Asking the extreme

I find that asking the extreme version of a question brings your prospect to conclude that your ask is not unfair at all, increasing the likelihood of any next step, including negotiations.  Questions like “Is that a bad idea? Is that unreasonable? Does that sound crazy? Is that not accurate?” brings your prospect closer to moving forward in any step of your sales process.

It’s not too late…

After you hop off the phone with a prospect, you’ll sometimes realize that you forgot to ask them an important question, like how their team is structured, or what their decision making process is, etc.  Don’t sweat it!  You can just send an email with  a “forgot to ask you” subject line, and you’ll get your answer!  In fact, their response shows you they are engaged! You can usually climb back to the top if you fall here and there. 

You don’t know…

SDR’s and AE’s sometimes feel that if they reached out to someone a number of times and do not get any response, they move on.  My philosophy is always follow up in a professional manner until you get a response one way or another.  You don’t really know what’s happening on the other end, and many times they will get back to you wanting to talk, and apologizing for not being able to respond.  It can’t hurt.  What’s the worst that can happen really?  

The isolation

I find that when you isolate the exact problem that’s preventing you from moving forward with your prospect, there are few excuses they can really rely on.  As a very specific isolation example, if a prospect has an issue with your price point, the following responses are helpful. “Just so I understand, are you saying that price is the only thing that is preventing us from moving forward?” If the answer is no, it give you a chance to see what other problems there are.  If the answer is yes, I would follow up with “So does that mean that if the price was more flexible for us both, we will be working together?”


One of my favorite affirmative responses in sales is ‘correct.’  Not very ground breaking, I know.  However, saying ‘correct’ instead of ‘Yes’ or ‘Exactly’ or ‘Absolutely’ exudes a greater form of confidence, without the need to always back up your response. In fact, when a prospect asks you if your service does something or has something specific, you’ll be pleasantly surprised to see that many times you only need to respond with ‘correct.’  There are many times when there’s really no need to go into why it’s correct or how it works. If they want to know more, they will ask. 

If you’re going to lose a sale…

When I first started in sales, a wise coach once told me ‘Charles, if you’re going to lose a sale, I’d rather you lose a sale from being completely present and actively listening than from being elsewhere and actively talking. First, your listening skills improve. Second, you’ll know how to better cater to them in the future. Third, you’ll actually learn something.’ What were one of your wisest lessons? 

thought of you…

“thought of you” — You can never lose with these words when emailing a prospect. During any part of the sales cycle, especially when the prospect is busy thinking about next steps, sending valuable content with no asks from the prospect is just good business practice. I typically will title the email subject line with “thought of you,” and the body of the email is either (1) an article you think your prospect finds valuable, or (2) new insight you’ve discovered as a firm that has nothing to do with your product, yet something they find valuable for their business. If you send them an article, for example, you better point out which specific part of the article you thought was most relevant for them, otherwise you look lazy, and probably are (we all need improvement). It makes it only about them, and they appreciate that. They come first. See more at

Ask for help!

One thing our reps have found useful for pushing deals over the fence is bringing in another senior sales person or manager who’s positioned to approve deals. This person works more closely with the finance team to finalize terms, mentioning that they work with the CFO.  We’ve found that the tone of prospective clients becomes more refreshing, knowing they are speaking with someone who’s closer to internal finance for the company, allowing for more trust and comfort.  Not to mention, this also helps reps stay on track during closing, when the stakes and nerves are usually at their peak. ASK FOR HELP!!!  

The purpose of the call

“The purpose of the call” is one of the best ways to kick off a conversation.  It gets right to the point.  On an introductory call, the first thing I say after saying hello is “glad we could connect.” Then I get right to the point, and begin with “So, the purpose of the call Bob is to first…..second…does that work for you?”  Getting to the point helps build rapport. 

What happens after that?

When your prospect is about to initiate a trial of your product, one of the best ways to ask them about their buying process is to ask what happens afterward, assuming everything goes well: “Before we start the trial, assuming everyone comes back to you at the end of the trial with great feedback, what happens after that?” This a great, open ended question that will help you understand what the next steps are after a successful trial.