Why Your AI Strategy Has a Human-Shaped Hole (And How to Fill It)

Bridging the gap between AI capabilities and organizational knowledge

"I feel like I'm updating products that no one understands because they were built by people who no longer exist and the reasons weren't shared with anyone remaining." A coaching client shared this observation, raising a challenge many PMs face today.

Does that sound familiar?

Welcome to the intersection of Conway's Law and the AI revolution. When your software mirrors your org chart, it becomes a living museum of "organizational archaeology," reflecting every decision, pivot, and compromise. Layers of code, processes, and forgotten choices pile up, creating products and user experiences so complex that even superintelligence won't be able to navigate them.

Here's what this looks like:

• A simple feature change requires consulting three teams.
• Documentation exists, but it does not match reality.
• 'Quick fixes' take weeks because no one understands the full impact.
• New team members spend months learning how things are interconnected.

AI can analyze code and documentation, but it cannot understand the unwritten context behind decisions, such as cultural factors or trade-offs made during Slack discussions and multi-stakeholder meetings. Meaning, AI cannot navigate the “dragons.” Humans can unravel and fix complicated work systems which AI cannot.

Today we’ll explore why your team’s humanity (ability to read between the lines, connect disparate dots of organizational lore, and bridge old and new approaches) might be your strongest competitive advantage in an AI-powered world.

Let's tackle some dragons and explore how to turn organizational chaos into clarity.

Why Traditional Leadership Approaches Are Failing

Every company, including startups, has tech debt. There are decisions the team considered and pushed aside. Features introduced to convince must-have customer(s) to sign. Ignored user research because Steve Jobs said ‘People don’t know what they want until you show it to them.’

The real challenge isn't the tech debt itself, but how we respond to it. I've seen three common patterns at Pearson, SimplePractice, and the Chan Zuckerberg Initiative:

1. Clean Slate Myth: Teams attempt complete rewrites, only to recreate the same complexity in various ways.
2. Process Pile-on: Adding more processes to manage complexity, making things more complex.
3. Documentation Delusion: Believing that if we document everything and wait for the perfect answer, the complexity will be easier to handle.

At SimplePractice, a seemingly simple change caused issues across the platform. While leaders asked us to add more documentation and controls, this created further delays and stress. Instead of encouraging flexibility, control backfired.

The components, integrations, processes, and team dynamics carry forward. In Conway’s Law speak, you end up with “here be dragons.” The warning is innovation and change must tackle not just the technology, but the ways humans collaborate and communicate.

Instead of fighting complexity, let’s help our teams adapt, embrace flexibility, and befriend the dragon. Not a leader? The Adaptation Advantage quotes Brené Brown:

“A leader is anyone who takes the responsibility to find the potential in people and processes and has the courage to develop that potential.”

One Thing AI Can't Imitate

While AI excels at finding patterns in existing data, it struggles with true creativity. AI can blend artistic styles or predict a trend will recur, but it cannot create entirely new ones from scratch.

“AI can be at the center of a product, a strategy, or even a company’s DNA, but it cannot be at the center of a sustainable competitive advantage. Testing AI against the three defining aspects of a sustainable advantage reveals why: To be sustainable, an advantage must be valuable, unique to an organization, and inimitable by other businesses…. AI is unquestionably valuable, but it fails the other two tests because it is neither unique to any organization nor inimitable.”

Your team possesses what Robert Root-Bernstein calls in Sparks of Genius: The 13 Thinking Tools of the World's Most Creative People, the ability to…

See novel possibilities, forge unexpected connections, and make leaps of logic.

These uniquely human capabilities emerge in psychologically safe environments. When people feel overwhelmed and uncertain about their value, they shut down the creativity that makes them irreplaceable. They default to following processes and avoiding risk instead of innovating.

People are not just nice to have, they are your competitive strategy. This is especially true when humans prefer to stay at your company versus join a competitor offering a bigger paycheck and questionable ethics.

For example, despite not matching Meta's salaries, Anthropic has retained talent. CEO Dario Amodei emphasizes their strength lies in something money cannot buy: "alignment with the mission."

Their mission to develop AI with a strong emphasis on safety and using technology for good has created a unique culture that attracts and retains top talent.

New research from venture firm SignalFire shows that [Anthropic] is increasing its engineering organization faster than those competitors and more. The $170 billion AI company is hiring engineers 2.68 times faster than it’s losing them. That number is 2.18 for OpenAI, 2.07 for Meta and 1.17 for Google.

Choosing Your Operating System

Don’t have the Anthropic brand backing you? There are other ways to navigate today’s challenges.

Lean into Emotional Intelligence

I recently received my EQ-i 3.0 and EQ 360 (emotional intelligence assessment) certification. To continue building on the learning, I read Seven and Half Lessons About the Brain by Lisa Feldman Barrett.

Did you work where leaders lashed out? Over time, you’ll hesitate before putting forward a recommendation. Did you share ideas with a leader or peer who claimed them as your own? Trusting other colleagues won’t be easy. Why? Barrett explains our brains predict experiences and actions based on past information.

To reset your brain, change the dynamic. Our brains are interconnected. When we’re stressed, others pick it up and our reality is reinforced. For example, a client had little luck obtaining buy-in for ideas despite their value.

I recommended conducting experiments.

1. Instead of going it alone, leverage the Ikea effect and partner with a colleague in another department on a project that impacts both teams. The colleague championed the idea with their team, bringing more interest to my client’s idea.
2. Practice pitches to execs with individuals who have been successful before. Learn to frame points, anticipate questions, and identify where the exec looks for verification. The discussion led to multiple leaders supporting the idea.
3. Let customers (internal, external) do the talking. My client previously thought the idea’s value was sufficient. Having internal customers showcase its value like time saved, and teams across the business asked to test the idea, increased its velocity and reach.

Let Optimism Be Your Guide

I wrote about “Let Them” by Mel Robbins. I started listening to her podcasts. I appreciate her optimism despite admitted faults. She doesn’t gloss over the hard stuff or make me use AI to decipher the words, she calls it as it is.

In today's AI era where jobs may be replaced and complexity is the norm, choosing optimism becomes a leadership superpower. I'm not talking about toxic positivity or ignoring problems. I'm talking about "responsible optimism," encouraging your team's ability to respond creatively to complexity while acknowledging reality.

You can bring these factors to your organization and create an environment where creativity (and human brains) flourish amidst constant change. For inspiration, I return to leadership insights from Microsoft’s Satya Nadella and a few of my own.

• Encourage team members to clarify ambiguous situations instead of letting unknowns slow them down.
• Amp up team effectiveness over individual achievement by promoting cross-team collaboration to solve complex problems.
• Acknowledge that everyone, including you, is learning. Share your thinking process openly, even when uncertain.
• Create opportunities to explore new tech and resulting complexity. I mentioned holding an “hour of learning” previously.

Normalizing uncertainty and modeling optimism helps your team's brains rewire for resilience instead of stress. Your mood becomes your team's mood and influences your company's culture over time.

One Step to Take This Week

Don't leave navigating complexity to execs. Success comes from consistent, small (optimistic) actions that build adaptive capacity over time.

This week's practice: Start one team conversation with this question: "What's one thing we're learning about navigating [current challenge] that we didn't know before?"

This straightforward question does three things:

1. Acknowledges ongoing learning (good for stressed brains)
2. Highlights progress through complexity (builds confidence)
3. Frames challenges as learning opportunities (fosters growth mindset)

If you do this consistently, your team will start seeing complexity as something they can manage, not something that manages them.

Connecting It All

Complexity isn't going away, and the pace of change isn't slowing down.

Remember the product manager who faced updating products "built by people who no longer exist"? Their challenge reflects a broader truth: While AI promises to solve our problems, our real competitive advantage lies in how we help our teams navigate complexity with creativity, optimism, and purpose.

Modeling optimistic resilience and fostering human creativity isn't just managing complexity. You're building adaptive skills that turn uncertainty from a threat into an advantage.

The question isn't whether we can control the chaos. The question is: How will you help your team train the dragon within it?