While promoting his new movie, Disclosure Day, in a June 14 interview on The Daily podcast, Steven Spielberg reflected on an unexpected consequence of extraordinary success. After directing blockbusters such as Jaws and Close Encounters, he found that people stopped offering him advice. His achievement had created a kind of professional force field. Others assumed he no longer needed input, or perhaps they were reluctant to challenge someone whose judgment had already produced cultural landmarks. Yet Spielberg knew what every great leader must remember: success does not eliminate blind spots. In some ways, it makes them harder to see. “It takes a lot of work to build a team that will be honest with you,” he reflected. “That’s why I’ve had the same people in my life for so many decades.”
That observation should land hard with anyone in senior leadership. Spielberg didn’t describe a lack of access to talent because he worked with brilliant artists. He described something more subtle and more dangerous: the way success can change the behavior of the people around you. The more accomplished you become, the more likely others are to edit themselves in your presence. They soften their concerns. They hold back the uncomfortable question. They wait to see what you think before sharing what they see.
Over time, a leader can become surrounded by capable people and still be under-challenged.
Cultivating a network of truth-tellers
This is one of the quiet risks of ascending to the C-suite. Most executives do not arrive there by accident. They have built careers on judgment, resilience, pattern recognition and the ability to make difficult decisions under pressure. Those are valuable capabilities. But the very strengths that elevate a leader can create blind spots. Confidence can morph into certainty. A desire for speed can become impatience. Vision can become a form of detachment from operational reality. A passion for excellence can become an inability to recognize exhaustion in those trying to deliver it.
That is why every senior leader needs a carefully cultivated network of truth-tellers and constructive challengers. Not critics who take pleasure in obstruction, people who confuse cynicism with wisdom or chronic naysayers who drain energy from every idea. Leaders need people who care enough about the mission and are secure enough in the relationship to say, “I see this differently,” “That assumption worries me,” “You may be missing something,” or “I do not think the organization is ready for this.”
That kind of challenge is not disloyalty. It is one of the highest forms of organizational commitment. But it rarely happens by accident. As a leader, you must design it intentionally. Here are seven disciplines that help:
1. Build a deliberate challenge circle
This should be a small group of people who have explicit permission to pressure-test your thinking before major decisions are finalized. They should not all think like you, value the same things you value or approach problems through the same lens. In fact, the purpose of the group is to make your thinking more complete by bringing forward what your natural tendencies may cause you to miss.
The question is not simply, “Who will disagree with me?” The better question is, “Whose way of seeing the world makes my judgment stronger?”
That question becomes even more powerful when you examine your own passions. Our passions are the internal energy sources and personality characteristics that shape how we lead, decide, influence and contribute. They are the source of some of our greatest strengths. They also influence what we notice, what we value and what we may overlook.
If you have a Builder passion, for example, you’re likely a results-driven leader who may need someone around you who is deeply attuned to the human impact of a decision. As a visionary Conceiver, you may need someone who sees execution risk and helps you alleviate it. If you’re a risk-sensitive Processor, you may need someone who can recognize when caution has become avoidance. If you have a Transformer passion and are energized by innovation, you may need someone who understands the fatigue level in the organization created by your decisions.
Every leader should periodically ask trusted colleagues: “What would my passions cause me to overlook that your passions reveal?”
That is not a soft question. It is a sophisticated leadership query. It acknowledges that even our best qualities cast shadows and invites others to help us see how our internal wiring may be shaping the way we interpret the situation. It also makes the challenge less personal. The issue is not whether you are wrong; it’s whether your perspective is complete.
2. Separate loyalty from agreement
Too many leadership teams confuse alignment with affirmation. They believe that once the leader has spoken, the proper response is support. But premature agreement is dangerous. It can create the appearance of speed while severely weakening the quality of the decision.
A healthy executive team understands that challenging thinking is not the same as undermining your role as the leader. In fact, the most loyal people in the room may be those willing to risk discomfort before letting the organization fail.
You can make that expectation clear to your team by saying, “I am not asking you to agree with me. I am asking you to help me make the best decision possible.” That sentence changes the room. It invites judgment and reflection, not compliance.
3. Ask better questions
“Does everyone agree?” is one of the least useful questions a leader can ask. It invites silence. It rewards politeness. It allows people to hide behind the group.
Better questions create more productive dialogue:
“What assumption are we making that might be wrong?”
“What would have to be true for this plan to fail?”
“Who will experience this decision differently than we intend?”
“What are we not saying because it is uncomfortable?”
“What would our strongest competitor hope we ignore?”
“What part of this decision reflects my preferences more than the organization’s needs?”
Questions like these tell people that you are not looking for applause, you’re seeking truth.
4. Build dissent into the decision process
Do not rely on spontaneous courage. Even strong people hesitate when the power dynamics in the room are not shifted in their favor. If you want a better challenge, you need to structure it.
There is a simple way to do this. Before a major decision, assign people to examine the issue from different angles. Ask one person to argue the customer impact. Ask another to identify execution risk. Ask another to assess cultural consequences. Ask another to evaluate what could go wrong six months after implementation. Ask someone else to speak for the employees who will have to live with the decision after the executive meeting ends.
This makes dissent a contribution rather than a confrontation. It also prevents the common executive failure of evaluating a decision primarily through the lens of the people most excited about it.
5. Reward candor when it appears
Culture is most powerfully shaped in the moment after someone tells the truth. If you become defensive, dismissive or visibly irritated, the room learns. If you respond instead with, “That is a fair challenge. Say more,” the room learns something very different.
To be clear, you do not have to agree with every challenge. But you do have to respect the courage it took to offer it. A simple response can reinforce the behavior: “I had not considered that,” “I see the risk more clearly now,” or “I am not persuaded yet, but I am glad you raised it.” Those moments teach the organization whether honesty is welcome or merely advertised.
6. Look beyond the executive bubble
By the time information reaches you in the C-suite, it has often been processed, softened and packaged. You need ways to encounter unvarnished experience from frontline employees, customers, emerging leaders, former employees, board members, peers and people outside your industry. Those closer to the work often see reality before those responsible for strategy see the pattern. If you want the truth, you have to get close enough to hear it before it becomes a crisis.
7. Build and examine your own blind spot inventory
This is not an abstract self-awareness exercise. It’s a practical leadership discipline. Ask yourself:
Where do I tend to overvalue my own judgment?
What kinds of people do I find easy to dismiss?
What feedback have I heard more than once but still resist?
Where does my confidence become certainty?
What do people stop telling me when they think I have already decided?
These questions are not comfortable. They’re not supposed to be because comfort is not the measure of growth. Truth is.
Spielberg’s reflection is powerful because it reminds us that extraordinary success can create isolation. When people assume you no longer need advice, you must become even more intentional about seeking it. When your record of achievement causes others to hesitate, you must work even harder to invite challenge.
The danger for successful leaders is not that they stop being smart; it’s that success slowly separates them from the people who make them smarter. The best leaders surround themselves with people who protect them, not their ego, but the quality of their judgment.
And that’s not weakness. It’s wisdom.
This article was first published in SmartBrief, June 2026.