winstonwrites.com | Get future articles as emails
Remember that big presentation you did that time?
It was important, so you made sure it looked good. To impress people.
What you REALLY should have spent time on was figuring out how to get and keep that audience’s attention.
But that’s a difficult skill to develop.
So you focused on the things you knew how to do.
Totally normal and very human.
Except it was the wrong thing to focus on.
If you were great at getting and keeping an audience’s attention (again, a rare and difficult skill to acquire), no one would have cared that some bullets ended with periods but others didn’t.
I rewrite a lot of other people’s outbound messages. They do the same thing you did.
Writing these things isn’t even their actual job.
So when they write to you, they focus on what they DO know how to do, and what they CAN control.
Totally normal, and very human.
They stuff the message with details, hoping something will resonate.
They write things that are supposed to impress you.
They push you to engage now.
Sometimes the message ends up overworked, too clever, like this example:
End-of-year comp planning can’t come soon enough, right? I mean, who doesn’t love cutting and pasting spreadsheets for hours?
If that sounds like your idea of fun, then you’ll want to avoid XMoney’s new compensation planning tool, Comper. This tool automates the process for you, designed to eliminate manual planning.
Or the message is cold, tries to impress you and keeps pushing you.
Our carefully vetted pool of over 10000 skilled engineers and tech professionals can seamlessly augment your team with the expertise you need across your tech stack, frameworks, and infrastructure. If you’re comfortable sharing, what are the primary technologies you are currently working with? This will help us understand how we can best support you.
We take pride in our proven track record of successfully delivering AI/ML projects for startups and enterprises alike. If you’re open to discussing, how do you typically budget for external technical resources? We’re committed to finding a solution that aligns with your financial strategy.
These emails make 4 bad assumptions.
- You’re open to sudden, untested change
- No one is
- You’ll book time with a stranger
- No one does
- You like B2B humor
- Not even gonna…
- They’ll only get one shot at convincing you so they need to info dump
- If they’re only sending one email, they’re right, but that’s wrong
- If they’re only sending one email, they’re right, but that’s wrong
Let’s do this right, instead.
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By the way, I know I don’t have to tell YOU this, but don’t lie or cheat. It really doesn’t work, especially in complex sales. Does anyone really believe that second firm, above, has 10,000 people available to fix whatever your problem is? Not likely.
Instead be the first smart email the prospect gets today.

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Think about outreach messages this way.
Bragging is bad. Informative is okay. Interesting is gold.
You’re probably using LinkedIn or email to make your initial touch.
If you’re sending via LinkedIn
- Most people treat cold LinkedIn messages like an intrusion (I blame the chat format).
- On LinkedIn the need to be immediately interesting and relevant is acute.
- LinkedIn Messages need to be shorter than emails. Test this, because no one there wants to scroll to read your message.
- Sending several messages in a short time is bad.
If you’re sending emails
- Know that you can, should, and need to send several emails to the same person to make something happen. At least 3, more likely 6-12. This is a marathon and patience pays.
- Emails can be a bit longer, but make the first 1-3 as short as you possibly can. Graphics can help, but only use them if you have to. Most people read on phones and will give you just one down-swipe.
- Aim for a reply or getting them onto your mailing list (maybe with a lead magnet).
- Follow-up.
And if you’re sending either:
- Spend a lot of time on your first 20-ish words. If you’re lucky, someone will read that far before they do a gut check.
- Seriously, spend a LOT of time on your opening. Keep coming back to it like you’ve never seen it before, and see if New You is still interested.
- Use the simplest words, with the fewest syllables, that you can.
- Marketing emails come from a brand or company. Sales emails come from a person or persona.
- Neither of the examples above come from a person or persona, which is another reason they feel off as sales emails.
- Threshold is the amount of work or exposure you’re asking the reader to take on, to keep your process moving. Keep it baby-sized.
- The better your gift, offer or mechanism the better the engagement.
- Invest the most time creating your awesome opening, but invest the second most on your ‘offer’.
- Show, don’t tell. Anything you write that shows or implies instead of states is more persuasive. I’ll make another article about doing that, since showing you is superior to telling you 🙂
Extra notes:
- Getting someone to pay attention while you talk about you is hard. Getting that same person to pay attention while you talk about them is a lot easier.
- The first step to actually impressing a reader is to stop using exclamation marks.
- Anytime you can remove ‘that’ or ‘your’, do it.
- Don’t show up in someone’s life until all of your thinking and feeling, and 90% of theirs, is done.
- My first set of bullets didn’t end with periods, all the others did. You didn’t care.
- Readers skim cold emails. If it’s too clever or precious, and they have to stop to re-read, you better be saying something worth that extra time you just took from them, or they’re pissed.