Most managers hate surprises. They crave certainty and surprises take them away from the primary goal of dancing attendance on their bosses.
However, life is full of surprises. That’s what creates variety and anxiety. We are all in favor of the first and hate the second.
So, how do we manage this situation? The main method is through risk identification and planning. Basically you list everything that can occur on your project and detail them to your boss. So, if they occur you can claim foresight and tell your boss it’s not a surprise, just a foreseen issue that you have to address.
Now you can have surprises on a project that cannot be foreseen. Life will throw you the odd curve ball. I remember watching a television program on the building of a new bridge across the Mississippi River; it was to replace an existing bridge that had reached the end of it usefulness. Towards the end of the project they had to pour the concrete for the road deck and, because of the heat, they had to have completed pouring it by 10 am. So, they had the concrete trucks ready to roll at 4 am and they had to cross the old bridge to get to access the opposite side of the new bridge. Everything was going to plan until a patient from a nearby mental hospital climbed up on the old bridge super structure and threatened to throw himself off it! Now we have pandemonium. The state police close down the bridge, the concrete trucks are snarled in the traffic jam, the time is passing, the temperature is rising and we have a surprise on our hands. The outcome was that the pour had to be delayed, the trucks had to return whence they’d come and they had to redo the exercise all over again the next day. (By the way the mental patient didn’t jump.)
More recently we have had the tsunami in Japan. Which, with the associated nuclear problem, resulted in a massive dislocation of the component supply chain for many multinational companies. A real black swan event, possible, but not probable.
So, shit happens and you can’t always anticipate it. But you can anticipate most of it. That’s what you have to assess and detail to your boss in advance. If he knows about it in advance then it’s not a surprise.