4 Questions to Write Painfully Triggering Cold Emails

In a world where prospects receive 3,212,108,480 horrible AI-generated emails today...

Every cold email feels like a pile of mush created by ChatGPT or your marketing team.

For a cold email to get a reply today... it literally has to trigger your prospect. It should hit so close to home that it feels like you snuck into their office and saw the exact problem that pissed them off last Tuesday.

But this is much easier said than done. I've recently helped a few Club Pass members rewrite their emails and find that their emails are either too focused on the solution... or the problem feels too generic ("most CROs need to generate more pipeline..." Duh?).

So here are 4 questions I ask every rep when rewriting their emails to make them painfully triggering:

1. What's the crappy job if you invert the solution?
2. So what?
3. Why do they have that problem?
4. How do you prevent the so-what?

And at the end, we'll roll this all into one triggering prospecting email.

(PS... read till the end)

1: What's the crappy job if you invert the solution?

Avoid focusing on what you do instead of what they hate doing.

Remember: Don't sell the drill... sell the hole.

The easiest way to figure out the crappy problem? Just invert the solution. For example:

• Call Recording Software: Coach 20x more calls? Oh, that's because you can't cover 20 calls when you're only one human being?
• Parallel Dialer: Make 2x the dials in 1 hour? Oh, so I don't have to listen to dead dial tones for an hour straight without having a single conversation?
• CRM Note Taker: Automatically update my opportunities with notes? Oh, so I don't have my manager nagging me to do 2 hours of pipeline hygiene every day?

Which one triggered you more as a seller -- the solution or the inverted problem? The problem wins every time.

Also notice, we're using dumb human language to describe the problem. Kill every single "trying to sound smart" word like:

❌ Nothing Nouns: Single source of truth, all-in-one platform, single pane of glass

❌ Vomit Verbs: Automate, centralize, streamline

Just describe the damn problem in literal human terms.

2: So what?

Now that you've got a crappy problem, you need to make sure it's a problem that matters to the business.

This is the key to prospecting into executives. Sellers make the mistake of going too tactical or too generic. A CRO doesn't care about how many clicks it takes to update your CRM... but they also go "duh" when you say they need to generate pipeline as a problem.

So explain what that crappy job means for the business. Using the same examples:

• Call Recorder: Can't cover 20 calls as a single sales manager? Oh, that means you might have key deals you haven't covered in the forecast?
• Parallel Dialer: Listening to dial tones for an hour straight? Oh, that means you have to hire 2x the SDRs to get the same output of 1 because connect rates are down?
• CRM Note Taker: Manager nagging for delayed pipeline hygiene? Oh, that means there's risk in your forecast because you're going off last Monday's data?

The sales manager feels the crappy job... the VP of Sales feels the so-what!

3: Why do they have that problem?

Reps try to research everything that could possibly be going on in a prospect's life instead of the one thing that leads to the problem.

This is the key to targeting the right accounts and great personalization. With those same examples, just ask: what does a prospect look like when they have the problem?

• Call Recorder: Sales managers can't cover 20 calls at once so there's risk in the forecast? Ah, you have more than 5 reps per manager.
• Parallel Dialer: SDRs listening to dial tones for hours and struggling with output? Ah, you have an SDR job posting to make up for the poor dial efficiency.
• CRM Note Taker: Risk in your forecast because you're going off old data? Ah, your VP of Sales is gonna have an ulcer if they talked about MEDDPICC on a podcast.

Rank your 5 triggers for each major problem and run that list top to bottom. Once you find one, write the email -- that's called the First is Best principle.

4: How do you prevent the so-what?

Ready? Watch how this all comes together in an email. Using my favorite 4-part cold email framework, let's fill it out with the solution and CTA:

1. Personalization = Why they have the problem
2. Problem = The crappy problem + so what
3. Solution = How you prevent the so-what (in HUMAN LANGUAGE)
4. CTA = Something interest-based, like "open to learning more?"

Using the CRM note taker example, here's the final cold email product:

Notice: Explain the minimum detail about your solution needed to prove how you solve the problem. All they need to know is that we use call data to update your pipeline... so they don't have to deal with the problem.

PS: Humanize yourself with a PS line with one more personalization nugget. People always read the PS and if you throw something you saw about them in the PS, they'll know a human wrote it.

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That's a wrap folks! If you liked this, we run cold email teardowns every single week with all of our Club Pass members who get access to all 30MPC courses and coaching programs for only $50 per month (until prices go up next quarter).

Check it out right here:

Club Pass: Get Cold Email Coaching!