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I was working with a couple of reps. last week helping them prepare for a very important onsite demo with a large prospect. They had smartly scheduled a call with an IT influencer to make sure they had their presentation and demo all buttoned up.

The sales reps. were a bit concerned going into the call that the IT influencer might not be on their team and they were going in a bit guarded in their approach and wanted to keep their cards close to the vest. As the meeting progressed, the sales reps. became more bold in their questioning and to everyone's surprise, the prospect gave us insight and information we never expected to get. He shared not only the names and titles of everyone that would be in the meeting, but also who the three key stakeholders were and what was in it for them. He shared why the last implementation had failed and the concerns about deploying a new system. He even told us who our two competitors were, not the two we thought they were!

So what can be learned from this experience?

1. You don't know if you don't ask- If you don't ask the hard and/or scary questions you'll never know what you can learn. Most prospects won't tell you who your competition is, but you won't know if you don't ask!

2. Try not to go in with preconceived judgements- There was a preconceived notion that this influencer wasn't on our team. As it turns out, he just wantded to make sure that his company purchases the best system for their needs and doesn't care what company that is.

3. Ask until you hear "No"- Once it was clear that he was willing to answer any question we asked, we just keep asking more questions. He never once refused to answer a question, so we kept asking questions until we were out of questions!

4. Don't overlook the importance of a lower-level ally- The sales reps. had never spoken with this contact, but he was running the meeting, so they decided to chat with him before the presentation. They under-estimated what he knew, and he became a very important source of information. Titles are cheap- don't assume just because the title doesn't sounds sexy that that person can't be of help to you.

The sales reps. got off the call with a new level of confidence and knew exactly what they needed to do to win the prospect team over! Go boldly forward and ask the scary questions!