What Sales Emails Taught Me About Authenticity
Jan 14, 2026
A message from Steve...
This past year, my inbox received a steady stream of emails from salespeople. Some of these check ins were kind, some were persistent, some well-intended, and many, unfortunately, were painfully familiar.
Here is a sample of some of the email funnels I kept seeing on repeat:
- “We should schedule a time to get to know one another.”
- “Checking in on you, in case you missed my message a few days ago.”
- “Let’s have a chat asap and make this happen!”
- “I haven’t heard back from you.”
- “Multiple messages have gone unanswered so far. Is everything okay on your end?”
- “Okay, this is it. I’m only following up one last time…”
None of these are “bad” on the surface, but they all share a common flaw; They don’t sound like a person who actually knows me. They sound like someone who knows a sequence, and eventually, other people offering real value get ignored because they sound like everyone else.
As leaders, teachers, coaches, and presenters, authentic connection is crucial to our success, to our team’s growth, and to our overall well-being. We should cherish authenticity and be prepared that it will cost something. It may mean we have to take a bit more time to communicate and earn someone’s business. We may come across a little less polished. We may even find we’re a bit less scalable at first. This is all part of the price of keeping it real.
In the spirit of keeping it real, when I read through this sea of seemingly mass produced “check ins”, there was a sense and a tone of intimacy that had not been earned. I share this because there was one check in (see below) that made me laugh and cringe and was the impetus for this blog. And it reads...
“I have to admit that I am starting to get
a little worried about you and your well-being.”
Well, don’t worry. I’m okay, and I trust you are okay too. But I think we can all be a bit un-okay when someone we don’t know - or a robot for that matter - tries to create guilt or false concern, in pursuit of a connection. And trust me, I don’t mind well-intended follow-ups. I respect the challenge of the sales cycle. I appreciate hard work and persistence. What I do mind, and where we should be “starting to get a little worried about you and your well-being” is when we’ve sacrificed real connection altogether and replaced it all with a mass-produced email funnel.
So, let’s do our best to keep our “check ins” real, because in a world fighting for our attention, with subject lines, headlines, and hook lines galore, authenticity isn’t just noticeable and refreshing, it’s becoming more and more of a precious commodity, and so are you.
Game On.
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