Answer: When you are in the position of potentially having 3 job offers with two of them “A’s” and the third a “B+”, managing the timing is an exercise in patience. When you are interviewing for a VP position, the process (despite what the hiring manager says) can take as long as 6-months. The key is assisting each of the hiring organizations to move the interviewing process along. Provide appropriate information about the timing of the other two searches as early as possible. Do not wait to be asked. Provide updates as you have information to report. This is not as straightforward as it sounds.
If you are working with a retained search firm, providing information at the right time and in the right amount of detail can begin as soon as you are contacted about a search. If you are already under consideration elsewhere, you can inform the recruiter about your status and availability to quickly explore this new situation (assuming there is sufficient time to catch up.) If you are working directly with a hiring organization, you should let them (usually HR) know your status, once you have successfully completed your first round of interviews.
You can express interest and enthusiasm about the new opportunity, just as you would express that enthusiasm for each of the positions. At the outset, it is important to let the recruiter know as much as possible about where you are in the process with all of the positions you are considering. I would also recommend you provide your schedule for the next several weeks to each organization just in case that should that be needed.
There is a fine line between being overly aggressive and appropriately helpful. Always provide information in the context of being thoughtful and considerate. That enables the hiring organization to have the details “at the ready” so that your timing can accommodate the schedules of their executives. Do not ask inappropriate questions about your status. That is overly aggressive and a sign of poor judgment, which will quickly take you out of consideration.
If you are well underway with one situation and expect a decision within a few weeks, I would doubt a second or third opportunity could be explored. This is due to the complexity of the layers of interviews that would need to be arranged in order to reach the offer stage with these organizations. I would suggest that you stay in touch with the recruiter(s) to let them know your status if you do not receive an offer so you can begin to explore the other two opportunities..
The key, as you proceed through the various stages from initial interviews to (most likely) one of three finalists, is to keep each company informed of your process and timing. Do not provide too much detail about the other searches you considering. If you are expecting an offer from one company, immediately let the other two know. Since offers are complicated and terms must be understood and sometimes adjusted, it may take a few days for an offer to be extended in writing. That may prompt the other companies to extend offers or to let you know they cannot respond in time to your deadline.
If your other potential offers are going to materialize, ask each company for a specific number of days to make a decision once you have the terms finalized. If the B+ situation offer arrives first, and the other companies will be making offers quickly, arrange a final date to respond to the first offer so that you can, hopefully, evaluate the others. (If not, then decide to accept or reject the offer on its own merits.)
How these organizations respond to your situation and how cooperative and/or competitive they are, provide clues to the culture and respect they have for you. Pay attention and do not try to create a bidding situation. Be comfortable with the choice you make and gracefully exit from the other two situations. Who knows what the future may hold.