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⚡ Today’s Skill In A Sentence ⚡
Automating your sales process isn't the win everyone thinks it is
Today’s Skill: Creating AI Boundaries
My fourteen year old just went down a full Terminator rabbit hole. Watched all of them, back to back and became instantly obsessed the way fourteen year olds do with things.
I'm sure he'll be on to something new in a few weeks but for now it got me thinking.
So much has changed since that movie came out over 30 years ago.
We have our phones basically tethered to us and we're already half cyborg at this point.
But that isn't the problem I'm thinking about.
The problem is what I'm watching happen in sales right now. Everyone's racing to automate every single task they can get their hands on. Emails, DMs, comments, decks, docs, all of it, handed off to the LLM of their choice with (almost) zero oversight.
One could argue it's efficient and a smart decision.
But do you know what happens when you jump into that deep end?
You stop thinking. And when you stop thinking through a problem, you stop noticing the small stuff, the actual details about your buyer that turn into stories you can use later.
Without thinking there are no stories. And stories are half of what makes you good on a call.
Then there's the second problem. None of it sounds like you anymore. Not your emails, not your comments, not your DMs. I’ve tried the “Write this in my voice” prompts, the output is pedestrian at best.
And, it's also forgettable. Just enough to be passable but it falls short with connecting on a human level, the way humans talk.
So the real question isn't whether you should use the tech.
You absolutely should. I use it too, all the time.
The question is whether you're building a better version of yourself with it, or slowly automating yourself out of relevance.
Are you a Cyborg or Full Terminator? That's the decision every founder is making right now, whether they realize it or not.
Keep These Human
Here are the activities I’d skew heavy on the “human” side.
If at all possible, don’t automate. Don’t fast track it with AI.
Cold email drafting and sending
You can use AI to brainstorm but the actual send has to look and sound like you or nobody is going to read past the second line. All of these emails nowadays have the same boring structure and same polished feel.
Add some humor, add some real research. Do something above and beyond.
It’s refreshing to read an email you know was crafted by hand. They just sound different.
Referral asks to past clients
Do. Not. Automate. This. Past clients or your network shouldn’t be added to an email sequence. They need to hear from you, in the voice they know you in. The message should be personal and thoughtful.
That also goes for reaching out to reengage past clients or leads that didn’t covert a year ago. You must lead with a very personal message.
Anything less tarnishes your relationship.
Proposal review conversations
The proposal call is where the deal actually gets negotiated, that can't happen over an automated follow up like an email. If you’re creating the proposal in AI and then using email as the main avenue to share it, you’re going about it the wrong way.
You shouldn’t be surprised when people don’t get back to you.
Discovery call questions
This is where the stories come from. You gotta be in the moment and asking deeper, more specific questions. You have to remain attentive and curious. I’m not sold on AI notetakers feeding you questions “real time”. Your communication skills are taking a massive blow.
That ends up showing up in all facets of the sales process.
LinkedIn comments and engagement
Hard no. Commenting 100 times with generic, weirdly written responses does you nothing. It doesn’t give you visibility because people can see the lack of effort. You’re not fooling many people. Plus, there’s a good chance your account gets locked for doing this.
Sidebar: While we’re on it, that’s a hard no for automated DMs too. The absolute worst thing is to act like it’s you, and pretend you are being thoughtful in your message.
Your reputation takes a hit once your comments and messages get labeled with “AI slop”.
The list above are just a handful of ways to take back control of your sales process and start thinking about ways to bring back the human element. You might have different processes or activities in your business.
Now is a really good time to analyze them and make sure you're not skewing too far away from the human connection.
My son will probably move on from Terminator in a few weeks and find some other hobby to obsess over. That's fine for a fourteen year old.
But don't let your own thinking follow the same pattern.
Once you give everything over to AI, what else is left to differentiate you from the market?
Final Thoughts
I see this pattern emerging that the first answer to any problem or frustration is “Let’s see what AI can do.”
AI is great at a lot of things but when it comes to human connection it can’t hold a candle to it.
It can’t help you have the conversation, it can’t help you problem solve live, it can’t tell stories for you and it can’t help you build trust.
All of that comes at various moments through your interaction with the buyer, whether in verbal, visual or written form.
Before you turn full Terminator and give everything over to it, stop for a minute and ask how you like to buy. How you like to interact with people.
You want to feel heard and seen. You want to feel understood. You want to feel like you’re “1 of 1”. Then give that to your buyers. Give them the ultimate experience in their interactions with you.
You can automate some of the boring admin tasks in the background but don’t automate the human connection.
It’s your differentiator now more that ever.
Action Item
Text or call three past clients this week just to check in on them.
If you don’t have past clients then someone in your network.
Just be human for a moment.
You’ll be amazed how it’s appreciated.
I’d love to hear what happened once you did. I read every reply.
Need more help? Here’s how I can step in to assist.
Need to get a quick W?
I offer one-time sessions to go deep into the specifics of whats happening today.
→ Set up a deal review audit: It’s deep-dive into active deals and how to get them over the finish line.
→ Get a sales call roasted: I review a real sales call and provide an in-depth, tactical overview for immediate improvement.
Want to build a repeatable sales foundation?
These help you build the skills and systems for the long-haul and a foundation to accelerate growth.
→ 90 Day Sales Accelerator: Hands-on coaching built around your pipeline and growth objectives.
→ Team Workshops: Live team training built around real friction points in your sales process.
→ Fractional Sales Leadership: Ongoing leadership for startups growing out of founder-led sales

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until next week!
just get started,
Brian

