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2 Questions Top Prospectors Ask (and You Should Too)

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Written by John Doerr
Co-Founder, RAIN Group

How many times have you received a prospecting email or phone call and said, "Sure, let's meet right away?"

If you're like most of us, it probably doesn't happen very often.

If you're on the other side and the one sending emails or making calls, what's your success rate?

Probably pretty dismal.

Congratulations! You're like most of the people we surveyed.

The RAIN Group Center for Sales Research surveyed 489 sellers who outbound prospect and found the effectiveness of various prospecting tactics sorely lacking.

Prospecting Tactic Effectiveness


Notice that even 1-to-1 emails that are manually customized after thorough research are only 31% effective.

There's a lot of work to be done, and we can take our direction from Top Performers.

In the video below, I share more about how Top Performers succeed at prospecting and two questions they answer before reaching out to a prospect.



Top Performers in Prospecting Ask 2 Questions

Top Performers in Sales Prospecting have greater success rates. On average, they convert prospects to meetings 2.7X more frequently than The Rest.


By asking themselves two simple questions before they reach out to someone.

  1. Why Act? Why should the buyer meet with you? You have to position the meeting so the buyer knows they'll get something of value and it will be time well spent. Think WIIFM (what's in it for me) from the buyers' perspective.
  2. Why Now? What will the buyer miss out on if they don't take action right now? If they don't take the meeting now, your call back in 6 weeks probably won't be any different. You have to create urgency.

Here's an example of what not to do:

Hey Sam,

Last year, we were tasked with increasing demand for one of our clients, and utilized HubSpot, Linkedln, and Google ads to yield the following:

  • 283% increase in total inbound leads
  • 14% increase in total website traffic
  • 77% increase in website conversion rate

I'd love to talk through how we can potentially drive the same results at [company]. Any interest in exploring? Feel free to reserve time on my calendar here.



There are a number of issues here:

  1. Seller Centered: Notice the number of times we and our are used in that email (highlighted for ease of reading)—the focus is completely on the seller, not what they can bring to the buyer’s unique situation.
  2. Doesn't answer Why Act: The email tells you what kind of results they’ve achieved in the past, but not what value they’ll bring to the buyer during the meeting itself.
  3. Doesn't answer Why Now: There's no urgency. The onus is completely on the buyer to make the decision to click the calendar link (which, let's be honest, probably won't happen). Suggest a timeframe to meet at the minimum.

Try something like this instead:

Hey Sam,

If you can spare a quick 15 minutes, we can audit your HubSpot account and provide you with actionable updates to increase lead flow to your sales team.

My team at [Company] specializes in achieving top-line growth for our clients, and we're a HubSpot Partner, so we have a much deeper understanding of which levers to pull and when. You can read more about our HubSpot qualification here if you'd like.

Based on a quick analysis, it looks like your competitors, X and Y, are already taking advantage of HubSpot features that would benefit you. Are you free next week so we can get the ball rolling on looking at these for you?



This email is much stronger. It not only has a better mix of we/you language, but also answers Why Act? by providing the value-add offer in the first sentence, and Why Now? by suggesting others in their space are already implementing the same tactics. Beyond that, this email also answers Why Us? and Why Trust?, the other two questions used to build a strong value proposition.

If your prospecting efforts aren't working, stop selling your product or service and start selling your value.

In all your outreach efforts, lead with new ideas and possibilities. Bring something to the table where the buyer can say, "Yes, I can see the value I'll get from that meeting and want to meet with you."

And don't forget to answer Why Act? and Why Now? in every prospecting message.

Download: 4 Steps to Fill Your Pipeline with Quality Opportunities Guide
Last Updated August 21, 2023

Topics: Sales Prospecting