Imagine a protracted negotiation with a challenging customer. Your firm is clearly in the wrong, yet you know it's your responsibility to take the firm's side and hammer out a compromise. You labor for days (perhaps weeks) attempting to get the best possible deal you can without violating the (stated) governing principles of your firm. At the end of the negotiation, you have a compromise -- one that is hard-fought, and certainly the best you can do.
But when you step back and look at it, it's pretty clear it's going over like a lead balloon with your boss. The compromise is expensive, ugly and perhaps inconsistent with the boss's image of the company.
How do you sell the deal, get approval, and move on with life?
At this point it probably isn't valuable to point out that you should have been keeping your boss in the loop all along. When the boss understands the pain experienced to reach a compromise, he/she is much more likely to accept it. But what if you failed to loop her in? What then?
I recommend a two step process, the first one involving a little influencing, and the second one consisting of taking your lumps and being patient.
In the first step, you have to identify the most likely person your boss will lean on for advice when faced with approving or scuttling your deal. With most of my bosses, this was a predictable and repeatable person -- in one company it was the CFO, in another a subordinate, in a third a corporate staffer. Once you know your target, you should schedule a meeting and go through the details of what got you to where you are now. Listen to advice or thoughts -- these same items are likely to come up when you talk to the boss about the situation, too -- and it will give you a chance to think through your responses. In the end, ask for help. This won't always work, but most senior people can't resist an earnest request for aid.
After step one, you'll have a pretty good idea what the boss might object to, and how he is likely to react. With a little luck, you'll also have a quiet ally who can help sell your compromise. Your influencer may or may not say something to the boss prior to your meeting, be prepared either way. In my experience, the influencer's preselling won't make things more difficult unless you've crossed a line, or are about to hit one of the boss's hot buttons.
Then comes the big meeting, which is likely to be unpleasant and uncomfortable. When hearing the "coulda, woulda, shoulda" don't get angry, but don't just roll over and give up either. In parallel apologize, and explain (when you can) why you did what you did (or didn't do) what the boss thought you should do.
Ideally, you'll get through all the explanations, and the boss will realize your compromise, while not the best conceivable outcome, might be the best possible under the circumstances.
But don't count on it.
Most likely you'll be sent from the room early leaving an angry boss, an unfinished story, and possibly instructions to undo all your hard work -- but don't move too quickly on this last point.
This is where completing the first step can save you. When the boss goes to his/her confidant, they are likely to act as a voice of reason in the roilling sea of emotions. With a little time, the boss will usually come around and accept your compromise as the best one under the circumstances.
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Non-Fiction: NAVIGATING CORPORATE POLITICS (released 7/19/12)