AI has made analysis abundant. You can model more scenarios, stress-test more assumptions, and surface more data than ever before. But there's a category of information AI can't provide: what's really happening on the ground, which assumptions are wrong, and what people aren't telling you.

The decisions that matter most depend on inputs that don't live in dashboards.

This has always been true, and the quality of your inputs has always mattered. But as people become increasingly reliant on AI to help with high-level decision-making, it is becoming more critical. 

The Filtered Feedback Paradox

Here's what makes this harder: as your career progresses, the truth gets harder to access.

When Rhiannon White became CEO of Clue, she expected things to continue as they were. She'd been Chief Product Officer. The team had worked together for years. They'd been through ups and downs together. Surely changing one word in her title wouldn't change how people interacted with her.

She was wrong.

Before, when she had a half-formed idea, the team would debate it. They'd challenge, spar, push back. That was the product culture; all ideas are bad until iteration makes them good.

After becoming CEO, people started saying "okay" and running off to execute. Or they'd smile, say nothing, and complain to their manager that her idea was unworkable. Both responses were reasonable because her ideas often were half-formed. But the dynamic had shifted so she could no longer think out loud.

Four weeks later, she sat in a meeting watching teams collide over competing priorities. The pressure they were under, the chaos in the pipeline, and she realised it was her fault. Her casual suggestions had become directives. Ideas that should have been debated had been treated as decisions.

This creates a paradox: the position that gives you authority to set direction also isolates you from the feedback you need to set it well.

The Relationships You Need Change As You Grow

AI has no stake in the outcome. It won't be around to own the consequences. But you will.

The unfiltered truth about what's working, what's not, and what everyone's afraid to say flows through people. And if you don't build those channels deliberately, the information won't flow at all.

The challenge is that what worked at one level in your career won't work at the next. As your career progresses, your relationship needs evolve:

Early career: Information gatherers who make their thinking visible. 
You need access to experienced practitioners who don't just tell you what to do, but show you how they arrived at their conclusions. Look for people who annotate their work, who explain the alternatives they considered and rejected, who share the mental models guiding their decisions. These might be senior colleagues willing to do working sessions where you observe their process, or online communities where practitioners share detailed case studies. The goal is to absorb judgment by watching it in action.

Mid-career: Reality-checkers who know different parts of the system. 
As you start diagnosing problems across functional boundaries, you need a network of specialists who can validate or challenge your cross-functional assumptions. An engineering lead who can tell you when your proposed solution creates technical debt. A sales director who can explain why your pricing change will kill deals. A customer success manager who sees firsthand what actually confuses users. These relationships work because they have expertise you lack, and you're explicitly asking them to reality-check your thinking before you commit resources.

Senior levels: Your personal board of truth-tellers. 
At this stage, you need a small circle, perhaps five to ten people, whose job is to tell you when you're wrong. These are people who knew you before the promotion, who have no reason to flatter you, and who care enough to be honest even when it's uncomfortable. Former colleagues are now at other companies. Advisors with nothing to gain from your success. Peers at your level are facing similar challenges. The defining characteristic: your title and position don't change how they talk to you. They'll tell you when your strategy is flawed, when you're ignoring obvious signals, when your team is more dysfunctional than you realize.

The common thread at every level: you need inputs that aren't filtered by politeness, hierarchy, or self-interest. What changes is the filtering you're fighting against: from "not knowing what questions to ask" to "seeing only one functional perspective" to "having your position prevent honest feedback."

Staying Connected to Reality

Rhiannon learned to counteract the filtering effect deliberately.

She still does a long-form user interview every week. When she moved into the CEO role, people told her it was a waste of time. She disagreed. Those conversations give her something no dashboard can: confidence rooted in real problems.

When an investor tells her to pivot to conversational UI, she can respond with specifics. "I spoke to a user last week who said..." Nothing shifts a conversation from opinion to reality faster than a concrete example.

She also developed a framework for knowing when to override her team and when to step back. She calls it "umbrella versus bus." Some decisions are like telling your kid to take an umbrella - if they ignore you and get rained on, they learn something. Other decisions are like stopping them from walking into traffic. The CEO's job is to know the difference.

But you can only know the difference if you have accurate information. And that information comes from people, not dashboards.

The higher you go, the more tempting it is to rely on summaries and reports. Resist this. Find ways to stay in contact with unfiltered information: customer conversations, frontline employees, raw data before it's been aggregated and interpreted for you.

Truth as Competitive Advantage

AI has dramatically reduced the cost of competent analysis. What it hasn’t reduced is the cost of being wrong about reality.

That knowledge flows through people - mentors who explain their reasoning, peers who challenge your framing, truth-tellers who aren't filtered by your position.

The professionals who build these networks don't just make better decisions. They make faster decisions with confidence because they trust their information.

Build the channels now. By the time you need them, it's too late.

This is the sixth article in a series exploring how AI is reshaping career progression. The next article dives into the layers that AI is taking over in jobs. If you want to go deeper, check out our free ebook: Managing your Career in the Age of AI.