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4 Must Ask Questions Before You Click Send

Posted by Carole Mahoney on 11/3/17 11:07 AM

Sometimes when we are coaching salespeople, we are reviewing sales calls, social media interactions, and yes- even email. Wherever and however the conversations are happening, we want to know about it.

Below are examples of 2 different emails sent into us from clients, how we edited them, and why. From that came 4 questions you should be asking before you send your next sales email.

After reading them I challenge you to ask yourself- how many of your emails sound like this? How might you change them knowing what you now know?


BACKGROUND: Person signed up for free version or trial. The salesperson is not sure what emails were sent out prior to this email.

Subject: Have any <PRODUCT NAME>  questions?


How has <COMPANY NAME)>’s experience been with the <PRODUCT NAME>  so far?

I specialize in setting up business processes inside the <PRODUCT NAME> , and would love to help you get the most value out of the software.

Here are some of areas I have helped <PRODUCT NAME>  teams (over 600 to date) with in the past as a consultant:

  • Customizing the <PRODUCT NAME>  to your use case
  • Creating optimized deal funnels with tracking from stage to stage
  • Data import / migrations from other <PRODUCT NAME> s
  • Forecasting and other advanced reporting

Let's set up some time to meet. Or feel free to refer me to someone at your team this would be more relevant to.



Subject: Did your <XYZ link/download> work?

Hi <First Name>, I just got the notification that you requested <XYZ link/download>, did the resource work as expected?


First Name, Last Name



Meeting link


1- Do your research!
For example, what other correspondence has the person you are trying to reach gotten from you or your company? What is their role? Who else in their company is trying it out?

Read: How Has the Communication Pie Chart Changed?

2- Ask small layered questions.
When you rush the process and try to jump to the things you care about (scheduling the meeting for example) people put their guard up and ignore you- because you are pushy and irrelevant. In this case,the only thing we know is that they tried to download something. Did they even get it?

Read: The Art and Science of Layered Questions and Cross Examination Rules for Inbound Sales

3- It’s not about you!
Calculate the we-we factor in all your emails. Do you start off by talking about yourself, your product features, or your company? How often do you say words like; me, we, I, our? How many times do you use words like; you, yours, they, or them?

Read: Why don’t we trust salespeople?


BACKGROUND: Cold email sourced from list of competitors customers

Subject: how are things going with <COMPETITOR PRODUCT NAME>?


I'll be brief: My name is <NAME> and I'm an <TITLE> at <COMPANY NAME>. You probably receive emails like this all day, so I appreciate your time.

Was working with a similar customer earlier today and then came across your company - from there, I looked into your website and noticed you're using <COMPETITOR PRODUCT NAME> for your marketing automation efforts. If you're happy, that's great to hear. However, I would be foolish not to reach out to see if my email is timely as I've been helping businesses adopt more of an <COMPANY METHODOLOGY NAME>.  approach to help with their automation efforts.

Some common reasons we see customers leave <COMPETITOR PRODUCT NAME>:

  • Need for inbound marketing tools (SEO, Blogging, Social Media)
  • Demand to increase the number of quality leads they're generating
  • Lack of training, services and support
  • Clunky to use and difficult to set up
  • Lack of ROI reporting

If you fall into any of these categories and are open to a quick exploratory call, I would love to take 10 minutes together this week or next. Feel free to book a time that works for you.



Have you heard about <NAME OF CLIENT COMPANY>’s sales team was complaining to executive leadership about the number of quality leads they were getting?

After switching from <COMPETITOR NAME> to <COMPANY NAME>, they were able to generate more leads last year than in all of company history. You can read more here about how the CEO attributed that to record growth for the company.

Would you to learn more about how <NAME OF CLIENT COMPANY> did it?


1- Length- brevity is best.

2- It’s not about you! Calculate the we-we factor: where is the value for them?

3- Layered questions- asking for meeting too big a step in first outreach when you haven’t established value and interest.

If you feel yourself cringing because your sales emails look and sound the same way, you aren’t alone. These are common emails we encounter everyday. So if you are struggling to differentiate,ask yourself these 4 questions before you click send, post, or dial the phone:

1- What do you know about them?

2- Is it all about you, or them?

3- Is it brief?

4- Is the ask big, or small?

Want to learn more? Check out the recordings of past Live Sales Labs by clicking below.

Watch recaps from the #LiveSalesLab

Topics: sales coaching, sales conversations, sales email, salespeople