Why Chiefs of Staff Should Always Ask the Uncomfortable Question
When I first started as Chief of Staff, speaking up felt intimidating. Everyone else had titles like VP, Director, or CEO—and more years of experience than me. My questions seemed small compared to their big plans.
But then I realized something important: my job wasn’t about matching their seniority or experience. It was about noticing gaps and raising issues no one else saw. My unique position allowed me to spot subtle risks, potential misalignments, or flawed assumptions.
As a Chief of Staff, your real power isn’t in knowing all the answers—it’s in asking the right questions, especially when they're uncomfortable.
Here's why your perspective is not just helpful—it's critical.
Your Unique View is Exactly What Leaders Need
Chiefs of Staff don’t own a single department. Instead, you sit between teams and functions, seeing connections busy executives miss. You notice when Marketing’s new campaign timeline conflicts with Product's release schedule or when Sales' ambitious targets don't sync with operational capacity.
Other leaders often prioritize their immediate team or departmental outcomes. It’s not that they’re shortsighted—they’re just naturally biased toward what’s most relevant to their direct responsibilities. But you have the privilege (and responsibility) of seeing the bigger picture. You’re the connective tissue of the leadership team, tasked with identifying contradictions, misalignments, and potential bottlenecks that others are likely to overlook.
Because your perspective isn't limited by departmental goals or biases, you're uniquely positioned to ask important questions like:
“How will this decision impact teams not directly involved?”
“What unintended consequences could arise from implementing this?”
“Have we really considered how this aligns with our stated long-term strategy?”
These aren’t trivial questions. They're crucial checkpoints that help leadership teams avoid costly oversights. Your role isn’t secondary—it’s foundational.
How to Ask Questions Without Creating Friction
One of the biggest reasons Chiefs of Staff stay quiet is the fear of creating tension. But good strategic decisions thrive on constructive tension. Healthy friction prevents groupthink and sparks deeper insights.
The key to raising important questions without provoking unnecessary defensiveness is how you frame them. It’s not about bluntly challenging authority—it's about strategic curiosity.
Try approaching conversations with a genuine intent to understand, clarify, or refine the strategy rather than to critique or undermine. For instance:
Instead of saying, “I think this plan overlooks key risks,” you could ask, “How are we addressing potential risks in this plan?”
Instead of “This decision seems rushed,” ask, “Can you walk me through the considerations behind this timeline?”
Rather than “I disagree with this approach,” try, “What makes us confident this approach is the right one?”
Questions structured this way feel collaborative rather than confrontational. They encourage reflection, leading to richer discussions, stronger alignment, and better-informed decisions. This framing establishes you as an ally, someone who cares deeply about the success of the team rather than someone creating roadblocks.
Good Questions Create Healthy Tension and Better Outcomes
Harmony feels good. It’s comfortable, reassuring—and often dangerous. Too much harmony can lead teams directly into groupthink, where no one dares question assumptions. Strategy sessions dominated by consensus rarely surface hidden threats or opportunities. They settle too quickly on decisions that seem obvious but might overlook significant complexities.
As Chief of Staff, your responsibility includes disrupting complacency. Your questions serve as gentle wake-up calls. They force leaders to revisit their assumptions and refine their reasoning. Initially, this tension might feel uncomfortable, but teams eventually learn to appreciate it.
Think about the most effective leadership teams you’ve seen. They aren’t necessarily those who agree immediately, but those who rigorously debate and refine their strategies. Your questions stimulate exactly this type of productive dialogue. Healthy tension isn't something to fear—it's something to cultivate actively.
Final Thoughts
Chiefs of Staff often think staying quiet is safe. But silence doesn’t serve your team—it weakens strategy. Your real value lies precisely in your willingness to ask difficult questions, creating necessary tension that strengthens decisions and clarifies strategic intent.
Trust that your unique vantage point gives you valuable insights others simply don't have. Embrace the discomfort of asking tough questions, and you'll build stronger, clearer strategies that genuinely drive your organization forward.
