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AI Enablement

How to Use AI for Deep Work and Focused Thinking

Rob Cressy
TL;DR
  • Learning how to use AI for deep work and focused thinking starts with protecting time on your calendar.
  • Most people never set up custom instructions. In a room of 200 leaders, about two have done it.
  • The highest output week of my career came from wiping my calendar and using AI six hours a day for a week.
  • Low leverage work can run overnight while you sleep, which gives you back the hours you wanted for family.
  • Clarity beats intensity. Uncertainty leads to inaction, so map your high, medium, and low leverage work first.

If you are a leader who keeps hearing that AI will give you back your time, and your calendar looks exactly the same as it did a year ago, the question you actually want answered is how to use AI for deep work and focused thinking rather than how to use one more app. The gap usually sits somewhere else. Somebody has to protect the hours and set up the context that makes the thinking possible.

I learned this the expensive way. About a year ago I was using AI an hour or two a day and feeling good about it. Then I sat with a thought that would not leave me alone. There is somebody out there right now using AI twelve hours a day, and they are going to run circles around me. So I wiped my calendar for a week and used AI six hours a day, every day. That was the most prolific output of my entire career. Nothing about the tools changed. The container changed.

Why Does AI Feel Like a Tech Problem Instead of a Thinking Problem?

I do not have an AI background. I do not have a tech background. I do not have a coding background. I started at zero the same as everyone reading this.

That matters because most leaders hear the word AI and file it under technology, which means they file it under somebody else's job. The work that actually moves you is building the confidence to lead it yourself. A senior leader I coach at a global manufacturing company said it out loud on a call recently. They told me they were not a systems person and did not know what thinking in systems even meant.

Then they went and did it anyway. They had a business challenge and a team that needed to solve it. Their instinct was to walk in and direct the whole thing, step one, step two, step three. Instead they described the challenge to their AI assistant and asked how to build a system where the right people solved it together. What came back was a collaborative structure, specific people paired with specific people on specific pieces. They told me it was wild, because everyone ended up building the solution rather than receiving it.

That is a thinking win wearing a technology costume. The tool did what they asked once they asked a better question.

What Are Custom Instructions and Why Do They Matter So Much?

Here is the single highest leverage setup step, and almost nobody does it.

When I give a keynote, I take a version of my foundational method and run it from stage. I always ask the same question by show of hands. How many of you have set up your custom instructions and your personalization? In a room of 200 people, I am lucky if two hands go up.

Custom instructions tell the model who you are. They govern your identity, what matters to you, and what you are working toward, and they carry across every model you run. That single change moves AI from a generic version to a version dialed in for you, and it compounds every day after, because the more you use it the more context it holds.

The same leader hit this light bulb themselves. They came in expecting a technology exercise and found themselves writing about their own character and what they were actually about. They described it as having to think deep into their soul about how they wanted to train the thing. They were right. That is the work.

One practical note that comes up constantly. If your organization resets the model back to default every session, you cannot force it to stay on a deeper reasoning mode. You can get most of the way there anyway. Ask your AI directly what you should add to your custom instructions to reproduce that deeper, more structured thinking, then tell it the shape you want back. Mindsets, action items, systems, quick wins. Have it write that concisely enough to paste into your instructions.

How to Use AI for Deep Work and Focused Thinking When You Have No Free Time

Every leader I work with says the same thing. The week is already full.

So start where the week is leaking. I share a prompt with clients I call an efficiency map. It interviews you about your work, then sorts what you do into high, medium, and low leverage. It gives you quick wins you can take today, smarter builds worth setting up, and the one big move. Then it ends with a first win game plan.

Why does it end there? Because one of the quotes I live by is that uncertainty leads to inaction. If you do not know what to do, you are not likely to do anything at all. Simplicity is what people ask for, and clarity is how you get simplicity. Here are the three things, go.

The leader I mentioned wanted more balance. They were running sixty hour weeks and wanted to move ten of those hours toward family. The week after we talked, they needed an infographic built with a colleague. They got into their AI assistant, worked out what they actually wanted to say, and they were done in thirty minutes. Then they went to the beach with their spouse.

That is the whole game in one small story. They did not find more hours. They compressed a task and spent the difference on the thing they said mattered.

Can AI Actually Do Real Work While You Sleep?

Yes, and this is where most people stop short.

Once you are a few months into this you start asking a different question. Why is my AI not running while I am not there? We know it can. So what does it need?

It needs the same four things you would give a new hire. Context, a clear outcome, a definition of done, and a system to follow. This is the whole idea behind digital labor that does work for you while you are somewhere else. That is business 101. You would never hire someone and say go do your thing. You would tell them how things work here.

I call the practice overnight time. Before you close the laptop or leave the office, you pick the thing you are willing to let run for eight hours while you sleep. It does not have to be your highest leverage task. Start with the lowest. You wake up and the work is sitting there waiting for you.

There is an old line from Warren Buffett about wanting to make money while he sleeps. This is the same idea applied to your own output. Do it once and you will not go back.

What Changes When You Learn How to Use AI for Deep Work and Focused Thinking?

Your default question changes, and that is the real shift.

A new project lands on your desk. Before, you would map out how to do it and then wonder where AI might help around the edges. After, you ask a different question first. What is the AI-first positioning here?

You are still designing the full workflow with AI in the frame, then finding the two or three steps that genuinely need you. Steps two, three, and four need a human. The rest can move. You just took eighty percent of the work off your plate because you asked the question in a different order.

I block every Friday. No calls, no clients, no meetings. Some Fridays I go shoot video at the beach for three hours. Some Fridays I sit and build for four or eight hours straight. The point is that the time exists on the calendar before I know what I will use it for.

The other half of this is capture. Everything I learn in those blocks lands in a second brain I can search later, which is what makes the hours compound instead of evaporate. Most people never give themselves the time and depth to create anything. Our capacity is only limited to the size of our thinking, and thinking needs room.

Do You Need Your Whole Team to Do This First?

No, and getting this backwards costs organizations years.

Inside a company, success rises or falls to the level of leadership. This is a top-down move, not a bottom-up one. The biggest hole in the boat is when the leadership team is not using AI themselves, because it is very hard for the people below them to build a practice their leader does not have.

That is also the honest answer to why getting your team to actually use it stalls so often. That is also where the advantage sits. There are a lot of people making very good money right now who have quietly decided they are fine and do not need to do anything with AI. That iceberg moves slowly. Every leader who starts now is buying distance.

One more thing worth watching. A team member of that same leader was building an org chart and adding agents to it alongside people. The instinct after that is usually to ask for more headcount. The better question comes first. Before you hire, look at what agents could take off your existing team so the people you already have move up to higher impact work. You may still hire. You will hire for something different.


How to Start This Week

  1. Set up your custom instructions today. Tell your AI who you are, what matters to you, and what you are working toward. This is thirty minutes that changes every session after it.
  2. Run an efficiency map on your own week. Sort your work into high, medium, and low leverage, and pull out one quick win.
  3. Take that quick win and do it. One thing. Stack ones over zeros.
  4. Pick one low leverage task and give it context, a clear outcome, a definition of done, and a system. Let it run overnight.
  5. Block one recurring window on your calendar for creating. Protect it the way you would protect a client meeting.
  6. On your next new project, ask what the AI-first positioning is before you plan anything else.

The Real Shift

The leaders who get somewhere with this are the ones who decided the thinking was worth protecting time for, then built the systems that let the work continue when they walked away.

Once you see it, you cannot unsee it. You are not going to wake up one morning and decide to stop working in systems. And the glimpse you get in your first week is the smallest version of this you will ever experience. Now imagine your team operating this way. Then the whole organization.

Our capacity is only limited to the size of our thinking. Go make the container bigger.

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Rob Cressy
Rob Cressy
AI Enablement Coach helping entrepreneurs and leaders go from AI curious to AI dangerous. 1,000+ days of daily AI usage. Host of The Undeniable Leader podcast.