Can AI Make Strategic Decisions For You?

Using AI as a shortcut for thinking comes at a cost.

“To most people nothing is more troublesome than the effort of thinking.” – James Bryce

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As you may know, I’ve been working on evolving the direction of this newsletter. One of my goals is to create a clear content strategy that aligns with the problems I’m curious about and those I help my clients with. Naturally, I was curious to see if Claude or ChatGPT could help me.

So I did what you would probably do, too: I gave AI everything I could to help it understand what I was working on, what topics I was wrestling with, and my point of view. My hope was that if I just gave it enough information, a thoughtful enough prompt, and told it which expert advice to follow, it could create an effective content strategy for me.

On the surface, the result was impressive: I had a fully fleshed out plan, chock full of content pillars, topics, and even a calendar. It checked all the boxes for what a solid content strategy should look like.

But there was just one issue.

Where my process broke down

Every time I read through the AI-generated content strategy, it felt foreign. It was like I was reading a good example of what a good content strategy might look like in theory, but not one that felt like my content strategy. It seemed vestigial, like something that had been appended to my thinking but not integrated into it.

Turns out, I had skipped the important part.

I had failed to spend time discerning. I didn’t contemplate questions like: What am I best equipped to write about? What do I feel compelled to share with my readers? What do my clients need to hear about that others aren’t speaking about? And most importantly, who do I need to become to write about these ideas effectively and convincingly?

In other words, I had the answers but none of the meaning behind them.

In the end, put away Claude and ChatGPT and sat down to think. It’s hard. And it’s kind of a pain. But that’s the point. Because now that I’ve had a chance to think through these ideas myself, I feel much more convinced about where I’m headed. And whatever I end up with, I’m more likely to stick with it, because I will have internalized the why behind the answers.

I’m coming to realize, as I bet you are too, that while you can outsource strategic decision-making to AI, doing so comes with a tradeoff. You might get an answer faster, but skipping the discernment process means you may abandon that answer just as quickly. Or you may fail to move forward at all. When it’s not your answer, you have no skin in the game. You haven’t internalized the why. If you don’t like the ramifications of that AI-generated decision, then AI can just as easily give you a different, more palatable answer.

Won’t this improve as AI gets better, though?

Consider this story.

Humans must discern before making big leaps

It comes from the book of Exodus. It begins with Moses, living outside of Egypt, tending sheep in the wilderness. One day, God speaks to him, appearing as a burning bush. His direction is clear: he wants Moses to confront the Pharaoh and lead the Israelites out of slavery and out of Egypt.

But Moses struggles with what’s being asked of him. So he protests. Not just once, but over and over again. I’m not cut out for the task, he says. I don’t know what to say. No one will believe me. I’m not very good with words. Please send someone else.

In the end, Moses fulfills the task God asks of him, but he sure does wrestle with it first. Despite receiving direct and explicit instructions from God, Moses still has to go through a period of discernment before he can move forward. If humans need to discern instructions when they come from the Almighty, why would we be able to skip that process when getting directions from a computer?

You might be wrestling with a big decision yourself right now.

It could be a change in strategy. A new hire. A “lightning strike” event that will show the world what your brand stands for. AI can be great at helping you brainstorm ideas or learn what others have done. But remember this: Your ability to move forward on a bold decision is limited by your belief in that decision. AI can provide you with answers, but it can’t provide you with belief. Belief can only come from within. And belief only happens (and sticks) through discernment.

3 questions I’ll leave you with

1. What’s a major decision you’re facing right now? Have you given yourself enough time and energy to build belief in the right decision, or are you simply looking for a quick answer?

2. Do you have someone who can help you process your thinking? Someone you trust, who can ask you challenging and uncomfortable questions? If not, find one.

3. What’s the environment you need for proper discernment? Are you giving yourself access to that environment, or trying to make tough decisions amidst the noise of the day-to-day?

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Thanks for reading

If we haven’t met, I own a consultancy called Flag & Frontier, where I help my clients define their category strategy, align their executive teams around their strategic narrative, and win their category.

Find out more about working with me by scheduling a 30-minute intro call.

You can also say hello on LinkedIn 👋.

Cheers,

John

P.S. I have some changes coming soon to The Narrative Field Guide. You can read about them here. Can’t wait to share what’s next with you.