One of the less obvious risks of becoming more experienced, successful, or advancing into senior leadership is that fewer people are willing to tell you what they really think.
It’s not necessarily because people want to avoid you; it’s often because, on the way up, we have the tendency to surround ourselves with people who agree with us, and if they are not part of the “in crowd,” they withdraw or defer. Often, something even more subtle happens. People become more careful around authority and power. They hesitate before disagreeing. They soften an opinion. They decide that a concern is probably not worth raising because it may put them at risk. Or they tell you what they believe you want to hear rather than what they genuinely see.
Over time, leaders can unintentionally create an echo chamber, which is an environment where the voices around them reinforce what they already believe instead of challenging them to examine their assumptions, test their thinking, confront the hard facts, and consider alternatives.
I believe every leader needs to intentionally engage truth-tellers. Here is a short video summarizing my thoughts on this topic.
Success Does Not Eliminate Blind Spots
I was recently reading about Sandy Brondello, the head coach of the Toronto Tempo. Brondello has an extraordinary résumé. She has won WNBA championships with two different franchises, coached the Australian national team, competed internationally as a player, and worked with some of the best athletes in the game. The WNBA describes her as one of the most accomplished coaches in international basketball and someone known for a player-centered approach to leadership.
With that level of experience, it would be easy to assume that she has most things figured out. What interests me, however, is the importance she continues to place on collaboration and interacting with people who challenge her thinking.
There is an important leadership lesson in that. Championships do not eliminate blind spots. Experience does not eliminate blind spots. Success certainly does not eliminate blind spots. In some cases, success can create the equivalent of mental calluses which make our blind spots more difficult, or impossible to see because the evidence around us seems to suggest that our instincts must be right.
The danger is captured well in a familiar quote often attributed to Walter Lippmann:
“Where all think alike, no one thinks very much.”
The more convinced we become that our past success validates our current thinking, the more important it becomes to have people around us who are willing to challenge us, and even “get in our face.”
We Need People Who Are Objectively Candid
Throughout my career, I have used the phrase objectively candid to describe the kind of person every leader should have around them.
Objectively candid people are not argumentative for the sake of being confrontational. They are not critics sitting on the sidelines waiting to find fault and pounce. They care about the person, the organization, and the outcome enough to step up and speak to what they see.
The people who have helped me grow the most throughout my career have not been the people who agreed with me. Often, they have been the people who cared enough to challenge an assumption, point out something I was overlooking, or tell me something I did not particularly enjoy hearing at the time. This includes my wife, colleagues, and even clients.
In retrospect, those conversations frequently proved far more valuable than the comfortable ones.
Nice tells me what I want to hear. Kind tells me what I need to hear.
This connects directly to a distinction I have written and spoken about before: the difference between being nice and being kind. Nice and kind are not the same thing.
Nice may tell me what I want to hear because it wants to avoid tension. Kind cares enough about me to tell me what I need to hear, even when doing so creates temporary discomfort.
Having Truth-Tellers Isn’t Enough!
There is another side to this that leaders sometimes overlook. It is not enough to say that we want honest feedback or to surround ourselves with people capable of giving it. We must create an environment where people believe it is safe to tell us the truth, even when it hurts.
Ask yourself what happens when someone challenges you.
Do you become defensive? Do you immediately explain why they are wrong? Do you interrupt before they have finished? Do you justify the decision? Do you punish the messenger, even subtly, through body language, tone, exclusion, or by never asking that person for their opinion again?
If that happens often enough, people learn to distance themselves and disengage or even depart.
Harvard Business School professor Amy Edmondson‘s work on psychological safety is particularly relevant here. Psychological safety is not about lowering standards, avoiding accountability, or simply being nice. It is about creating an environment where people can raise concerns, acknowledge mistakes, ask difficult questions, disagree, and offer candid feedback without fearing that speaking up will come back to hurt them.
In other words, you cannot demand candor while punishing disagreement.
Instead, listen carefully, thoughtfully, and objectively. Resist preparing your defense while the other person is still speaking. Ask another question before making your argument. Try to understand why a thoughtful person might see the situation differently.
Let me be blunt: we don’t need smoke blowers and suck-ups around us. They may make leaders more comfortable, but they don’t help make leaders better.
Who Has Earned the Right to Tell You the Truth?
Who in your life or organization has earned the right to challenge you? Who can tell you that you are missing something without worrying about how you will react? Who brings a perspective that complements your thinking rather than merely reinforcing it?
And perhaps most importantly, when someone is courageous enough to tell you something you do not particularly want to hear, do you make it easier or harder for them to do it again?
There is a reason experienced leaders still need coaches, advisors, trusted colleagues, mentors, and candid team members. Great leaders never graduate from needing feedback.
- Who are the truth-tellers in your life and leadership circle?
- When was the last time you deliberately asked one of them, “What am I not seeing?”
- And when they answered, did you defend yourself, or did you listen and say, “Thank you”?
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