Do your associates ever voice disagreement with you?
I read a fascinating article in the Harvard Business Review related to the book, “What to Ask the Person in the Mirror: Critical Questions for Becoming a More Effective Leader and Reaching Your Potential,” by Robert Kaplan.
The question that stood out to me was this:
“How often do your subordinates challenge or disagree with you?”
In my experience, the most effective leaders have at least a few associates who are willing to share contrarian points of view. Healthy disagreement is not a sign of disloyalty — it’s a sign of trust. When team members feel safe enough to speak up and say, “I see this differently,” the conversation shifts from being about the leader’s idea to being about the best idea. That process almost always leads to a better outcome.
It also says a lot about the leader if he or she can receive pushback without being defensive. Do you truly listen, or are you just waiting for your turn to respond? Do you welcome the refining influence of other perspectives, or do you subtly shut down the conversation? Leaders who remain curious — who ask follow-up questions instead of cutting things off — send a clear signal: “Your input matters.”
In a world of remote work, hybrid teams, and constant change, the ability for associates to challenge leadership respectfully and constructively is a key marker of organizational health.
Google’s landmark research on high-performing teams found that psychological safety, the belief that you won’t be punished or humiliated for speaking up with an idea or question, was the single most important factor in team success.
So let me turn the mirror back to you:
How often does someone on your team challenge your views?
What does that say about the way you lead?
What does it say about the level of trust you and your associates share?
If you don’t have anyone who truly healthily challenges you, why do you think no one is willing to speak up?
Photo by cottonbro studio: https://www.pexels.com/photo/carpenters-standing-at-the-table-7484160/
Do people feel safe to disagree?
Do they believe you truly want to hear their perspective?
What would the outcome be if you truly welcomed others’ observations and heard what your associates had to say?
Or perhaps there’s a different issue at play. Perhaps no one disagrees with you because they don’t have the insight or depth of experience that you do.
While this might be satisfying in the short term, your goal is to create a company that’s successful long term without being so reliant on you.
Recommended Read: Preparing Your Business For Exit is Just Good Business Strategy
In that case, your next step is to grow a team who are capable of managing their area of expertise with competency and leadership.
This frees you up to see the big picture and strategy, including your eventual exit plan.
The best leaders I know don’t need to be the smartest person in the room. They need to be the kind of leader who creates a room where the smartest ideas can emerge — even if they come from someone else.
If you’d like to grow your leadership skills or your team’s capabilities, Doescher Group is here to help you lead with confidence and ease.
Connect with one of our Executive Coaches.

