Why Companies Make Bad Decisions

Why Trust Matters in Executive Decision-Making

William shares a story from an enterprise sales meeting that became the inspiration for The Room Goes Quiet.

His team had presented what they believed was the best solution. But the CIO was worried that the project could become a political battle and ultimately fail.

Instead of trying to convince her that everything would be fine, William acknowledged the risks and explained three problems he expected them to encounter.

That changed the conversation.

He wasn’t simply selling a technical solution. He was demonstrating that he understood what the CIO was facing and could be trusted to stand beside her when problems occurred.

As William explains:

“I can have the best solution in the world, but if I can’t convince the person across the table that I’m going to be there with them…they’re going to buy a solution that’s worse than mine.”

For anyone selling complex B2B or enterprise solutions, that’s an important distinction: buyers aren’t evaluating the product alone. They’re also evaluating the risk of choosing you.

Why Consensus Doesn’t Always Lead to Action

Why do projects everyone supported in the meeting sometimes disappear afterward?

William points to organizational momentum, overloaded teams and lack of accountability.

Changing this requires leaders who are willing to name uncomfortable problems—and people around them who are willing to challenge their thinking.

William recommends deliberately having a contrarian in the room: someone willing to ask about the elephant everyone else would prefer to ignore.

But inviting disagreement isn’t enough. Leaders also have to listen.

As William puts it:

“You can be successful without strict accountability. You can’t compound success without that level of accountability.”

How Do Leaders Build Trust?

One of William’s simplest leadership principles comes from his father:

“Say what you mean, do what you say.”

He also suggests evaluating managers differently. Instead of asking only what that manager personally achieved, look at what happened to the people around them.

Did they help people develop? Did people on their team advance? Did they make others better?

William argues that leadership ultimately shows up in how effectively someone raises the performance of those around them.

The same principle applies to enterprise customers. Trust isn’t created simply by taking a client to dinner or asking about their family. Genuine curiosity about the customer’s business, goals and success can create a much deeper relationship.

Is AI Making Human Judgment More Valuable?

The conversation then turns to one of the biggest questions facing business leaders: What happens to decision-making as AI becomes embedded in organizations?

William doesn’t believe we’re simply entering an AI revolution. He describes something potentially more important:

A judgment revolution.

AI is rapidly commoditizing knowledge. It can analyze information and produce answers that look remarkably authoritative.

But an answer that looks authoritative can still be wrong.

That makes human judgment increasingly important.

Executives need to know when to question AI-generated information, verify assumptions and determine who ultimately owns the decision.

This is already affecting enterprise sales. William describes showing a sales team how a potential customer could ask AI what their solution should cost—and receive a confident answer roughly one-third of the actual price.

Suddenly, the seller isn’t simply explaining value. They’re dealing with a buyer who may arrive at the conversation armed with inaccurate information that appears credible.

Key Takeaways

Trust can outweigh having the technically superior solution. Enterprise buyers need confidence that you will be a reliable partner when things go wrong.

Accountability turns consensus into action. Someone ultimately needs to own the decision and its consequences.

AI makes judgment more—not less—important. As knowledge becomes easier to generate, the ability to question, validate and interpret that knowledge becomes increasingly valuable.