In advance of your trip, you should definitely do your research on this executive, including talking to as many colleagues as possible to get some background. Try to find out what his organizational priorities are, whether they have to do with corporate values or execution or quality of service, or what have you. You also want to make sure you know which specific functions this person oversees, and something about the substantive issues confronting him in his business areas. You want to understand the breadth and depth of his responsibilities and concerns so you can begin to craft ways to have a useful conversation with him.
You should also be prepared to talk about yourself -- your experiences at the company, what you're doing now, and what you'd like to be doing in the future. This senior executive may well ask you what you'd like to eventually be working on down the line, and you should have a ready answer. Here you want to be specific about one or two job areas you have a strong interest in, rather than a generic statement about simply moving up and getting promoted. And you also want to have handy a few areas of your personal life that reflect well on you and that you feel comfortable talking about -- e.g., your family, hobbies, sports, social affiliations, etc.
Once you're on the flight, take your cues from this executive about whether your conversation will veer more to the personal or to the business/organization side. And also be very sensitive to cues about which topics in either area are appropriate to discuss, and which may be too sensitive; pay attention to whether this person seems to be opening up or closing down around these topics. Finally, be prepared to be helpful when appropriate - e.g., helping with bags, holding drinks, etc. You want to make sure this executive has a good experience traveling with you, and show that you value his time.
One of my former clients was a manager at a pharmaceutical company who got an opportunity to fly from Chicago to New York with someone high up at her company. This gave her a rare opportunity to talk about her career and ideas about things she'd like to do with someone at that level. My client did her homework on this executive beforehand, and it paid off when this executive began to ask about her thoughts on the company's direction and where she'd like to be in a few years. Eventually, this executive became a mentor and sponsor to my client, and that relationship has guided her up through several levels at her company. And that trip was one of the first chances she got to showcase herself and personalize herself for this executive.
Read More Power Plays From Ron Brown:
How Can I Find Out What's Really Going on at My Company?
Help! My Boss Keeps Changing Priorities on Me
How Should I Manage a Resentful Colleague?
Help! My Colleague Is Trying To Sabotage Me
Help! My Boss Is Micro-Managing Me!
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