UpTrajectory Review
In her piece, Amy Radin discusses the challenges organizations face in making timely decisions amidst increasing ambiguity, particularly as AI takes over more execution tasks. She highlights how the fear of making the wrong call leads to a culture of excessive caution, where judgment is stifled by layers of approvals and committees. This phenomenon is becoming more prevalent as the need for quick, unscripted decisions rises.
For small business owners, this article serves as a crucial reminder of the importance of fostering a culture that encourages decisive action rather than bureaucratic delays. As AI tools become more integrated into operations, the ability to make swift, informed decisions will be vital for staying competitive. Leaders should be wary of creating an environment where employees feel they must seek approval for every decision, as this can hinder innovation and responsiveness.
Takeaway: Encourage a culture of decisive action to navigate ambiguity effectively.
From the original item — Fast Company:
I’ve watched this moment happen more times than I can count, and it plays out the same way almost every time.
Someone makes the right call. Not a reckless one. A defensible, well-reasoned call that doesn’t fit the standard playbook, exactly the kind of call the organization said it wanted when it hired or promoted this person for their judgment in the first place.
And then the people paid to say no start showing up. Not because anyone did anything wrong. Because in most organizations, saying no to something unfamiliar is the safer answer for whoever’s asked to sign off on it. A “no” rarely follows anyone home. A “yes” that goes sideways does. So the sign-offs multiply: legal review, then a name on the ExCom agenda nobody remembers adding, then a steering committee, then someone in an adjacent function who “needs to be in the loop.” Five weeks later, the call that should have taken an afternoon still isn’t made.
Nobody told this person to stop using their judgment. Nobody had to. The next ambiguous call, they run it past three people first, just to be safe. The judgment didn’t disappear. It went underground.
Here’s what’s different about this moment, and why it’s suddenly everywhere. As AI absorbs more of the execution layer, the volume of unscripted calls organizations need someone, anyone, to make has gone up fast, at every level.
The old version of judgment was mostly about knowing when to follow the rule and when to escalate the exception. That worked when exceptions were rare enough to run up a hierarchy one at a time. It doesn’t work when ambiguity is the daily condition for people two and three levels below where escalation used to start. There isn’t enough hierarchy left to absorb the volume.
I worked for a division president years ago who’d grown impatient with exactly this issue. He’d stopped trying to write a rule for every situation and started building the team around principles instead: judgment anchored to a few things everyone understood deeply, rather than a manual nobody could keep current. It looked unconventional at the time. It looks early now.
That’s the real gap, and it’s not a talent gap. It’s a capability gap, which means something specific. Organizational capability is the combined mindset, skillset, and operating conditions that determine whether an organization knows what to do next and can actually do it. Most leadership teams have addressed one-third of that equation. They’ve hired the mindset, and often the skillset. The operating conditions, the actual mechanics judgment calls have to move through, haven’t changed at all.
The org chart says you’ve hired for judgment. But the conditions surrounding that hire were built for something else: consistent execution, predictable outcomes, risk contained through process. Look at what those conditions actually reward. Governance that’s bolted onto decisions after the fact, instead of built into how the work happens, will always treat an unscripted call as a deviation to be managed rather than the point of having made a judgment hire at all. You haven’t built an organization that absorbs judgment. You’ve built a faster, more frustrated bottleneck, and you’ve put your best new hire directly in front of it.
So what does the redesign actually require? Five places to start, none of them dramatic, all of them concrete.
Redesign how you hire and promote for it. Most interview processes still ask “what would you do if,” which only tests what a candidate knows to say. Ask instead for a specific time they worked through a decision with incomplete information, then keep asking what happened next until you can see how they actually think under pressure. And watch for the bias that’s easiest to miss: a panel that selects for people who think like the panel will systematically screen out the judgment that doesn’t fit the existing pattern, which is often exactly the judgment the organization needs most.
Trace one real judgment call through your actual organizational conditions. Not the one in the org chart. Pick a recent decision that ran against how things normally get approved, and follow it: how many sign-offs, how many days, how many people who don’t normally talk to each other had to agree. If that call took longer to close than your last technology spend took to approve, you have your answer about what your organization actually rewards moving quickly.
Name what doesn’t require escalation, and ask what isn’t getting raised. Most organizations have only defined what does need to go up the chain. Everything below that line defaults to caution, because nobody said otherwise. The deeper version of this question is the one worth sitting with: what problem is someone not raising right now because they’re not sure it’s safe to? That’s not a culture question. It’s a structural one, shaped entirely by what happens to people who go first.
Protect the first defensible miss. The fastest way to teach a high-judgment hire to stop using judgment is to let the first reasonable call that didn’t pan out get treated the same as an error. People don’t learn the real rules from the job posting. They learn them from what happens after the first call that didn’t land. Watch that moment closely. It’s the one your best hires are watching too.
Change what the performance review actually scores. If reviews still weight adherence to process over the quality of calls made under ambiguity, the organization is rewarding the opposite of what it said it was hiring for. Incentives that aren’t aligned to scaled, judgment-driven outcomes will always pull people back toward the safer behavior, regardless of what leadership says it values.
The leaders who get this right aren’t doing anything dramatic. They’re tracing one decision at a time through their own organizational conditions and asking an uncomfortable question: if I hired this person for their judgment, would my organization actually let them use it? Most leaders have never asked that question about their own company. The ones who have are usually surprised by the answer.