I got substantially this same message twice in the last couple of days. They weren't from clients, but rather people who drop a question at my feet because apparently I seem approachable and nice.

One guy wanted to know which LinkedIn automation would make the best outbound LinkedIn message to set up sales meetings. The the other guy was wondering what was the best way to send an AI-powered email sequence to the target accounts.

I love AI - I use it every day. It’s cool & clever. It helps me do things that I COULD NEVER DO ON MY OWN. But here are the things that AI should never do:

I hate to sound like a cardigan with elbow patches wearing guy who yells "Get off of my lawn" to the neighborhood kids, but I'm going to sound a little crotchety here…

The amazing speed and faux professionalism of AI has made some people really fucking lazy. Even worse yet is that the amazing speed and faux professionalism of AI has made some people believe that they can't do things as well as AI can.

AI can do a bunch of stuff better than I can - for instance, I decided I wanted to switch mobile phone carriers, so I had AI go scrub all the carrier sites and figure out which one had the best deal for me and which one had the best network in the places that I go. It did a more complete job than I ever would have. it also put the results in a nifty little interactive doodad that I could share with my wife. I probably could have done the same level of research, but I could not have made an interactive doodad with anywhere near the panache of my buddy Claude Cowork (BTW, want a free week of Claude - here you go!).

To be fair, I had to give Claude a bunch of context around our current mobile phone plan, our actual usage patterns, and our desired outcomes. I set the rules and defined the universe in which Claude went to work…

Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. Not rough transcription you have to clean up. Actual polished text — ready for email, Slack, or any app.

Speak the way you think. Go on tangents. Change your mind mid-sentence. Flow strips the filler, fixes the grammar, and gives you text that reads like you spent five minutes writing it.

89% of messages sent with zero edits. Millions of professionals use Flow daily, including teams at OpenAI, Vercel, and Clay. Works on Mac, Windows, and iPhone.

Start flowing free

But my dear desperate question askers from the beginning of this newsletter wasn't really willing to do the "executive" part. They are enamored of speed and ease.

Here’s the straight skinny, my friends, it's not supposed to be easy. I don't mean that you've got to earn your stripes, and “back in my day we walked uphill both ways to school”. I mean it in the "you've got to put effort in to create something you are proud of" way of thinking. Or, similarly, there is a chemical reaction that causes business growth, and effort is the catalyst.

All business systems and automations are dormant and useless without the catalyst of effort to activate them. The effort might be doing research into 25 companies to find the four contacts at each company that make sense to connect with. The effort might be reviewing all of the news events and messaging of one of those 25 companies to understand where there is a fit between your opportunity and their need. The effort might be sending well-researched and thoughtful emails ten times to each person that you want to create a relationship with.

Get revenue agents, workflows, and automations across every stage of your motion. Access customer data in real time through Attio's web app, MCP, API, and SDK.

Then Ask Attio anything about your business and get instant answers.

It's the CRM that runs the work behind every win.

Try Attio Now

There is a popular programming/coding/AI configuration perspective around defining an outcome and giving AI the resources it needs to accomplish the outcome & let it iterate again and again and again and again until the desired result happens.

But before you can do that, you have to understand the context in which the AI brain is working. You are the one who has to define the desired outcome & you need to determine what resources are needed and can be provided.

You know what this sounds like? MANAGEMENT.

First - I know Jocko Willink, author of Extreme Ownership, is a Navy SEAL, not an Army guy. But nobody plays “Navy SEAL “when they are six years old. They play Army guys. Second, this goes if you are leading a SEAL Squad, an agency team, or a team of agents…there is a hierarchy of intentions and actions that creates great outcomes. (And I had AI make this diagram…)

Each level of this cascade really demands every level be clear about the intention and expectations of the one above. Before you define your mission, which is the collection of activities you are going to put together, execute, and measure. You have to understand what the intention and the desired outcomes are - the Commander’s intent - that the mission is part of.

The team outcomes can only be designed when you know the extent of the mission, and every team outcome plays a specific part in creating a successful mission.

And the individual actions can only be decided upon when the individual knows what team they are on, what that team's mission is, and what the resources, tasks, instructions, and abilities of that team are.

I’m going to sound a little bit like a broken record here, but all of this stuff requires a deep understanding of somebody else's context. (See my many rantings on Return on Understanding - AIC 168 - Are You A Jack (or Jill) of All Trades?, AIC 163 - Does Your Agency Milkshake Bring Brands To The Yard?… heck, if I keep on doing this, we'll be here all day - here is the ROU Archive.

Apollo is the AI revenue engine for teams that are done leaving pipeline on the table. 230M+ verified contacts, automated outreach, and AI that does the busywork for you.

More pipeline, less chaos. All in Apollo.

Sign up for free

They focused solely on the individual tasks that AI could do. They wanted the thing that would accomplish their commander’s intent, their mission & their team goals without ever truly defining what they are.

AI is a tool. It feels pretty magical and can do amazing things, but you need to treat it like an electric toothbrush…if you just turn it on, it's going to bounce all around your sink and never clean your teeth, because it's just doing what you have asked it to do. When you clicked the ON button, it thought, "OMG, they want me to vibrate now!" So it did.

You never told it to get the toothpaste, put itself in your hand, and then place the bristles in your mouth, then turn on. There is no way it could accomplish the commander's intent of clean teeth and sparkly, fresh breath, because it is at the bottom of the cascade of understanding.

Until you determine the commander's intent, the mission, and the team goals, quite frankly, your AI isn't a whole lot more useful than a toothbrush that's not in your mouth.

So do the hard work of determining intent and mission and responsibilities, because that's your job. And maybe read Extreme Ownership…

You might have the dreaded agency disease of WAH-WAH. This it is a 100% preventable affliction that makes you sound like adults and teachers in Charlie Brown.

This disease impacts about a hundred thousand agencies every year. They are so afraid to scare away business that they start to say things that are so wishy-washy they become indecipherable. WAH-WAH disease makes it impossible to attract new clients.

Luckily, there is a cure. It’s called DemandOS. It’s an intensive positioning and demand generation protocol that has a 100% Wah-Wah disease cure rate.

But Tim, How Do I Know If I Have Wah-Wah Disease!?!? I’m frightened!

we understand, and we've worked with the best scientists in the land to create a foolproof diagnostic test.

This test is 100% free, takes under 5 minutes, and in thousands of tests, has never been wrong.protect yourself from a progressive case of wah-wah disease and get your free Wah-Wah Detector test today! Don’t delay!

Our sponsorships are ads (obviously). But some of the companies or services linked in our content may pay us a minimal commission if you buy something from them. Potential payment is never a factor in what we link to, and we have direct experience with every company or service we mention in our content.