Keep it simple. Keep it short.

 I had a great coaching call with an entrepreneur yesterday. As he talked about some changes he's making in his business, I began to worry that he hadn't thought his new plan entirely through. So I asked him a question about how he intends to reach his new target market.

I wasn't interested in his detailed marketing plan. I mainly wanted to know if he discerned the same big differences that I did between his former target market and his new market. I feared that retooling his marketing strategy and messaging would be a bigger, more expensive chore than he was planning for.

But it took me a long time to make that point. Because the entrepreneur mistook my question about his marketing plan as a request for more details about the plan. I tried to interrupt a couple of times when he was too deep into the weeds, but he was just getting started and didn't want to stop.

Eventually I just had to say "Whoa." 

You're missing the point, I said. By going into such detail and never once pausing for breath, I said, he was missing a really important learning opportunity.

In all future business conversations, I suggested he start using a trusty best-practice sales tactic: when a prospect asks you a question, don't set off on a long explanation. Give the shortest, simplest explanation you can, and then say, "Can I keep going? Is it okay if I tell you more?"

That's the only way to be sure you're meeting your prospects' needs. Monitor their interest in what you're saying by asking for permission to tell them more. If you're off track, they now have a chance to say so (without seeming rude).  And that gives you a second, better chance to engage them and make sure you're answering their most important questions.

Every entrepreneur knows time is a resource. Few prospects ever give you enough time to say all you want. In fact, the bigger and more important they are, the less time they will likely have for you. So you have an obligation, to yourself and to your prospect/client/

potential ally, to keep your messages as short, clear and simple as possible. 

When you're talking, you're not listening. And the most important part of any sales conversation is what your prospect wants to tell you about their problem or your solution.

Keeping it short - and asking permission to keep going, if you truly think your answer deserves more explanation and context -- is the best way to make sure you address all your prospects' questions and concerns in the short time you have together. 

I've been on both sides of the sales dynamic, as seller and buyer, when the pitchers run out of time. It's always awkward. Prospects get frustrated because they haven't had a chance to express all their questions or concerns. Pitcher find themselves trying to save the situation by either suggesting a follow-up meeting or attempting to close too soon. Such blunders rarely result in successful deals. Mainly, they call into question the professionalism of pitchers who prefer hearing their own voice over that of their customer.

Keep it simple. Keep it short. Check in often to make sure you're on the right track. Ask questions like, "Is this the sort of information you're looking for?" "Can I keep going and tell you more about this, or do you have other issues you'd prefer to discuss?" Questions like these, that ensure you're having a conversation rather than presenting a pre-packaged pitch, inspire confidence and build trust.

My entrepreneur friend was taken aback when I called him out on for excess talking. I had interrupted our pleasant conversation to pull rank and point out where his chatter went off the rails. At first I think he was shocked that I was being so tough on him. But he was professional enough to realize I was trying to refocus him for his own good.

So I was quickly able to steer our conversation back to my main concern: the difficulties of adopting the entrepreneur's new marketing strategy. This time he gave me a concise, professional description of the potential pitfalls. And then, to my delight, he said, "Can I tell you more about how we're going to address these issues?"

Maybe listening isn't a lost art after all.