When we started our Live, Cory Blumenfeld had used AI seconds before joining us to help answer a potential customer.
Joel Salinas had it running in the background, reading a client email and attachment. Philip Hofmacher had already checked in with his AI running coach about his ultramarathon training.
We’d gone live to talk about how much of our work AI should do while all four of us were already handing it jobs that would have taken our time a year or two ago.
What interested me more was how differently we treated those jobs once AI could do them without us. 👇🏻
Start with what you can check
Philip runs much of his business through Notion and now uses AI to build pages and set up automations without learning every click himself. Cory uses it for repetitive jobs throughout his day, documenting conversations, updating his CRM, preparing emails and finding people he’s forgotten to reply to.
Cory is comfortable handing over jobs where he can quickly tell whether they’ve been done properly. Summaries and moving information around are easy to check. Once something needs his judgement, he gets involved.
Joel goes further. When he publishes on Substack, AI can turn the original piece into a LinkedIn post and carousel, then publish them without him seeing them first.
Trust has to be earned
Joel spent months testing the process and adjusting the rules before he was comfortable letting it run alone. He knows the original material well enough to judge the LinkedIn version because he wrote it and spent months testing the process.
On another post, he was short on time and let AI write the introduction. He published it, read it again five minutes later and took the whole post down. The SEO and keywords were fine, but it didn’t sound like him.
That first workflow works because Joel knows the source material well enough to catch when the adaptation goes wrong. Handing over something you don’t understand yourself is much riskier.
Your name is still attached
Philip tried letting AI reply to his Substack messages early on and stopped within a week. Nobody complained. He didn’t like people believing they were having a conversation with him when they weren’t.
Joel draws a line around email and comments. AI reads the background and prepares a Gmail draft. He still checks it before anything goes out.
A bad post or piece of advice can damage trust you spent years building. If an email gets something wrong, the model doesn’t deal with the customer afterwards or explain bad advice to a client. You’re the one dealing with the fallout.
AI changes who you can hire
Hiring another virtual assistant made Philip look at AI from the other side: what could somebody else now handle with AI helping them?
Previously, they’d struggled to give a VA a wider range of jobs because the business had too many moving parts to pick up quickly. With good documentation and the AI tools they’ve built, a new VA can take on more much sooner without knowing every corner of the business first.
It made me ask something else: what happens when AI helps you do something before you’ve learnt enough to judge the result?
The polished answer can still be wrong
If you don’t understand good writing, you’ll struggle to spot a weak draft. The same problem appears when AI communicates with customers or makes decisions for you. A mistake in judgement can now sit underneath perfectly reasonable wording.
Cory disagreed with part of that. Some of his early LinkedIn writing with AI was awful, he said. The important part was that he started writing. He paid more attention to other writers and asked better questions as his own writing improved.
AI can help you try something before you’re particularly good at it, and that can become part of how you learn. The problem comes if you never develop enough judgement to stop accepting whatever it gives you.
That becomes more important as AI starts doing more without you. I’m already giving it jobs I wouldn’t have handed over a year ago, and that list is growing.
Before I stop checking another one, I want to know I’d still catch the bad answer.
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