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Hi Friends,
I am in three WhatsApp groups about AI.
They go off at 7am. They go off at 10pm. New agent. New model. New workflow that did not exist last Tuesday. The goal post of AI capability is shifting weekly.
This is the greatest technological shift in my career since maybe the internet, except this one is already in the pockets of billions of people.
ChatGPT alone has 900 million weekly users. Add Gemini, Claude, and Meta AI and you are closer to 3 billion.
AI Adoption is Faster Than the Internet and Cellphones
Image: Winbuzzer, Microsoft
The low barriers to adopt AI over a steam engine or electricity is what fascinates me the impact AI will have in a compressed timeline.
It is the most fun and scariest time of my career to figure out strategy.
Today I want to share the framework I keep coming back to, and the one question I use to test whether a strategy still holds.
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The Framework I keep Coming Back To
Years ago I read Michael Watkins' First 90 Days. The best book ever written on leading through change. The framework he laid out has become my first principles thinking. Every project I take on, big or small, runs through it.
Watkins describes defining strategy as an expedition. Before anyone moves, the team has to answer one question. Are we climbing a foothill or are we climbing Everest? Where are we going and why. That single decision changes everything below it that needs to happen.
Five layers. Each one built on the answer above.
Destination. The summit. Where are we going and why.
Route. The path up the mountain.
Process. How decisions and work flow on the climb.
Systems. The gear. Ropes, oxygen, supply chain.
Team. The climbers on the rope.
A foothill needs a different route, different gear, different team than Everest. Get the summit wrong and every layer below it is wrong too. You can easily see how all 5 need to be aligned for success.
Most teams I see are jumping to AI automation and agents without thinking about the steps before. They pick a destination based on the team they have, what the budget will approve, their last competitors release, or poorly crafted quarterly goal.
Destination is the lead domino. Everything else follows. Always.
How Do You Pick a Moving Mountain?
So here is the harder question. How do you pick the right destination when the mountain itself keeps moving in the world of AI?
First, you must compress the timeline. 5 year destinations must be compressed to 18 months. Any longer you are kidding yourself.
Also, I believe conviction of the destination itself maybe the greatest moat right now in this AI world.
The test for a destination has always been the same. Are we generating unique value over alternatives? Are we solving a pain point better than alternatives? Alternatives used to mean competitors, the status quo, a spreadsheet, hiring an intern.
In 2026, that alternative list added a new player. A $20 a month frontier model your customer is already paying for. That is the bar your destination has to clear now.
If your customer can open ChatGPT tomorrow morning and get something acceptable, your destination is on borrowed ground.
What Happened to Chegg
Chegg is the textbook case. For over a decade, they were the dominant homework help platform. Students paid monthly to access a database of textbook answers, study guides, and tutoring. Three million paying subscribers at their peak. Valuation, $15.3 billion dollars in Feb 2021.
Then ChatGPT launched. Students realized they could get the same answers for free, faster, with no subscription. Traffic collapsed. They sued Google over AI Overviews. Last October they cut nearly 50% of staff. The CEO blamed the new realities of AI. The stock trades near a dollar today.
Chegg picked a destination AI broke. The mountain moved. Their destination did not.
The One Question
Ask this Monday morning before anything else hits your calendar.
If a customer asked their ChataGPT to do what we do tomorrow morning, what part of our value would survive, and would they still pay us for it?
Write down what survives. One sentence.
Now read it back. Would your best customer actually pay for that? Would they pay more for it than for the AI alternative? Would they pay enough to keep your business profitable?
If yes, you have a destination worth defending. Spend the next quarter making it impossible to copy.
If no, that is your work. Move the mountain.
As AI gets cheaper, the work AI cannot do gets more valuable.
Your destination should sit there.
Til next time,
—Ali
About Me: AI-powered go-to-market strategist. I meet B2B leaders where they are at and use AI without losing what makes them worth paying for. Follow me on LinkedIn
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