How to Build a Leadership Team You Can Trust

Alex Draper had a problem.

As CEO of DX Learning, Draper had spent the past five years redefining leadership development through immersive learning experiences. But in March 2020, with the onset of the COVID-19 pandemic, the company’s revenue went to zero overnight.

Draper and his leadership team could have panicked. Instead, they rallied.

“Through radical honesty and clarity about what we had to change, the team collectively redesigned the business,” he says. “We pivoted fast, and here we are today.”

DX Learning navigated that pivot because, early on, Draper decided to build a leadership team he could trust. And it is important to understand that the word “trust” can be interpreted in several ways.

Merriam-Webster’s Collegiate Dictionary defines trust as an assured reliance on the character, ability, strength, or truth of someone or something.

While some might think that means showing loyalty, trust is more about character and capability. When you build a leadership team — whether it’s a group of individuals or a single person dedicated to supporting the CEO — you want people who will take responsibility and not falter in challenging situations.

“Trust is not warmth,” says Draper, author of “CARE to Win: The 4 Leadership Habits to Build High-Performing Teams.” “It’s mutual reliability, transparency, and consistency under pressure.”

CARE — Clarity, Autonomy, Relationships, and Equity — is the leadership operating system Draper has spent a decade refining. Where most frameworks stop at mindset, CARE is designed to reshape the environment itself so that high trust and high performance become the default, not the aspiration.

“If CEOs intentionally build cultures grounded in clarity, autonomy, relationships, and equity, they reduce threat responses in the brains of those they serve and unlock performance through high-trust climates,” he says. “Human skills are not soft skills. They are performance multipliers.”

The 5 Capabilities CEOs Must Trust

Heather Stone is the founder and CEO of Practical PhD, where she teaches corporate leaders how to manage relationships with their “right hand” — often a COO or Chief of Staff at the company. She created her “Getting the Right Hand Right” training because she frequently encountered executives who needed a top leader but did not know how to find, hire, and manage the position.

A key distinction for her about trust is the difference between personal trust and performance trust.

“Sometimes when we say the word ‘trust,’ we are referring to someone’s ethics, values, and integrity,” she says. “Can I trust who you are as a person? Do you believe the same things I do about honesty, diligence, hard work, and respect? Certainly, these questions are important, but the problem is that I can trust your integrity and still not trust that you will make a decision or do a task the way I want. That’s about knowledge, not integrity.”

Personal trust is about integrity, intent, and reliability. Performance trust means strategic judgment, decision-making amid uncertainty, ownership and accountability, communication and alignment, and leadership through change.

1. Strategic Judgment

For Draper, strategic judgment is about pattern recognition and trade-off thinking. When trying to assess someone’s strategic thinking capabilities, he looks for how they:

• Prioritize tasks when everything feels urgent
• Balance short-term wins versus long-term health
• Integrate multiple data points into a coherent narrative
• Seek and incorporate perspectives that are outside of their expertise

Draper also has a go-to question he recommends leaders ask as part of this assessment process: If this fails, why will it fail?

“Their answer reveals how far ahead they’re thinking,” he said.

2. Decision-Making Amid Uncertainty

Rarely do leaders have all the facts when a decision needs to be made. How those decisions are made often reflects organizational culture.

When trust exists between a CEO and their leadership team, the climate is one in which all voices are heard, and information is not hidden.

“Mutual trust is not a ‘nice’ climate, it’s a kind environment where nothing is left on the table,” Draper says. “Every debate is rich with perspective. The team speaks up early and often. Disagreement is welcomed. Silence is not acceptable.”

That type of culture creates an environment where leaders are comfortable voicing their opinions. That comfort contributes not just to what decisions are made, but more importantly, how decisions are made.

“Comfort with uncertainty isn’t about confidence, it’s about shared ownership and clarity of intent,” Draper says. “When principles are clear, decisions can be made without perfect information. When psychological safety exists, people challenge assumptions before mistakes compound. Uncertainty becomes dangerous when people are afraid to speak up. It becomes manageable when dissent is normalized.”

Stone sees immense value in leaders who can make decisions amid uncertainty and “right hands” who can take grand ideas and organize them into an implementation plan. The ability to make order out of chaos is a superpower not everybody has, she says.

“Senior leaders need to be problem-solvers, people who are willing to jump in and try to move things forward even if they don’t have all the answers,” Stone adds. “But they also need to be servant-minded, recognizing that they are a help and support for the CEO, not just a functional expert in their space.”

3. Ownership and Accountability

Like organizational culture, ownership and accountability are traits often modeled by a CEO and, ideally, mirrored throughout the company. It is essential to the business’s success that the leadership team takes ownership of decisions and actions made on behalf of the CEO and the company at large.

It’s not about blame or credit. It’s about accountability.

“Ownership is contagious,” says Draper. “If leaders deflect responsibility, culture fragments. If leaders model accountability, standards rise.”

4. Communication and Alignment

Stone has been a company president 4 times, a business owner twice, and someone else’s “right hand” 4 times. And a recurring issue she has seen throughout her career is communication that doesn’t work for both sides of a leadership pair.

For example, imagine a CEO who just hired a Chief Operating Officer. This is the first time the CEO has hired a leader at that level, and they are still learning the best practices for it. The CEO, meanwhile, is looking to get tasks off their plate as soon as possible.

The CEO routinely bounds into the COO’s office and blurts out new ideas and tasks for the COO to pursue. The COO, who is often in the middle of another project, has to quickly make the mental switch to understand the CEO’s ideas and identify action items and next steps.

It’s a challenge, and because of that ad hoc flinging of requests, the COO quickly starts to flounder.

“Most miscommunication comes from lack of structure,” Stone says. “If you want to be better communicators, set up communication structures such as reports and meetings to help you.”

Draper agrees.

Organizational alignment occurs when great communication is seen as a 2-way street, with CEOs and their leadership team empathetic toward one another. They know each other’s strengths and how to support one another’s weaknesses.

“A leader who understands their strengths, recognizes their blind spots, and consistently asks for feedback will always outperform the brilliant but unaware executive,” Draper says. “Self-awareness shortens the gap between intention and impact.”

5. Leading Through Change

“The only constant is change” is an often-quoted trope by the Greek philosopher Heraclitus, used to promote everything from mindfulness to pickup trucks, but when it comes to business, the cliché is a reality.

How leaders navigate change is indicative of the strength of trust within their organization.

There is a company Stone knows well, where the CEO is described as a quick thinker, always willing to consider new ideas. As his leadership team heard these ideas, they kept trying to shift the business’s direction to implement them.

The problem, Stone points out, is that oftentimes, the leader was just brainstorming. He wasn’t actually looking to create change, but because there was no framework for processing new ideas, he wound up causing undue change.

The problem was solved when the CEO hired a “right hand,” and the leadership team began reporting to that person. Soon, that person became a sounding board for the CEO.

“Part of her job was to hear all his ideas, brainstorm with him on possibilities, and help him focus on the few key things he wanted done,” Stone says. “The company still changes frequently, but far less often than it used to. The “right-hand” relationship was a way to preserve agility in thinking while maintaining stability in operation.”

4 Steps to Build a Leadership Team You Can Actually Trust

Draper is a firm believer that leadership is not a natural act. In his eyes, no one is born to be an effective leader.

“Under pressure, our brains default to self-protection,” he says. “We threat-scan. We tighten control. We withhold information. The higher you rise, the lonelier it becomes. Ego creeps in. And where ego dominates, trust lags. Trust becomes elusive when curiosity is replaced by control.”

But effective leadership can be taught — as can how to build a trusted leadership team. Here are 4 steps:

Step 1: Assess Capability Gaps

Ask yourself, “What responsibilities or tasks do you hesitate to delegate. What’s the reason for that hesitation?” Similarly, consider where decisions stall within your business and what role you may play in that stalling.

The answers to those questions should indicate where gaps exist — and where delegation opportunities are strongest.

“Self-awareness is the starting point of effective leadership,” Draper said. “You can’t fix what you don’t know. Assumptions are the enemy of trust.”

Step 2: Increase Strategic Exposure

How often do you include leaders in enterprise-level discussions? Remember that organizational culture is a mirror of that company’s leadership. If you expect trust from your leadership team, you must show trust first.

That doesn’t mean you need to include the team in every decision you make, but be strategic in how you incorporate cross-functional perspectives in critical decisions.

Step 3: Invest in Structured Leadership Development

Draper wrote “CARE to Win” to provide a consistent framework for how leaders can treat their teams. His belief was — and continues to be — that consistency in behavior strengthens culture. And a stronger culture creates more trust.

“Leadership is learned, not inherited,” he says. “Like art, cooking, or golf, you improve through practice. There is no perfect leader, only better ones.”

Stone agrees. She created the Right Hand Roadmap to provide structure to leadership pairs. By following formal frameworks such as those recommended by Stone and Draper and applying learnings to the workplace, CEOs and those closest to them can become better, more effective leaders.

“When you win with each other, then together you can win at business,” Stone says.

Step 4: Build Peer Accountability

One of the most important signals that trust exists within a leadership team is when peers hold each other accountable.

“I trust my leaders to bring me bad news early,” Draper said. “They trust me not to shoot the messenger. We don’t have to like each other. But we respect each other, and we know we are better together.”

With accountability, growth can occur. Without it, dysfunction compounds.

Trust is Built Through Capability

For CEOs committed to building leadership teams they can trust, Vistage Leadership Development Programs offer a structured, peer-driven environment where team members at all levels in an organization can close capability gaps, improve execution, and grow to be leaders CEOs can trust.

• The Key Executive Program helps CEOs shift focus from operational execution to shaping strategic direction by improving the effectiveness of their direct reports. It enables them to become better leaders, improve operational performance, and drive results for their business.
• The Advancing Leader Program helps CEOs depend more on operational leaders to carry out their vision. It enables them to be more effective leaders and successfully drive initiatives through proactive thinking, communication, and collaboration.
• The Emerging Leader Program helps CEOs improve execution, increase employee retention, and build future talent among frontline managers. It motivates and equips rising stars to become the next generation of leaders and reinforces a philosophy of shared values.
• The Vistage Inside Program improves the effectiveness of teams from within a single organization, helping CEOs gain alignment, increase collaboration, improve accountability, build leadership teams, and develop individual leaders across their companies — all in one program.

Through leadership development, CEOs can build the trust that empowers their teams to step up, extend their impact and drive long-term growth.

Related Insights

Learn about Vistage Leadership Development Programs available to strengthen your teams.

Use the Leadership Evaluation Guide to assess your team’s performance and potential to execute your critical initiatives. Uncover opportunities to strengthen capabilities and unlock future potential.

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