How to See Around Corners (Before It’s Too Late)

Executive Debt doesn’t just come from bad decisions—it comes from blind ones.

Most leadership mistakes aren’t the result of incompetence. They happen when leaders fail to anticipate the ripple effects of their choices. This week’s post is about building better decision-making habits, so you can foresee consequences, model scenarios, and reduce your future debt burden.

1. The Fog of Leadership: Why Decisions Go Sideways

In the moment, decisions often feel clear. But hindsight is 20/20—and executive decisions rarely play out exactly as planned.

Why? Because we’re human. And our judgment is clouded by bias, urgency, pressure, and partial information. The result is a decision that feels rational in the moment but creates chaos later.

What to Watch For:

• Assumptions that go unchallenged
• Pressure to decide without consultation
• Overconfidence in best-case scenarios

Fix it: Use decision premortems. Ask, “What would have to go wrong for this to fail?”

2. Strategic Anxiety: The Right Kind of Worry

Strategic Anxiety is a powerful tool—it’s the practice of asking “What if…?”

“What if this market shifts faster than we expect?” “What if our talent strategy fails to scale?” “What if our decision alienates a key stakeholder?”

This mindset isn’t fear-based. It’s foresight-based. It prompts scenario modeling and risk-mitigation planning.

What to Watch For:

• One-dimensional planning
• Groupthink in strategy sessions
• Leaders rewarding certainty over curiosity

Fix it: Make “What if?” a core leadership habit. Use red-teaming and scenario planning.

3. The OODA Loop: A Framework for Adaptive Decisions

Originally developed for fighter pilots, the OODA Loop (Observe, Orient, Decide, Act) is now used in everything from military tactics to business strategy.

Here’s how it helps avoid Executive Debt:

• Observe: Gather data, trends, frontline insights.
• Orient: Understand internal context and biases.
• Decide: Choose based on options, not impulses.
• Act: Execute decisively—then loop back.

Fix it: Build this into executive discussions. Especially during high-stakes decision cycles.

4. AI-Assisted Foresight: Humans + Machines

Today’s leaders have a secret weapon against Executive Debt: AI.

Predictive analytics, modeling tools, and LLM-powered assistants help leaders:

• Forecast consequences
• Identify risks
• Simulate market shifts

But AI only works when it complements—not replaces—human judgment.

Fix it: Use AI to model decisions. But keep values, ethics, and intuition in the loop.

Why This Matters:

Better decisions aren’t about being perfect—they’re about being prepared. At AspireSix, we help leadership teams upgrade their decision-making frameworks to reduce rework, rebuild alignment, and move with greater confidence.

Because decisions made in the fog are expensive. But decisions made with clarity can change everything.

Facing a high-stakes decision? Let’s simulate the scenarios together with AspireSix.