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One of the greater challenges of the CEO is the translation of revenue challenges into plans, commitments and expenses. It doesn't help that both your good salespeople and the bad salespeople are both lying about their sales numbers. So aside from the ultimate results, what is the difference between good and bad salespeople's projections?
The difference between a good salesperson and a bad one is usually that the good one knows that he/she is misrepresenting the projected number and by how much. The bad salesperson typically doesn't know that the real number that is likely given their efforts, pipeline and skills. So, both the numbers from the good and the bad salesperson are mis-representations. What's a start up CEO to do?
Seek specifics, be realistic, consider the process and dissect the facts.
Seek specifics: This is just about the customer, conversation and meetings details. It is about the gives and gets. What has the customer given and what has the customer gotten.
Be realistic: Unless you hear that something compelling (other than a government regulatory item like a new law -- which doesn't count or matter usually) is going to move the customer to act. Assume that it is going to take longer than it should to close the deal.
Consider the process: Compare everything you hear to the successful sales processes that have proceeded this one. If you study the way customers adopt and buy your product, you'll be able to synthesize the learnings in a way that individual salespeople are often to slow to internalize into behaviors. Salespeople are not frequently or adequately introspective about process. That's your job.
Dissect the facts: Or more directly put, try to assail the salesperson's assumptions. The salesperson's assumptions, particularly the faulty ones, will drive their results. You need to discern what is known from what it believed and from what is hoped for by the salesperson.
All of which leads the CEO to derive a personal sales forecast which is based upon facts and the reasonably expected outcome of proven process.