When “I Don’t Know” Changes Everything

And no, I didn’t always think this way. Even years into leading tech teams, I thought leadership was about answers. I used to believe the person in charge should be the first to spot a problem, the first to fix it.

That illusion lasted right up until my scope grew faster than my hands could keep up. At our next standup, I tested how to lead with questions by replacing the generic “anything else?” I tried something more pointed: “What’s the biggest thing slowing you down?” Within minutes, someone surfaced a system constraint I hadn’t even heard about. Turned out several people were blocked by a permissions hiccup no one wanted to admit was slowing them. A simple, specific question did more for progress than all my attempts to preempt issues ever had.

Curiosity isn’t optional. It’s survival.

Systemic Pressure vs. Questioning Power

The reality is, when your scope stretches across more domains, detail gets diluted. You’re fielding requests from three teams, juggling fires none of them warned you about, and somewhere in there you’re supposed to have a crisp answer ready for everything. When things move fast, it’s easy to skip context, default to gut choices, and just keep meetings rolling. I’ve seen it in real time. When time is tight, we fall back on familiar choices and ignore uncertainty—hurting real learning and better decision making Nature. The shortcut feels safe. Until things break and nobody knows why.

Honestly, being out of the loop feels uncomfortable. About a year ago, I was getting pings on projects I’d barely seen, pretending I understood blockers just to keep momentum. I thought acting certain would fill those gaps. It didn’t—it just made my assumptions invisible, and later, expensive.

Questioning from curiosity isn’t just a feel-good coaching move. First principles questioning—where you dig for what’s actually happening underneath—works because information lives with the people touching the problem. If you ask the ones doing the work, it’s hard for anyone (yourself included) to hide behind assumptions. First-principles thinking really does stop the BS.

But it matters how you ask. Lazy prompts like “Need anything?” just get me vague shrugs and non-answers; sharp, focused questions expose what’s real. When I’m tired, I catch myself tossing softballs; the feedback matches—just surface level. I’ve learned to reframe: being specific signals you care about what’s beneath the veneer.

You might worry that asking deeper questions chews up precious minutes or makes it look like you’re not in control. Try a five-minute pause ritual before you commit. Flip that thinking—high-quality questions multiply leverage, raising your decision quality and dropping expensive mistakes. Slower is actually faster when you count up the detours you avoid.

Practical Question Toolkits That Change Outcomes

Assumption and evidence checks are vital. This is where stubborn mistakes hide—buried under “I thought…” or “it should’ve…” and waiting to trip you later. If you ask, “What facts do we actually have?” you catch missing data or logical leaps before they breed deeper issues—including a quick projection bias check. One time, a simple check during a rollout saved us from deploying to prod without full observability—the team had assumed migration was done, but a quick evidence prompt surfaced a missing dependency. Over the last quarter, I counted five launches where these same prompts avoided hours (or days) of debugging bad rollouts. Not flashy, just cumulative weeks saved.

Instead of peppering standups with “How’s it going?” swap in something pointed about blockers. “What’s in your way right now?” unlocks truth you rarely get from status fluff. The room shifts—reporting turns into problem-solving. It’s a small switch, but specificity turns updates into actual momentum.

And when your team’s creative energy feels flat—options shrink to one safe plan—creativity prompts crack things open. Listening shifts from ‘active’ to actual—inclusive facilitation in remote meetings helps balance airtime. I’ve watched quiet engineers who rarely speak up respond to “What’s an approach nobody’s mentioned?” Not everyone jumps in right away, but the room changes: people pause, think harder.

Sometimes the best idea is from someone who’s never led a build before. I remember a migration session last fall—one junior engineer floated a rollback strategy nobody had considered. We tried it. It worked. You start getting sharper solutions if you’re willing to sit in the silence and listen. You have to practice patience—sometimes it feels awkward, but the reward is new options.

Decision making with questions works like a debugger. Just like stepping through logic to find a bug, you trace through context, blockers, and evidence until you spot the real issue. The difference is, with questions, you’re debugging people and plans, not just code. It slows you down, but that’s almost always what ends up mattering.

Scripts for How to Lead with Questions: Where Curiosity Meets Ritual

One-on-ones easily become comfort zones—both sides nodding, talking about the week, skipping over what matters. I start with questions that move us from chit-chat to clarity and turn 1:1s into feedback loops. Instead of “How are you feeling about things?” I’ll open with, “What’s something you wish I noticed earlier?” or “What’s the decision you’re most wrestling with?” It feels exposed, but surfacing real context lets ownership land where it should. If you’re used to keeping things breezy, it takes a bit of nerve to wade into real blockers. But you get breakthroughs, not just updates.

In standups, it’s tempting to let the “what did you do yesterday?” routine run on autopilot. I started trading that for “What’s one thing slowing you down?” and it changed the whole meeting. When the room stops performing for status and starts collaborating on obstacles, you see actual progress.

Planning and reviews are where assumptions sneak in the back door. Anchoring decisions in first principles—by literally asking, “What are we assuming, and what evidence do we have?”—forces us to say it out loud and write decision-ready stakeholder updates. Deliberately naming assumptions before you commit lets teams spot risks upfront, just like prospective hindsight does for pre-mortems. Suddenly “I thought that was handled” turns into a list of open questions—before they catch us later.

With incidents, the urge is to get to a root cause fast so everything feels under control. But slowing down matters most here. I try to model collaborative inquiry, resisting “this must’ve been X again” and instead asking, “What’s the full sequence as we know it—where are the gaps?” Admitting I don’t know the answer helps the team consider more angles. That call-back to earlier: leading by asking questions, not answers, is where you draw out every detail and let the team own the detective work. Premature certainty kills learning; taking the time actually shows confidence.

Practicing Questions: Building the Habit and Seeing the Impact

If you actually want to stick with this approach, it needs to fit into day-to-day—not just live on a poster or in someone’s notebook. Here’s the practical bit. Set a lightweight “questions to ask” reminder before meetings. Nudge yourself with a quick calendar check once a week—“Did I get beneath the surface?” Build a shared list of go-to prompts for your team. I started adding mine into docs and Slack. Over time it just becomes second nature.

How do you know it’s working? Look for sharper decisions, fewer last-minute reversals, and watch cycle times edge downward. You’ll see blockers show up earlier and defects tied to missed assumptions shrink. The technical bit—iterate what gets measured. Are you getting fewer “we need to redo this”? Does feedback show up on time, not just too late? If the results feel squishier than you expect, persist. Many times, I only realized the questioning habit was helping when things just broke less often. Not because the metrics screamed “Success.”

Think back to that room where “I don’t know—let’s talk it through” changed everything. The trick wasn’t losing confidence—it was modeling humility and making space for slower, collective thinking. For what it’s worth, even now I sometimes slip back into old habits and catch myself filling silences with guesses instead of questions. Haven’t figured out how to fully stop that, but the room always tells me when I need to try harder.

Learn how to lead with questions. Raise the room. It’s the reason the team shows up for you.