is it appropriate to go over their head to their boss? How important does the issue have to be, and/or how long should you wait?

Also, what are the best practices for going over someone’s head and getting things done, while also making sure we don’t ruin our relationship with a worker and/or organization who — for all I know — is just going through a difficult time right now?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

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