For years, goal setting was a whole production.
I'd drive out to the Texas Hill Country, find a cabin for the weekend, and spend two or three days in near-total isolation just to figure out what I wanted to focus on for the next 90 days. No distractions. No calls. Just me, my notebook, and a lot of walks.
It felt necessary. Like the clarity would only come if I physically escaped everything.
That was the old way.
Last December, I ran the same process in under 2 hours. At my desk. And honestly? The output was better.
Here's what changed.
AI Doesn't replace thinking. It Accelerates It.
The big misconception people have about using AI for goal setting is that the AI does the thinking for you. It doesn't. You still have to do the hard work of deciding what matters.
But what AI can do is get you to the hard questions faster.
When I used to go on those cabin retreats, I'd spend the first day just clearing my head. Writing down random thoughts. Dumping everything that had been bouncing around in my brain. Only on day two would I start making sense of it.
With AI, that initial dump-and-clarify phase takes about 20 minutes.
I open a session, share what's been on my mind, and within a few exchanges I'm already at the interesting questions — not still sorting through noise.
The Flip the Script Prompt
Most people use AI the same way they use a search engine. They ask it a question, it answers. That's fine for some things, but for goal setting it's backwards.
When I don't know exactly what I want or how to prioritize competing goals, I flip the script.
Instead of telling the AI what to do, I say something like: “Here's a rough list of goals I'm considering. I want you to help me prioritize them. Ask me what you need to know.”
And then it interviews me.
It asks about my timeline, what matters most this quarter, where I'm already making progress, what keeps getting pushed to the back burner. The questions it asks are often better than the ones I'd think to ask myself.
This works because the bottleneck in goal setting isn't usually information — it's clarity. You already know what's important. You just haven't articulated it yet. The back-and-forth of being interviewed surfaces things you wouldn't have written down on your own.
I've used variations of this with clients in workshops and they consistently say the same thing: “I didn't expect to learn something new about my own goals from that conversation.”
The Question Most People Skip
Here's the prompt I've found most useful in quarterly planning.
It's not “what should I focus on?” Most people ask that. The answers tend to be obvious.
The better question is: “Based on everything you know about me and my current situation, which of these goals should I NOT pursue — and why?”
That one lands differently.
When you ask AI to argue against your goals, it forces the same kind of hard thinking that used to take me three days in a cabin. It brings up the opportunity costs, the conflicts between competing priorities, the goals that only feel urgent because they're exciting right now.
And then you're left with what actually matters.
The subtraction philosophy is something I've come back to repeatedly at Asian Efficiency. It's easy to add more. Taking things off is harder and usually more valuable. This prompt is a fast path to doing exactly that.
How This Fits Into Quarterly Planning
I still believe in quarterly planning. The 12 Week Year approach — picking one meaningful goal and building everything around it — is one of the frameworks we've taught for years. The compressed 90-day cycle creates urgency in a way that annual planning just doesn't.
But the front end of that process, the part where you figure out what the right goal even is, used to be where I got stuck. Too many options. Too much noise. That's where the cabin retreats came in.
Now I use AI to compress that front end. Get clear on what matters, eliminate what doesn't, and show up to the 12-week sprint with confidence that I'm working on the right thing.
The retreat was never about the cabin. It was about having enough uninterrupted time to think clearly. AI gives me that… on demand, in a fraction of the time.
What to Try Before Your Next Planning Session
If you're heading into Q2 planning — or any quarterly review — try this sequence before your next session:
- Write down every goal or project that's been on your mind. Don't filter. Just get it out.
- Share the list with ChatGPT or Claude and say: “Ask me what you need to know to help me prioritize these.”
- Answer its questions honestly. Let it push back.
- Then ask: “Which of these should I NOT pursue right now and why?”
- Take what's left. That's your quarter.
This works whether you're planning your business, your personal goals, or a mix of both.
The cabin was good. But you don't need the cabin.
Want to go deeper on AI-powered goal setting and quarterly planning? I cover this in detail in my Productivity Academy workshops and one-day AI intensives.
