Ask the question you don't want to ask
A friend has just left Yahoo! to start her own thing. We've been talking a lot lately about start-up life, especially hiring new people. We agreed that it is one of the hardest parts of the early stage start-up because you want to acquire resources to execute against the plan immediately, so any negative aspect of a prospective employee tends to be overlooked or downplayed. She made the comment "Sometimes you don't want to ask a question because you're afraid of the answer."
Where have I heard that before? Everywhere, not just in hiring. It doesn't matter if you are a CEO, an executive, a manager or on the front line of the company, there is a tendency in our business lives to try to steer away from uncovering information that might get in the way of our immediate objectives. It is particularly acute in sales, where there is a lot of pressure placed on sales results from the Board of Directors down. So a sales rep who comes out of a great first prospect meeting will often optimistically forecast a deal for the end of the quarter, which at that time might be 80 days out. He probably starts to realize with 30 days left that the deal is looking less likely to happen that quickly, and now has to decide what to do. Asking the obvious question "Are you going to buy from me this quarter?" is the right thing to do, but getting a negative answer has so many negative consequences personally and for the organization, it never seems timely. Likewise, managers up the line fail to ask if the "in this quarter" question has been asked for the very same reason.
Don't think it just happens in sales or hiring. As a lawyer, I saw in action a VC anxious to get one of his first deals through the investment committee failing to ask ordinary due diligence questions of the target company. There was no doubt the VC believed in the business, but it was also obvious to me during the process that there were certain things the VC really didn't want to know the answer to, like was that amazing multi-million dollar deal actually a signed contract (which it wasn't).
This post may be obvious, but I bet you've steered yourself away from getting an answer that might impede your immediate progress at least once. It is always better to have complete information, however. If you don't ask the tough questions, it is almost certain that any progress you do make will either be undone or at least waste a lot peoples' time. The test of a tough question is easy: ask the question you don't want to ask.
