Bringing human skills to prospecting – in the age of AI

What are the metrics for SDR success during prospecting?

Book more meetings.

What comes on the way?

Prospects are not always interested in whatever you are selling to them.

Becc Holland, in her popular “Flip the Script” 4-session video series, walks us through skill-building for prospecting. And, yes, she puts humanity and integrity back into selling.

The sessions I found most useful are objection handling and Email Outreach strategies.

Session 1. Objection Handling

Key Takeaways:

Selling is having a human connection.

95/5 Objection Rule :

95% of the time objections are not real. 5% are real. So, how do you handle these 95% shallow objections?

Use these 6 bedrock principles when you are calling and emailing your prospects :

  1. Avoid the child ego state – don’t make the prospects rebellious by choosing the wrong words. “Happy to give you a demo”, “Let me know” immediately puts the prospect into a child mindset to rebel. Never justify, explain or defend.
  2. Pattern interrupt – break the buyer/seller dance. Be vulnerable, be unexpected – make the prospect realize they are talking to a human being on the other side instead of sounding like a pushy salesperson.
  3. Elephant in the room – show the human side and level with the prospect at their state of mind. It is not always necessary to show up with ‘extra cheerful’ way particularly when your prospect’s emotion is not matching yours. Listen to the emotional queues you are getting.
  4. Falling on your sword – take complete accountability on why the prospect is not responding. May be, your outreach is not compelling enough. Admit that. Again, be human.
  5. Mentee Chair – building internal champions – ask genuine questions. In general, human nature is to help others when they can and if they know something about the subject.
  6. Self-deprecation – put yourself on the floor – particularly useful when multiple outreach emails are going in vain. You may not get another meeting, but you will learn a lot why the messaging didn’t cut through the noise.

Session 2. Email Outreach

7 Pillars of Attractive Messaging :

  1. Prospect-Centric – only discuss prospects, not your product. Don’t even name-drop your last logo if that is not related to your prospect’s industry.
  2. Pain-Centric – What pains you alleviate, not the pleasure the product adds. I do think that if we are talking about customer pain all the time, that puts them in an unhappy state of mind. For discovery calls, teasing out pains is great, but make sure your prospects say it, YOU don’t.
  3. Pride Adverse – Make the prospect the hero/authority – it’s all about them. In repeat emails, highlight the wonderful aspects of your prospect, not your product.
  4. Fluidity – Connect the premise, body and call-to-action. This is a mistake we all do. We tend to to talk about multiple value propositions. Instead, hone in one value proposition and connect the premise, body and CTA.
  5. Relevance – Most of the time, your product is being sold to multiple personas. VP of Sales, VP of Sales Enablement, Customer Success, Sales Operations – they all care about completely different things. Even within Sales, Sales Development and Sales look for different metrics. Development leaders care about booking more meetings and sometimes influencing ACV (Annual Contract Value). Sales leaders care more about revenue – closing more deal and ARR (Annual Recurring Revenue). This is a very important point and I plan to write a future post on this. ACV actually tells more about the performance of Sales and Customer Success teams because it takes into account customer retention. Lower ACV means, you will need more customers and outreach is not enough.
  6. Brevity – Well, let me use less words to explain that.
  7. Noticeability – No Bait and Switch in Subject line pls. Sure, your open rate will increase with “Free puppies” in subject line, but what’s the point?

How to write irresistible emails using the push-pull method:

How to Write Irresistible Emails using the Push Pull Method

Key Takeaways:

Sales people most of the times are perceived as ‘pushy with an agenda’. Well, yeah – they do have to prospect, qualify and eventually close a deal. In this video, Becc talks about how to balance between push and pull when you are sending your prospecting emails.

Here is an example of Email with Pull – Push – Push – Pull strategy.

Pull – Reason for my outreach is “I loved your article” – it is all about them, your prospect

Push – What if you could do ___ with our product and get these outcomes as a result – it is your product’s value proposition

Push – If you give me a chance to unpack how we do what we do – this is your CTA – call to action for a meeting

Pull – Either way, ___ I still value your content / company / contribution – this is to demonstrate authenticity of your intention

For more tips to be great at prospecting, listen to her here. Good stuff!