You Can’t Scale What You’re Afraid to Question
When your smartest thinkers go silent, the problem isn’t culture—it’s design. Fixing it starts with how your system handles insight.
Most companies say they want strategic thinkers.
But when someone actually demonstrates strategy (asks a hard question, challenges a decision, flags a deeper pattern), what happens?
They get labeled as difficult.
Or asked to fix it on top of their day job.
Or quietly sidelined.
The problem isn’t that your team stopped thinking. It’s that the system made it dangerous.
Last week, I wrote about what happens when curiosity becomes a career risk. The response came quickly and predictably: “Okay, so how do we fix it?”
The answer isn’t offsites or brainstorms. It’s not culture decks or motivational posters.
You have to redesign the system that punishes insight in the first place.
The real work is structural, not motivational
You can’t ask people to “think like owners” when you’ve made insight expensive. You can’t expect to foster innovation by rewarding compliance. You can’t build an effective strategy if every meeting is an exercise in pretending things are fine.
Most founders and leaders I work with want their teams to be proactive—but they haven’t built the systems to make that safe, sustainable, or useful.
Here’s how to take this from insight to tactics and create a curiosity infrastructure:
Step 1: Diagnose what’s actually broken
Start by looking at the conditions that made curiosity risky in the first place.
These are the questions I ask my clients when we’re mapping where the friction lives:
Where are incentives misaligned?
If your comp plans reward individual performance but your work requires cross-functional collaboration, you’re building in conflict.
If sales gets paid to close deals and product gets blamed when they can’t deliver, you don’t have a performance issue—you have a system issue.
What happens when someone names a problem?
Do they get thanked? Or tasked with solving it on top of their workload? Are they treated like a pain? Do they get invited back to the next meeting?
If the people naming problems keep getting burned, they’ll stop speaking up. And so will everyone else.
Who is allowed to say “this isn’t working”?
If the only voices with permission to point out friction are in the C-suite, you’ve cut off 90% of your organizational intelligence.
What problems are you not allowed to solve?
Every company has processes, relationships, and assumptions that are immune to critique. That’s usually where your most expensive dysfunction lives.
Until you can name these patterns, you can’t fix them.
Culture doesn’t change because you asked it to. Culture changes when the systems underneath it enable it.
Step 2: Rebuild with structural incentives
Once you see the pattern, stop fixing symptoms and start engineering behavior.
Shared metrics stop sabotage
In one org, sales and product were openly undermining each other. Sales overpromised features. Product withheld information to protect themselves. Everyone was exhausted.
We didn’t run a mediation. We rebuilt the comp plan. Shared bonuses tied to 6- and 12-month customer retention.
Suddenly sales cared about feasibility. Product shared roadmap insight early. Retention improved by 35%. Deal quality went up. Internal drama disappeared.
No new values statement. Just better design.
Feedback loops build velocity
Insight without action burns people out. At a foundation I worked with, team members raised operational issues—but nothing ever changed.
We built a visible decision pipeline. Every piece of input got routed, tagged, and responded to—yes, no, or not now, with reasons. People didn’t need to be agreed with. They needed to see that their thinking mattered.
Step 3: Build infrastructure that scales
The goal isn’t one good meeting. The goal is that clarity flows without having to chase it.
This is what that looks like:
- Decision-making transparency: People can see how priorities are chosen and how their input shapes them.
- Strategic escalation: Clear, safe pathways to raise issues without fear of retaliation, eye-rolls, or extra work.
- Cross-functional rhythms: Regular collaboration across departments that makes friction visible early.
- Leadership accountability: Not just for results, but for system design. The real job is removing barriers, not performing alignment.
Why most curiosity initiatives fail
They treat curiosity like a personality trait—something you either have or don’t—instead of a structural requirement for a healthy business.
What that can look like in practice is:
- Leaders ask for strategic thinking, then label it “resistance” when it challenges the plan
- High performers raise hard truths and get shut down or stuck solving the problem alone
- Innovation is talked about, but insight is penalized
The result? Silence. Disengagement. Burnout. Attrition.
And the cost isn’t just emotional—it’s operational:
- Replacing a high performer can cost up to 213% of their salary. That’s over $320K for a $150K role.
- Only 24% of employees strongly agree their opinions count at work. When they do, companies see 27% less turnover and 12% higher productivity.
- Teams with psychological safety outperform peers by up to 30% in long-term profitability.
Translation: If your sharpest thinkers don’t feel safe speaking up, your early warning system is disabled. You’re flying blind—and you may not see the iceberg until you hit it.
The good news? This is fixable.
Fix What’s Not Working isn’t a values exercise or a transformative mastermind. It’s a hands-on strategy session for founders, operators, and functional leaders who want to cut through the noise and get clarity on where friction lives—and how to resolve it.
We’ll spend 2 hours diagnosing what’s actually slowing you down: misaligned incentives, unclear decision paths, structural bottlenecks. Then we’ll translate that into a practical, resource-aware action plan that sticks.
No fluff. No culture vibes. Just operational clarity you can act on.
- Most strategy fails because the environment doesn’t support it.
- Culture isn’t a mood; it’s a reflection of what your organization makes possible.
- When sharp thinking gets buried, you pay for it in delays, burnout, and attrition.
Curiosity is your early warning system.
When it’s safe to ask hard questions, you catch issues while they’re still small. When it’s not, you find out when Q4 hits and your best people are already gone.
Ready to start solving for what’s costing you?
→ Book your Fix What’s Not Working session
About the Author
Sadie Shepard is a strategic advisor who helps growth-stage founders, leaders, & operators diagnose friction, fix what’s not working, & scale smarter. She thinks in systems, writes to surface root causes, & builds clarity into how businesses grow. Learn more at sadeshep.com.
