When was the last time someone made you rethink a decision instead of just nodding along?
At senior levels, problems rarely show up as open disagreement. They show up as silence, polite agreement, and meetings that sound like status updates instead of real discussions.
It’s not that your team doesn’t care. It’s that your title starts speaking louder than your questions.
Over time, the leader’s world becomes strangely quiet. Less pushback, fewer second questions, more “you’re right” and slowly, clarity begins to blur. Decisions still get made, but the thinking behind them gets weaker, because it’s happening in one head instead of many.
Real leadership isn’t about having all the answers. It’s about creating a leadership feedback culture where the best answer can survive honest challenge.
From Cheerleaders to Challengers: Designing Your Feedback Circle
Most leaders don’t consciously ask for cheerleaders. They simply stop noticing when challenge disappears.
The pattern is subtle:
- People start editing themselves before they speak.
- Reviews become presentations, not conversations.
- The loudest voice in the room is the hierarchy, not the ideas.
Reversing that pattern is a deliberate act. It needs structure, not just intent. Think of it as designing your own “clarity system” around four shifts.
1. Shift from comfort to constructive friction:
Motivation feels good. Agreement feels good. But clarity often arrives wearing uncomfortable shoes.
Create at least one space in your week where friction is expected, not avoided. A standing review with 3–4 people whose job is not to please you, but to pressure-test your thinking.
Set a simple rule for that room: “Assume the decision can be improved. Your job is to show me how.”
You’ll notice something interesting.
The first few meetings feel slow and awkward. Then, as people realise they won’t be punished for disagreeing, the quality of debate – and your confidence in the final call – rises sharply.
2. Shift from unspoken rules to explicit permission
Most teams don’t challenge their leader for one basic reason: they’re not sure it’s safe.
You may think you’ve said, “Please be honest with me.” But culture doesn’t follow words; it follows consequences.
Make permission visible and specific:
- Say clearly, “In this discussion, I’m not looking for agreement. I’m looking for blind spots.”
- When someone respectfully disagrees, don’t rush to defend. First ask, “Tell me more. What are you seeing that I’m not?”
- When their challenge improves the decision – even slightly – acknowledge it publicly.
That single move changes the story in people’s heads from: “If I disagree, I’ll be labelled difficult” to “If I disagree thoughtfully, I add real value here.”
Public credit for useful pushback is one of the fastest ways to reset norms. Do it consistently and you’ll see more second questions, not fewer.
(You can even link that behaviour into leadership development – for example, when you next update your internal competency model or work with a change management coach.
3. Shift from noise to structured reflection
When calendars are full, reflection becomes accidental. It happens in car rides, hotel lobbies, or not at all.
But complex decisions don’t suffer from lack of effort; they suffer from lack of thinking time. More information, more dashboards, more meetings – none of that guarantees better judgment.
Build a simple weekly thinking ritual:
- Block one quiet hour: No calls, no Teams pings, no email. Guard it like a client meeting.
- Ask three brutal questions:
- “Where am I deciding alone when I should be deciding with others?”
- “Which recent decision went through with too little challenge?”
- “Who in my team is quietly worried about something I’ve already signed off?”
- Capture one action: It might be inviting a different voice into a review, revisiting a rushed assumption, or asking for a fresh scenario from finance or operations.
Over time, this ritual transforms how you show up in meetings. You start listening for what’s not being said, not just what is. You start asking the second question yourself and others slowly learn that with you, deeper thinking is never wasted.
4. Shift from random bravery to reliable mechanisms
In many organisations, honest feedback relies on individual courage. Someone occasionally gathers the nerve to speak up, and everyone hopes it goes well.
That’s a fragile system.
Leaders who consistently get the truth don’t depend on bravery. They install mechanisms that make honesty part of the process, not a personality trait.
Examples:
- Red-team reviews for major decisions, where a small group’s explicit role is to challenge assumptions and highlight risks.
- Pre-read questions sent before key meetings: “What are your top 2 concerns about this decision?” This lets people think before the hierarchy enters the room.
- Shadow boards or reverse-mentoring forums where younger leaders can offer an unfiltered view of decisions that affect them.
- Anonymous pulse checks after major changes to see whether people truly understand the “why” and still have concerns.
Each mechanism sends the same quiet signal: “Challenge is part of how we operate here.”
Tie these mechanisms to your leadership routines – quarterly strategy reviews, annual planning, large-capex approvals. The more important the decision, the more built-in challenge it should carry.
5. Shift from title-led influence to lens-led influence
The higher you rise, the more your personal lens becomes the organisation’s lens. Not just what you decide, but how you decide.
If you react defensively to challenge, people learn that good news is safer than accurate news. If you reward only those who agree quickly, you attract speed but lose depth.
Start modelling the behaviours you want the organisation to copy:
- Say “I don’t know” when you genuinely don’t.
- Change your mind in public when new information is compelling.
- Separate the idea from the person – appreciate the intent even when you reject the proposal.
- Ask people, “What are we missing?” before you close a discussion, not after.
Over time, your leadership team begins to mirror this posture. They, in turn, create similar spaces for their teams, and the culture slowly shifts from yes-men to thinking partners.
That’s how a feedback culture scales – not through slogans, but through consistent modelling at the top.
6. Shift from information hoarding to shared sense-making
Senior leaders often sit on the heaviest mix of information: market signals, board expectations, internal politics, and operational constraints. When this stays locked at the top, teams see only fragments and pushback becomes shallow because they don’t have the full picture.
Share more context, not more pressure.
- When you present a decision or a direction, walk people through your reasoning.
- What trade-offs did you consider?
- What risks were you most worried about?
- Where are you still unsure?
Invite your team into the thinking, not just the execution.
You’ll notice that the quality of their questions improves dramatically. They stop nit-picking small details and start engaging with the real levers – capacity, cash, capabilities, customer impact.
That’s when feedback becomes strategic, not just tactical.
7. Build your personal “truth circle”
Even with all these structures, every leader needs a small group that can say, “You’re missing something,” without fear.
Think of it as your personal truth circle – 3 to 5 people who:
- Understand your context.
- Care more about the organisation’s long-term health than about pleasing you.
- Are willing to ask the second, third, and fourth question.
They might be senior colleagues, board members, external advisors, or long-term partners. What matters is that with them, your title sits outside the room.
Be explicit about what you want: “Your job with me is not to be nice. It’s to keep me honest.”
If you already have someone who plays that role, make time with them non-negotiable. If you don’t, that might be the most important leadership hire you make this year.
For a deeper, practical walkthrough on building this habit, you can watch the full video here – link this phrase to the YouTube episode where the practice is explained step by step.
Clarity at the top is rarely a knowledge problem. It’s a conversation problem.
When you surround yourself only with agreement, you get speed without depth. When you invite thoughtful challenge, you get fewer comfortable meetings and far better decisions.
So the question isn’t just, “Am I a decisive leader?” The sharper question is, “Have I made it truly safe for people to change my mind?”
Because the strongest leaders aren’t protected by silence. They’re sharpened by honest voices – delivered with respect, backed by facts, and welcomed by a leader who understands one simple truth:
Real authority doesn’t come from being right alone. It comes from building a culture where the right answer has every chance to emerge.
