Sovereign #10 - 10 Habits Of Highly Effective Cold Emailing Part 2 of 2

Welcome to Issue #10 of The Sovereign Seller. A weekly email with practical tips on how to use inbound + outbound marketing to generate leads, and get the attention of, and appointments with your most in-demand prospects.

Sunday, November 9th, 2025

7:11 AM

Indianapolis, IN

Last week in Part 1 of this series, I shared habits 1-5. Here are habits 6-10 PLUS two bonus habits!

Habit #6: Send Your Email In the Mail!

Having trouble getting response from your emails?

Tried everything else on this list and still not working?

Now it’s time to enlist my favorite platform for getting the attention of your most in-demand prospects.

The United States Postal Service!

Here’s the trick: Print out the last email you sent your ideal prospect … attach a sticky note … write in blue ink on the sticky note, something like … “I know you get a lot of emails, wanted to make sure you didn’t miss out on my offer to educate you” etc.

• Fold the printed 1-page email,
• stick into a #10 white envelope,
• hand-write their name/address,
• then hand-write your name and reply address,
• then affix a real first-class stamp on it.
• Now send it in the mail.

If you really want to get their attention, use a Fed Ex envelope.

This works. It works so well your prospect may reach out to you.

Worse case, you now have a "killer hook" for your next follow-up attempt.

This is probably the best habit/secret on this list. Make it a part of your follow-up cadence, then witness the magic.

Habit #7: Keep it ANALOG – no pictures, logos, attachments

When I say “analog,” I mean your emails should contain nothing but words.

Do not:

• embed
• attach
• insert

ANY

• logos or
• photos or
• images …
• Nothing.

I get cold emails all the time from people who don’t know my name, and somehow their email slipped through my spam filter and it's full of logos/attachments/images/photos.

Now my corporate spam filter requires I “approve” before I can open. Yet another protective layer.

Sometimes I approve these "flagged emails" just to see how bad they are.

Sometimes they're so bad they include big buttons that say “Buy Now”.

They’re asking me to buy before I even know who they are - crazy.

Anything other than PLAIN-TEXT adds friction … increasing the chance a spam filter will block you … and require your prospect to approve (an extra step) = DELETE.

Cold emails are not for selling. They’re for starting a conversation, and getting an appointment.

• No images
• No videos
• No attachments
• No emojis 😬
• No “Buy now” buttons

If you need to share a visual (like a deck, photo, or case study), use a hyperlink to a trusted storage source - Google Drive, Dropbox, or Amazon.

Habit #8: Send Your Emails When Prospects Are More Likely To Read Them - Not When It’s Convenient for You.

Salesforce built a $100M+ outbound engine in one of the most competitive markets on earth - enterprise software.

One of the key lessons I took from their prospecting playbook (documented in the great book Predictable Revenue by Aaron Ross & Marylou Tyler) is this:

Timing matters. A lot. Salesforce reps don't blast cold emails when it's convenient for them. They send when they are most likely to be read ... by busy people.

• Before 9am or after 5pm.
• And they avoid Mondays and Fridays ... the noisiest days in your inbox.
• Send on Saturdays and Sundays

Before reading that book, I never considered the timing of emails.

Or scheduling them in the future and batching my outbound email effort so I can do entire week's of emailing in a few hours.

Personally, I schedule cold emails for 7:11 AM using the “schedule-send” feature in Microsoft Outlook.

Why 7:11AM?

It feels lucky, and I like to play craps.

I also like my prospects to think I’m grinding early in the morning (and weekends) when I’m really asleep. I love waking up knowing all of my emails have already been sent.

Depending on which email service you use, right next to the “send” button locate the arrow (or icon) allowing you to "schedule send" emails.

Even for existing client emails ... I stick to this timing ... It helps my messages stand out.

Adopting a “timing” and “scheduling” strategy magnifies your selling effort, and saves you time and energy.

Habit #9: Make it Dead Simple to Book a Meeting With You

Most cold emails have one goal: Get the meeting.

So when your prospect finally replies with interest … Don’t fumble the ball.

Make it stupid-easy to book with you.

Here’s how:

• Offer 3 specific windows of day/time they can choose from
• You take responsibility for confirming a time and sending the invite

Here’s some feedback I’m hearing from in-demand prospects lately.

Busy people like it when you do the work to confirm the appointment.

So don’t get hung up on needing to automate this process using a service like Calendly.

Without the meeting, nothing can be sold. So if it takes a few emails back and forth to finalize the meeting, it’s worth the effort.

Don’t write: “What time works for you?”

Say: “Does Tuesday, Wednesday or Thursday from 12n-5p work for you?

No endless back-and-forth. Less friction, do the work for them.

Some of you may be thinking… duh. But you’d be surprised how many good salespeople forget this. (I’ve been guilty too.)

Habit #10: Use Your Signature To Educate

We’ve established several good fundamentals so far.

The signature line at the bottom of your email can ruin all of this good work.

Most sales organizations fail to optimize this valuable piece of real estate.

Worse, many require their sellers to include a branded signature with logos and other useless information.

I’m telling you to rebel against this, it's better to NOT have a signature than have one with a company logo.

Or worse - your picture!

As we covered in Habit #7, logos and photos create friction leading your email to a spam filter or instantly deleted.

You want to EXCLUDE:

• Company logos
• Your photo or any photo - any image
• Fax numbers - amazingly I still see this
• Your email address - no need you just emailed them, they can hit reply
• Phone number - up to you, but I don’t because I want an email reply. Once they reply you're in the safe zone and less likely to get caught in their spam filter.

Do use this space to make an offer.

The most advanced sales organizations embrace this real estate to work for them, and not against them.

When I was selling sponsorships for Ball State Athletics, I promoted one of my lead magnets:

That link-to-learn becomes my low-pressure bridge for prospects to learn without having to speak to me first. This gesture invites more response, appealing to people who many not be ready to buy … yet.

The net result is … this will generate more response (and more meetings) doing it ... than not doing it.

Bonus Habit #11: Commit to a Campaign, Not Just Random Emails

Your email is competing against a TSUNAMI of daily clutter hitting your prospect’s inbox.

Your prospects also have lives and kids and problems outside of work competing for their attention.

If you want to stand out, you need more than one email.

In fact, if you want to get the attention of the most in-demand buyers for your product or service - the biggest spenders - who are getting hounded by hundreds of other salespeople - you need a campaign - a multi-media, multi-touch system.

I advise committing to a year's worth of touches using multiple channels over the course of a year. And email is just one small part of this effort.

The sequence goes like this, you can find more detail via my Cold 2 Warm Prospecting System from Sovereign #4:

Month 1:

• Week 1 - Send a personalized sales letter in the mail. Around the time you anticipate the letter has arrived ... connect with your prospect on LinkedIn ... and refer to the letter in your LinkedIn request.
• About 7 days later - Call the prospect, have a voicemail script ready and refer to the value you offered in the letter.
• About 7 days after that - Send an email referring to your letter, reiterating your offer to educate.
• The rest of the month - Go quiet. This is a respectful (not annoying) effort to get busy people's attention. You are not desperate, you are systematic and creative. At the beginning of the next month, rinse and repeat, and keep doing this until they meet with you, or you decide they are no longer worth pursuing for whatever reason.

Haphazard cold outreach alone yields (on average) 1 -3 appointments out of every 100 prospects you cold email.

Committing to a systematic, multi-media system like this will triple that response - and if you stick with it for 6 months or more, you'll do even better.

But here’s the real value in having a system like this is: It frees you up to focus on the 20% driving 80% of your business - warm targets, existing clients etc.

Bonus Habit #12: How to Follow-Up Impact-fully

Here’s a common scenario … you met with a prospect, had a good conversation, you both verbally agreed on next steps but for whatever reason, you allowed the meeting to end without scheduling another.

You broke the chain of progress. It happens. We’ve all been there.

And now, your prospect is ghosting you. They’re busy, or waiting on a decision-making process, or juggling other options.

You need to capture their attention - again. Here’s how.

What most salespeople do is send another email using some combination of these words:

👉 “Just following up…” 👉 “Checking in…”

No two phrases have been uttered more by salespeople their prospects. And I’m as guilty as anyone.

I learned this from Jeremy Miner, a successful sales trainer who shares a ton of great content.

Common and repeated phrases are low impact, and low status, like this:

The secret sauce I’ve learned?

Get more detached.

Act like you don’t need the sale — like you’ve got the keys to the kingdom.

Adopt the mindset that if they don’t buy, it won’t affect you one bit — but their pain will still be there.

Try this instead:

or …

This is higher status. It’s a pattern interrupt, asking a detached type of question rather than begging for a response.

Try to eliminate “following up” and “checking in” from your sales vocabulary. It’s harder than you think. But it will make you stand out amongst a see of people “just following up”.

Thank you for reading Sovereign #10.

To your success,

Shane

P.S. I created an online video course teaching these 10 habits. If you would like to check it out for your team: https://bit.ly/10HabitsEmailingCourse​