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Scaling Judgment

Most founders think scaling means better delegation.

"I need to delegate more tasks."

But delegation just moves the work. It doesn't scale the judgment.

Your team can execute what you tell them to do. But they struggle with what you would do in novel situations.

That's where the digital twin concept changes everything.

Instead of just delegating tasks, you systematize how you think.

→ How do you evaluate risk? → What patterns do you recognize? → What trade-offs do you make?

When that thinking becomes embedded in your systems, your team doesn't just execute your decisions. They make decisions the way you would.

Even when you're not there.

That's not delegation. That's scaling judgment.

And that's how you break free from being the bottleneck in your own business.

The Experience Gap

Had coffee with a founder last week who said something that stuck with me:

"We've grown fast, promoted good people, but most of our management team has been in their roles less than two years."

I've seen this scaling challenge many times.

You elevate people from within because they know your culture and processes. But now they're learning leadership while managing complex projects.

Meanwhile, the institutional knowledge sits with one or two people at the top.

→ Every complex decision flows upward → Every non-routine situation needs senior input → The team is capable, but lacks pattern recognition → Growth becomes limited by senior leader capacity

The team is capable, but they haven't developed the judgment that comes from years of seeing patterns, making mistakes, and learning from edge cases.

Growth becomes limited by how much the senior leaders can personally handle.

This isn't a people problem. It's a systems problem.

The expertise exists. It's just trapped in a few heads instead of being systematically transferable.

That's where the real work happens - making invisible wisdom teachable.

It's a hard problem.

The Pre-Solved Problem

A client told me a story that perfectly captures why I do this work.

He needed a specialized legal document for a project close to his heart. Had never drafted one before.

Instead of immediately calling his lawyer, he spent some time with AI. Created detailed prompts. Worked through multiple iterations.

Generated a comprehensive document that covered all the key elements.

Then he sent it to his counsel for review.

They made minimal changes and sent him a four-figure bill.

"That changed how I think about every bottleneck in my business," he said.

→ It wasn't about replacing expertise.

→ It was about doing the heavy lifting first.

→ So expensive knowledge could focus on what really mattered.

→ It redefined how he approached bottlenecks.

Now he's asking: What other patterns in my business could work this way?

Sometimes the most expensive thing you can do is not think differently about how work gets done.

Curious what problems are you pre-solving in your business?

The Founder Bottleneck

Your team is waiting for you to make decisions.

While you're in back-to-back meetings.

You've become the thing that's slowing down your business.

Here's what I see with otherwise great businesses with millions in revenue:

→ Every critical decision flows through the founder → Team has capability but can't execute with founder's intent → Growth is capped at the limit of founder's personal capacity → Founder is trapped in operational weeds

Sound familiar?

This isn't a people problem. It's an architecture problem.

The solution isn't hiring more people. It's building systems that scale your judgment.

What's the biggest decision bottleneck in your business right now?

You'll get: - Your personalized bottleneck score across 3 key dimensions - Specific insights into where you're constraining growth - A customized action plan for scaling your decision-making - Estimated time cost of your current approach

The assessment takes just 5 minutes and provides immediate insights you can act on today.

This Changes Everything

The paradigm shift that's redefining business decisions:

Every tech revolution has that moment when you realize "we can do something that was literally impossible yesterday."

GPS went from printed MapQuest directions to real-time navigation that adapts to traffic, construction, and your driving patterns.

AI's moment? Making someone else's complete reasoning process as visible and navigable as a real-time map.

For the first time in business history, you can see exactly how your team thinks through problems, trace their assumptions, and build on their logic in real-time.

This isn't just about better meetings. It's about:

🔷 Scaling your decision-making quality without scaling your time investment

🔷 Coaching thinking processes, not just outcomes

🔷 Building competitive advantage through collective intelligence

🔷 Eliminating the "black box" of team reasoning

Ben Thompson (Stratechery) experienced this breakthrough: "absolutely blown away." Instead of being a bottleneck for complex decisions, he could now scale his thinking process. His assistant became an extension of his analytical capability rather than just another person who needed oversight.

How to unlock this in your organization (3 steps):

But first: Tech won't solve alignment problems. If your team isn't rallied around shared vision, start there. Do it now! I'll wait :)

Step 1: Make thinking visible, not just conclusions

Step 2: Create shared context before decisions

Step 3: Build on each other's thinking

2025 will separate teams that use AI from teams that think together through AI.

↳ Try step 1 in your next meeting. You're about to discover what was impossible yesterday.

Work ON your business, not IN it

Every business owner wants to work ON their business, not IN it.

But here's the problem: You can't scale yourself if you don't understand how your team thinks.

Right now, your people are using AI individually. Sales uses ChatGPT for proposals. HR uses AI for screening. Finance has their own tools.

You're hearing conclusions, but you can't see their reasoning process.

Deloitte found that 26% of workers are using AI without their manager even knowing. That's not just an adoption gap—it's a leadership blind spot.

Meanwhile, Harvard research shows teams using coordinated AI are 3x more likely to produce top-tier solutions. Not because the AI is better, but because the team thinks better together.

↓ Swipe to see how coordinated AI becomes your window into your team's thinking.

(And why this changes everything about scaling leadership)

Your team's AI use is creating a hidden problem

Your team's AI adoption is creating a hidden problem.

Everyone's individually more productive. AI is everywhere. Each department has their favorite tools.

But somehow, cross-functional decisions feel harder than ever.

Microsoft data shows 75% of workers use AI, but 60% of leaders have no coordination plan.

The result? AI chaos disguised as progress.

↓ Swipe to see the 3 warning signs your team's AI use is fragmenting instead of connecting.

(And what coordinated AI actually looks like)

People are the hard part

"People are the hard part."

That's what a design leader told me the other day when we were discussing AI coordination challenges.

Here's what I see everywhere: → 75% of knowledge workers using AI (Microsoft data) → 60% of leaders have no coordination plan → Result: Teams that can't learn from each other's thinking

This design leader's team was using AI to generate feedback on product docs. Smart approach. But each designer was doing it individually, in isolation.

When product management issues came up in 1-on-1s (a "perennial topic"), everyone used AI to brainstorm solutions. But nobody could see HOW their teammates were thinking through the same problems.

No shared assumptions. No visible reasoning. No way to learn from each other's approach.

Ben Thompson from Stratechery just cracked this: When his assistant shared ChatGPT conversation links instead of just conclusions, Thompson could trace every assumption, see the complete thought process, and build on the work seamlessly.

His reaction: "I was absolutely blown away."

This is the breakthrough: Teams need to understand each other's thought processes, not just share AI outputs.

When teams can see HOW each other thinks with AI, they build shared trust and learn from each other exponentially faster.

Individual AI adoption has a ceiling. But coordinated thinking? That compounds.

Can your team see each other's AI reasoning process, or just the results?

How to use AI like it's your job

Every company on earth is sending out its version of Shopify's "use AI like it's your job" memo right now. Yours may have already.

It brings up all sorts of confusion about where to start. Dabble with ChatGPT or build a world-changing agent?

But there's actually one critical concept that makes adoption way more impactful right away: it's a multiplayer game, not a single-player one.

What does multi-player AI adoption mean?

Years ago, I led a project that seemed on track. We were close to deadline, features looked great... except one. The tech for that piece just wasn't there.

I thought we were okay given the many positives, but the client? They saw it differently. That one problem feature threatened the entire project's value. A classic, costly miscommunication.

Hard won experience helps mitigate miscommunication: deliver value early and often, etc.

But it's still a challenge and who doesn't want access to more clarity?

This is where multi-player AI is amazing. And here's how to make it work for you:

  1. Define Your Core Company Context: This is crucial. Don't guess. Articulate your company's values/mission/purpose. Why do you exist? What are your strengths, weaknesses, and goals?

This isn't just another document; it could be the most important writing you do. It's invaluable on its own, and essential because AI is totally generic until you tell it who you are and what you care about.

  1. Build Your Team's "Clarity Partner": Create a shared NotebookLM project (or Claude, though many already have NotebookLM via Google Workspace; ChatGPT doesn't offer shared projects yet). Upload your core company context.

  2. Empower Your AI Clarity Partner: Treat this shared space as your most insightful advisor and strategic partner. Remember, it gains its power from the team context you provide, the deep thinking you've done to define your team.

  3. Spot Misalignments Early: Feed it your strategic docs, project ideas, meeting notes. Ask your AI Clarity Partner to flag where conversations or decisions might be drifting from your stated values or project goals.

Do this as a team! Within days you will have improved your most important capability: to make high quality decisions together.

I wish it was there to help me spot my team's misalignment so many years ago.

And if you're looking to take action on your company's "use AI!" memo, I'd be happy to talk. Alignment and clarity is great place to start. Feel free to reach out.