Leadership
The “Everything’s Fine” Trap
Jun 7, 2025
In tech, we’re trained to listen for alarms. We build dashboards to detect latency spikes, write alerts for disk usage, and monitor log streams for anomalies.
But what about the most dangerous signal of all—when someone says, “Everything’s fine”?
It sounds reassuring. No red flags. No blockers. Just progress. Until the launch fails, the demo crashes, or the team quietly combusts under the surface.
The reality is that if you’re not hearing uncomfortable truths regularly, your team isn’t honest with you. And that’s not their fault. It’s yours.
Why Your Team Isn’t Telling You the Truth
Honest information is the most valuable asset in a tech organization. But most teams operate under an invisible gag order—a mix of fear, politeness, and professional pride that suppresses early warnings.
Engineers don’t want to sound incompetent.
Product managers don’t want to disappoint.
Tech leads don’t want to look like they’ve lost control.
And even when someone tries to speak up, vague or optimistic questions shut the door before it opens. Ask, “Is everything on track?” and you’ll probably get a “yes”—even if that “yes” hides growing tech debt or a missed integration.
Recent research confirms what many of us suspect: questions that presume something is wrong get far more honest, detailed answers than general or optimistic ones. Maurice Schweitzer and Jeremy Yip found that leaders who ask this way are also seen as more competent and trustworthy.
Assume There’s a Crisis—Then Ask About It
This approach isn’t cynicism—it’s responsibility. Tech problems don’t introduce themselves. They multiply quietly, then explode.
That’s why strong leaders don’t ask, “Are there any issues?” They ask, “What issues are we underestimating?”
Here’s how to reframe your questions:
Instead of: “Is the team aligned?” → Ask: “Where are we misaligned right now?”
Instead of: “Is the API stable?” → Ask: “What’s the riskiest edge case we haven’t tested yet?”
Instead of: “Is the architecture solid?” → Ask: “Which part of this design are you least confident in?”
A minor linguistic shift. A big psychological unlock.
Five Habits of the Truth-Seeking Leader
If you want a team that gives you the truth early and often, you must earn it. Here’s how.
1. Do Your Homework
Walk into status conversations informed. Review burndown charts. Skim recent PRs. Check system metrics. The more context you bring, the more substance you’ll get.
Example: “I noticed error spikes on /transaction/create yesterday. Is that tied to Chelsea’s refactor?”
That kind of question signals, “I’m paying attention. You can talk to me about real stuff.”
2. Set the Ground Rules for Honesty
You can’t expect truth without safety. Set expectations clearly.
Example: “I’m not looking for a polished update—I’m looking for the truth so we can make the right calls together.”
It frames honesty as a contribution, not a risk.
3. Ask Like a Peer, Not a Prosecutor
Avoid interrogation mode. Be curious, not judgmental.
Instead of: “Why is this late?”
Try: “What made this one tougher than expected?”
That opens space for reflection instead of defensiveness.
4. Make It Hard to Spin
Vague updates should be uncomfortable by default. Ask for specifics: timelines, dependencies, failure scenarios. Have these conversations in person or over video. Folks are more likely to sidestep tough questions over Slack than when you’re talking live.
Example: “What part of the system makes you nervous when traffic spikes?”
5. Reward Candor with Action
When someone brings you a hard truth, show them it was worth it.
Delay a launch if it’s the right move.
Escalate a resource constraint.
Cancel a doomed experiment.
And when someone admits a mistake early? Thank them. Normalize it. Move forward.
Your reaction teaches the team whether honesty is safe—or self-sabotaging.
Why This Matters More Than Ever
Tech leadership isn’t about having all the answers. It’s about surfacing the right problems—early—and mobilizing your team to solve them.
That only happens when people trust you enough to speak up. When blockers show up fast. When the unsaid finally gets airtime.
The best CTOs I know don’t just build systems—they build truth funnels. They create cultures where hard news travels fast, discomfort is expected, and “everything’s fine” is met with a skeptical pause and a follow-up that cuts deeper.
Try This Today
Pick one conversation this week where you’d typically ask a check-in question.
Change one question in one conversation:
“What’s the part of this that worries you most?”
“What’s not going to plan that we haven’t named yet?”
“What are we not talking about that we probably should be?”
Then stop talking. Let silence work. See what surfaces.
Bottom line: In high-stakes tech environments, honesty isn’t optional—it’s oxygen. Like any vital resource, it needs to be cultivated, protected, and kept flowing.
If you want better outcomes, stop looking for reassurance. Start looking for what’s real.
Because when a team says “everything’s fine,” great leaders don’t relax—they dig deeper.
