Simon Oster
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When AI Meets Indecision: Strategy Lessons from Hesitant Leadership

AI has moved from hype to habit. With around 88% of companies now using AI, it is no longer a differentiator to experiment. Yet leadership decisions often lag behind.

January 20267 min read

AI Has Moved from Hype to Habit

With around 88% of companies now using AI in at least one business function, it is no longer a differentiator to experiment with AI in 2026. At the same time, the global AI market is projected to grow at close to 33% annually this decade, underscoring how fast the gap can widen between early movers and slow responders.

Yet in many organizations, AI is advancing faster than leadership decisions. Tools appear, pilots emerge, employees experiment—and the executive floor is still debating definitions, risk statements, and ownership.

The Leadership Bottleneck

Corporate history is full of warnings about delayed decisions. Kodak invented digital photography but failed to pivot and and never recovered its leadership in imaging; Nokia dominated mobile phones, missed the smartphone inflection point, and required more than a decade to re-establish itself in networks and AI-driven infrastructure. Yahoo, Blockbuster, and many others failed to adapt and became former versions of themselves.

With AI, the same story risks repeating. While leaders hesitate—waiting for perfect ROI cases, complete governance frameworks, or the "right moment"—AI adoption continues organically at the edges of the organization. Employees plug into copilots, agentic platforms, MCP's, integrate assistants into workflows, and build small automations - a shift now widely described as BYOAI, or Bring Your Own AI. The result:

  • Shadow AI: uncoordinated tools, unmanaged risks, and duplicated effort.
  • Innovation without ownership: promising ideas stall because no one is formally accountable.
  • Strategy lag: technology moves in sprints, leadership in committee cycles.
Indecision becomes a silent architecture—one that shapes how (and how poorly) AI is embedded into the business.

What Effective AI Strategy Looks Like

Across industries, a few common patterns define pragmatic, high-impact AI strategies.

1. Leverage, Don't Reinvent

Most organizations do not need to build foundational models. They win by:

  • Using trusted, pre-built models from major platforms.
  • Combining them with domain-specific data, processes, and expertise.
  • Focusing on concrete use cases: contract review, proposal support, design assist, knowledge search, decision support, and workflow automation.

2. Go Broad, Not Obsessively Deep

The goal is less about one "hero" AI project (unless you're an AI startup) and more about raising the baseline of how work is done:

  • Provide clear guidance, guardrails, and training so everyone can use AI safely.
  • Encourage everyday efficiency—drafting, summarizing, analyzing, researching—across as many teams as possible.
  • Treat AI literacy as a core skill, not a niche capability.

3. Centralize Expertise, Decentralize Innovation

AI works best when there is both freedom and focus:

  • A Center of Excellence (CoE) sets standards, governance, ethics, and architectural patterns.
  • Business teams own use cases, supported by AI champions who bridge strategy, operations, and technology.
  • A single AI platform (not a zoo of disconnected tools), led by your strongest development team, underpins scaling, integration, and security.

4. Turn Governance into an Enabler

Regulation such as the EU AI Act is tightening, and that is a good thing:

  • Robust governance frameworks, risk classification, and transparency measures build trust.
  • Ethical and legal oversight should be built in from the start, not bolted on at the end.
  • Clear roles (system owners, data owners, process owners) reduce ambiguity and accelerate decisions instead of slowing them down.
In short: AI transformation is ultimately an organizational story dressed in technology. Tools change quickly; habits, skills, and culture take longer. Organizations that thrive in an AI-powered era do a few things particularly well: leadership takes ownership, strategy connects business and technology, and cultural readiness turns uncertainty into momentum.

A Strategy Deep Dive Invitation

If this resonates and you feel your organization is somewhere between curious and stuck, that is exactly the zone where a good strategic conversation can unlock real momentum.

We can explore:

  • How to move from scattered pilots to a coherent AI roadmap.
  • How to balance speed, risk, and regulation.
  • How to turn leadership hesitation into decisive, aligned action.
No slide decks required. Just a candid conversation about the future you want to build and the decisions it will take to get there.

Let's continue the conversation

Have thoughts on this article? I'd love to discuss over a coffee.