It's not always just a case of bad luck or terrible timing. As Dan Pallotta explains in the Harvard Business Review, it's more systemic than that. Often, we just communicate badly and make assumptions that virtually guarantee a glitch at the last minute, when we assume things should be smooth sailing. Here are some of his suggestions for creating a more rigorous environment to avoid last mile problems:
Question everything. If someone says something that doesn't make sense to you, don't assume the other person has a handle on things and it will be all right. Dig in, and you might find that's the weak link that almost torpedoed your project.
Be especially suspect of "I think." When someone says "I think," it's often a tell which reveals that they are just guessing, or even outright hoping. Dig in here as well to figure out if there really is business risk.
Talk it over more than once. If a week has gone by, review what you think you agreed on to ensure that decisions and action items are still relevant and accurate.
Rephrase your decisions. A powerful way to ensure everyone is on the same page: Repeat back what the other party has agreed to, in a different way. That will reveal if everyone really is on the same page.
Visualize the worst case scenarios. Be sure to talk about what can go wrong throughout your project, and discuss possible mitigations and fall backs to work around them. If you really have a potential for disaster, be sure everyone understands the implications of that.
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