There’s a moment in every leadership conversation—usually just after a strategic decision has
been made—when someone hesitates. Maybe they look down. Maybe they pause just a little
too long before nodding. It’s subtle, almost invisible.
And then they say nothing.
That moment? That’s not harmless.
That’s a missed question—and more often than not, it’s a crisis waiting to happen.
Silence Isn’t Buy-In
I see it all the time during offsites around new initiatives. What gets left unasked will
eventually surface—just with more mess, more emotion, and more consequences.
Too many executive teams operate under a false sense of agreement. No one speaks up, so it
must mean everyone’s aligned… right?
Not quite.
In reality, missed questions become:
● Unvoiced concerns
● Sideways conversations
● Unclear execution
● Broken trust
● Leadership fatigue from cleaning up avoidable messes
Alignment isn’t about everyone nodding in the room—it’s about everyone asking the right
questions before decisions are made.
Questions Are the Early Warning System
Healthy executive teams embrace hard questions because they know questions are the earliest
indicators of clarity gaps.
● “What does success look like here?”
● “Who’s actually responsible for this?”
● “Have we told the rest of the team how this affects them?”
● “Does this align with our core values?”
When those questions go unasked, the team might keep moving—but they’re driving with
fogged-up windows. Eventually, someone hits something.
Vulnerability-Based Trust Makes Questions Safe
In his book, The 5 Dysfunctions of a Team, Pat Lencioni states: You can’t have healthy
conflict or true clarity without vulnerability-based trust. And trust isn’t built on
perfection—it’s built when leaders are safe enough to say:
● “I don’t know.”
● “I’m not sure I understand.”
● “Can I push back on that for a second?”
If your team doesn’t feel safe to ask tough or clarifying questions, you don’t have a performance
issue—you have a trust health issue.
And without addressing it, you’re inviting chaos and politics into your organization and that will
disrupt growth and productivity every time.
Every Leader Needs to Normalize the Ask
Healthy executive leadership isn’t about always having the answers. It’s about building a culture
where it’s safe—and expected—to ask the questions that keep the wheels from falling off.
At your next executive meeting, try this:
● Start by asking, “What’s the question we’re not asking right now?”
● Invite dissent by saying, “Push back on this—what are we missing?”
● Create space for follow-up: “What’s unclear, still confusing, or feels unaddressed?”
You’ll be amazed at how often a crisis is avoided just by getting one honest question on the
table.
Don’t Wait for the Crisis
The cost of missed questions is never immediate. That’s what makes them dangerous. They
hide in the quiet corners of meetings and show up later as confusion, misalignment, missed
deadlines, politics or sideways energy.
At CollectiveCo, we help executive teams lead with clarity, health, and rhythm. Because when
leaders build trust and normalize hard questions, they don’t just avoid crisis—they build cultures
that can carry the weight of real vision.
Ask early. Ask often. And build the kind of leadership team that doesn’t fear the tough
questions—because they know the cost of ignoring them.
—
Cindy Fiala
Founder, CollectiveCo
Organizational Health | Executive Coaching | Strategy for the Long Haul