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Closing secrets: Roll the dice by asking direct questions

Dailius Wilson
December 07, 2020

When we don’t hear from a prospect for sometime or we don’t get any meaningful updates, several things can happen. Some of us “panic” at the lack of clear direction and begin to over communicate, making us seem desperate and harming our chances of securing a closed won opportunity.

Sometimes we might “not want to seem rude” by respecting the time and internal process of the prospect to arrive at an outcome that is right for them. The downside of this strategy is that if we wait too long we could be caught napping with the deal slipping through our fingers. A middle ground is to ask direct questions, which gives both parties a clear sense of where things are at.

For example, good questions include:

• What are the steps you plan to follow from here in order to make your decision?
• What could I do that could put us ahead of any other option you are considering?
• Are we the firm favorite for this project? What can we do to make sure that we are?
• What stands between where we are right now and finalizing this partnership?


By asking a question that aims to reveal some of the “hidden” or less obvious feelings of the prospect, you can set yourself up for greater success.'

Don’t say you can 4 do it, prove you’ve done it before


In all sales conversations, every vendor will claim they can solve the pains of the prospect in the best way possible.

The best way to gain credibility is to showcase similar projects where you were personally involved to build trust and showcase that you are a tried and tested solution. On the surface, quoting customer names, sharing reviews or sending case studies can serve to build this momentum, but the best way is actually to get permission to bring one of your current customers on a call or to walkthrough their particular case using a demonstration.

In a deal earlier this year, I spoke with a print company in Australia who reminded me very much of one of Canada’s largest print companies. Instead of doing a product demo or slide presentation, I went through some of the training materials we made for them with the new company to give an idea of the level of detail we provide. This was a hit and gave the prospective customer more of a look into what it’s actually like being one of my clients

More closing secrets? If things are progressing well, do the hardest things early.

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