March 28, 2026 | Read online
Back in 2017 I went to Gary Vaynerchuk’s office for one of his 4D sessions.
It was a small group of entrepreneurs sitting in a room with his team as they walked through how they were building brands and leveraging social. At the end, Gary came in and opened it up for Q&A.
Around that same time, a few reps I had trained at Salesforce reached out to me. They had built an AI tool that could write hyper-personalized emails based on my “Why You Now” framework. I didn’t believe them at first. I asked them to send me an example.
When they did, it honestly caught me off guard. It was better than anything I could have written myself, and it did it in a fraction of the time. Remember, this was back in 2017 before all this AI hype hit.
That was the first time I had one of those “this changes everything” moments with AI.
So when Gary came in, I asked him about it. I told him I had just seen a robot write a better email than I could and asked him where that left me as a trainer and us as Sales professionals.
His answer has stuck with me to this day. He said, “Don’t worry about the tech. You’re not going to beat it. Beat the last mile.”
I didn’t fully appreciate what he meant at the time, but I do now.
The tech is always going to get better. It’s going to do the research faster. It’s going to organize information better. It’s going to write cleaner, more structured content than most people can on their own.
We’re not going to win by trying to out-AI AI.
But the last mile should still be ours.
The last mile is where you take what AI gives you and make it human. It’s where you apply judgment, context, tone, and experience. It’s where you decide what matters, what doesn’t, and how it should actually land with the person on the other end.
I was reminded of this again recently working with a team where I had built prompts for reps to create outbound sequences. The prompts worked. They produced solid outputs based on the frameworks I teach.
But one rep kept coming back frustrated because he couldn’t get the output of the AI to be perfect.
That’s when I realized I needed to be more clear. It’s not supposed to be perfect. And it shouldn’t be. If the output is perfect, then what’s the point of your role in the process?
AI is not the final answer. It’s the starting point.
The problem right now is that too many people are using AI to skip the thinking. They ask it to do the research, write the message, build the sequence, and then they send it without ever really engaging with it.
That might work in the short term, but it leads to the same problem we’ve always had in sales. Everything starts to sound the same.
I see this especially with younger reps and students. I was talking to a group of Sales students at Bentley recently and told them something that didn’t seem to land at first.
If you walk into an interview today thinking your ability to write a personalized email or make a cold call is your differentiator, you’re already behind.
AI can do those things better and faster than you.
What will separate you is how you use it and what you do after it gives you the answer.
Can you take what it produces and make it better? Can you adjust it based on the situation? Can you add context that only comes from actually understanding the business and the person you’re reaching out to?
That’s the last mile.
It applies to everything we do. Emails, calls, proposals, sequences, presentations. AI can get you 70–80% of the way there, maybe even 90%. But the final 10-20% is where the impact is.
That’s where you earn your value.
So instead of asking, “How do I get AI to do this for me?” start asking, “How do I use AI to get me close so I can make this better?”
Use it to:
* Speed up your research
* Structure your thinking
* Generate a starting point
But don’t outsource your judgment.
Add your perspective. Adjust the tone. Make it sound like you. Make it relevant to the person you’re reaching out to.
Because until computers start buying from each other, there’s always going to be a human on the other end making the decision. And that human is going to feel the difference.
That difference is the last mile.
#MakeitHappen
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