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Do you talk to them over the phone, or do you see them in person? I really have to change the way to I do things in order to progress.
There's no set answer to this, and in the end, it's something you have to make a judgement call on, which is where experience will come into play. I always try to engage the prospect over the phone or email for as long as I need to suss them out and work out what stage of the buying process they are (10-15 minutes, or a couple of emails usually). I also try to assess whether we'd be a good 'fit' and whether or not I can actually do what it is they want, at a price they'll be happy to pay. If they tick all the boxes, we can spend more time talking, phone, face to face, whatever seems suitable.