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.

“Hooold me now – It’s hard for me to say I’m Sorry.” – Chicago

Curious what data has to say about this, but I feel that saying ‘Sorry’ more often than not when selling is a good idea. I used to think it made you look weak, but it actually makes you more relatable, human, and empathetic.  An email subject line example is: “Sorry Bob, is next week better for you to speak?” A phone example is: “Sorry if I may be mistaken about this, but…” People open up more. Use Sorry. You’ll feel more relatable. 

Playing Catch

Answering your prospects questions gives you the right to ask them questions. Timing of your questions and asking thoughtful questions are important, yet when you answer their questions, you’ve earned the right to ask. Answering their question is like catching the ball so-to-speak, then you wind up and throw the ball back, asking them a very thoughtful question. Just loading off question after question could come across as abrasive, when you instead want to come across as curious, and have a good “wind-up.” Curiosity will win the day on every call. In order to have a natural transition to ask a question back, some ‘curious’ phrases to use prior to asking your questions include “Out of curiosity,” “That reminds me,” Speaking of which,” “On that note,” “I was thinking about this before the call and wanted to learn more about,” “Curious to understand.” These help make your calls like conversations, instead of like an interview.

Are we practicing what we preach?

Salespeople understand that the more we’re able to actually speak with our prospects instead of emailing them, the more productive it will be. John Barrows speaks about this specifically with regard to negotiation, yet it’s an important rule of thumb across all types of sales conversations, including next steps, feedback, value add messages during the sales cycle, etc. (excluding logistics). Question is, do we follow the same rule when speaking with our own colleagues? Are we busy slacking or emailing important conversations to the person that sits right next to us, or do we strive to have in-person and/or phone discussions instead? Yes, not all conversations require it, but the most relevant ones do. If it has a more positive outcome with our prospects, how much more so on our very own sales teams? This creates a much more pleasant environment, resulting in more sales! A rule of thumb, I try to choose these forms of communication in the following order (1) In person, (2) Phone, (3) Text, (4) Email.  We should try and practice what we preach, and always seek to improve.