The Trust Every Executive Is Expected To Know (But No One Tells You)

“I was not prepared for this.”

If you’re new to a senior role and it’s not what you anticipated, welcome to the club, because executive leadership isn’t all it’s cracked up to be. For years, research has confirmed what executives already know: they aren’t prepared for their new roles.

Studies tell us that 50–70% of new executives fail within the first 18 months on the job. Two-thirds say they did not have a complete picture of what they would be facing, and 75% of new executives say they were not adequately prepared for their roles.

It’s hard to imagine any leader tolerating outcomes like these, yet executive education remains a booming business. I should know. The majority of my clients have attended prestigious Ivy League programs or internally sponsored training programs designed for high-potential leaders. They’ve taken the courses, received coaching, read the books, and listened to mentors.

Einstein said, “Insanity is doing the same thing over and over and expecting different results.”

While executive education can be valuable, we’re missing something if year after year leaders continue to feel unprepared when they take on big jobs. One reason is this: the world has changed dramatically, but the executive playbook hasn’t kept pace. Leaders attend courses and programs, but they don’t go far enough to address the complexity, challenges, and realities of senior leadership today.

For example, trust is one of the most discussed topics in leadership. But as leaders move into enterprise executive roles, many discover that what they’ve been taught about trust isn’t sufficient. After working with executives and teams for over twenty years, I’ve seen that there is a different standard for trust at this level that few leaders are ever explicitly taught, yet they’re expected to just know. I call it Enterprise Trust.
Defining Enterprise Trust

At its most basic level, enterprise trust is how others recognize: “This leader understands what matters to us.”

It shows up when others, including your board, investors, C-suite peers, and employees, experience that your decisions, priorities, and behaviors align with what actually matters at the enterprise level.

Enterprise Trust Isn’t What They Teach in Executive School

Most leadership development prepares people to lead teams, run functions, or manage business units, but you’ll be hard-pressed to find Enterprise Trust in the curriculum. One reason: by the time leaders reach senior roles, there’s an unspoken expectation that they should already know how to operate at this level, even though decisions, tradeoffs, and stakeholder dynamics have never been more complex.

To understand enterprise leadership, it helps to start with a simple image: a jigsaw puzzle.

Early in your career, you’re given a piece of the puzzle. Over time, as trust and performance grow, so does the number of pieces you’re expected to connect. Once you reach the enterprise level, leadership is no longer about building your piece of the puzzle. It’s about understanding how the pieces fit together and, eventually, being accountable for the whole picture.

People trust leaders at this level when they believe you see the whole puzzle, not just your section of it, and that you’re willing to act in service of the whole, even when that creates tension, difficult tradeoffs, and challenges.

Where Enterprise Trust Breaks Down

A few years ago, I thought it would be fun to put together a puzzle depicting the Atlantic Ocean. Five thousand blue pieces later, I learned what many wiser puzzlers already know: putting a puzzle together sounds like a great idea until you actually do it. Then, prepare yourself. You’ll want to quit. You’ll insist the puzzle is missing pieces. You’ll look at the picture on the box dozens of times, because it’s surprisingly easy to lose sight of what you’re trying to accomplish.

Enterprise Trust isn’t so different.

It’s easy in theory, but much harder in practice, and over the years, I’ve seen common barriers to building this type of trust.

One barrier is communication. When ideas become too wordy or overloaded with information, the point gets buried, the value gets lost, and audiences struggle to see the connection between what’s being said and what matters at the enterprise level.

In other cases, the barrier is behavioral. For example, a company freezes travel to manage costs, but some leaders quietly decide they’re the exception. Or leaders publicly support enterprise decisions while privately expressing disagreement or reluctance to follow through.

There are also real structural barriers. Some leaders are expected to operate with enterprise judgment despite limited access or visibility into key decisions or information. Others work in global organizations where incentives are misaligned, structures reinforce silos, and collaboration is the exception rather than the norm.

The biggest barrier of all is often a very human one: what leaders are actually rewarded for. Leaders are incented to produce certain results, and when they don’t, there are consequences. Enterprise Trust sometimes requires accepting short-term personal downside for long-term enterprise good, and even strong leaders wrestle with that tradeoff.

Practical Actions Leaders Can Take to Build Enterprise Trust

The good news is this: Enterprise Trust isn’t a personality trait. It’s not something you either have or don’t have. It’s a skill that can be learned, and to grow in this area, start with a few practical actions:

Make decisions through the lens of enterprise value.
Before deciding, ask: Does this create value for the company—or mainly for me, my role, or my function?

Use the puzzle to filter priorities.
When everything feels urgent, ask: Which of these help complete the enterprise puzzle? Deprioritize what doesn’t.

Pressure-test ideas before taking them up.
Before going to the CEO, ask: Who else have I consulted with? What perspectives did we consider? Enterprise trust grows when leaders look beyond their own view.

Consider enterprise impact, not just local impact.
Ask: How will this land with employees across geographies, time zones, cultures, and functions—not just in my area?

Evaluate investments as if the money were yours.
Before approving spend, ask: Is this the best use of enterprise dollars? What’s our track record with similar investments?

Check whether your results contribute to the whole.
Periodically step back and ask: How do my results impact enterprise performance?

Collaborate with purpose, not optics.
Don’t involve others just to be inclusive. Ask: Who actually needs to be involved to get the right outcome?

Make tradeoffs visible.
When choosing one priority over another, say what you’re deprioritizing and why.

Model enterprise constraints consistently.
If the company is tightening spend, travel, or hiring, operate the same way yourself. Exceptions speak loudly.

Ask one final question before acting:
If I were responsible for the entire company, would I still make this choice?

Growing Enterprise Trust Is the Job of Senior Leaders

Growing Enterprise Trust doesn’t mean acting like the CEO when you’re not—you’re still there to do a specific job and deliver results. But at senior levels, leaders are trusted with far more than their own piece of the work. They’re trusted with decisions that shape the enterprise as a whole—the entire puzzle.

That’s why this kind of trust is hard to earn and even harder to maintain. When decisions affect thousands or even millions of people, the standard is higher. Leaders must show they can put the puzzle first, not themselves.