The Rookie Mistake Killing AI Teams (And How Operators Spot It Instantly)
When you're drowning in details, the answer isn't more data—it's asking the right questions (with a little help from AI).
I grabbed coffee over the weekend with David, a brilliant mentor of mine. As we shared experiences about problem-solving in today's digital environment, he dropped a line that stopped me in my tracks:
"Asking the wrong question is more dangerous than giving the wrong data."
I appreciated the insight. Look at the paradox we're facing in 2025: we have access to more information than ever, yet our teams understand core problems less clearly than before.
The rapid proliferation of AI tools bombarding us daily creates even more data to sort through. Teams are drowning in notifications, updates, and new features while missing what actually matters. And if you're part of a distributed team, you're likely facing deeper challenges that go beyond just which Slack channel to use.
To top it off, our wacky economic environment creates unspoken pressure to deliver results quickly without taking time to properly understand what's happening. All of this leads to teams obsessing over details while the real problems float by unaddressed.
Smart leaders drown in details that don't matter
I've had my healthy share of sticky situations where I was presented with a challenge and overcomplicated the solution. It's so easy to treat everything that crosses your desk as a mission-critical, all-hands-on-deck issue.
Many of my biggest fumbles have come from being asked to create proposals for people and not truly listening to what they were asking for. I'd over-engineer solutions that were out of budget and didn't solve their actual issues. When we're not listening to what people are asking for, we get involved in tasks that don't contribute to a happy outcome.
The most common reason leaders get trapped in the details is because they get lost in the day-to-day. They have a stack of work they're responsible for and move from task to task to task.
What ends up happening? Things get delegated, shuffled, and then explained away passively without actually trying to understand what someone needs. The details of the ask get used as an excuse to inquire more, gather more information, set up more calls, and include more people.
I don't think anyone who does this is doing it intentionally—but it creates a bigger issue than ever needed to be.
This challenge gets amplified in a distributed environment. If you pose a question to the void of your communication platform, it's easy to assume all eyes are on the problem. But on the other side, team members can easily ignore it, assuming someone else is already working on a resolution.
In remote setups, people often hide behind digital silence, leading to passive accountability where whoever is available focuses on the solution instead of the right person. The scattered data across platforms, cloud drives, and communication threads makes it worse—collaborators might not even know if they have access to the data or if it exists at all.
Your real problems are dragons hiding beneath broken bridges
Let me offer a metaphor that's helped me think about this challenge.
Problem solving is like building a bridge. Most teams start by analyzing what's broken on their side of the ravine—the broken planks, the weathered rope, the unstable foundation. That approach seems logical, but it's backward.
What if instead, we first envisioned the complete bridge we're trying to build? What does the ideal outcome look like when you reach the other side?
When you take this approach, something interesting happens. You start to see the real obstacle isn't the broken pieces of your current bridge. There's a dragon in the ravine—a fundamental challenge that's causing all those symptoms you've been obsessing over.
This dragon represents the real, often unspoken problem—the deeper issue causing recurring symptoms. Most teams get distracted analyzing every tree and rock along the path instead of confronting the dragon directly.
Inversion is the counterintuitive approach most leaders miss
Here's a simple mental model I use to spot the dragon: the inversion method. I first heard about this from Charlie Munger, Warren Buffett's partner and a lover of mental models.
This approach involves thinking about the opposite of what you want to achieve and focusing on how you can avoid failure rather than solely on how to achieve success.
For example, a client might keep saying "the interface isn't working for our users," and the team goes into endless tweaks. But the real problem could be that the client never defined who their actual target users are or what outcomes they need from the tool. Both sides get stuck in a cycle of minor fixes.
We can simplify by asking the client to clearly describe what a flawless outcome (or total failure, depending on scenario) would look like. Then we work backward from that vision to identify key conditions, processes, and gaps we need to bridge. This allows us to quickly compare ideal requirements to the current state and determine the root issue preventing the client from achieving their outcome.
Others might say inversion neglects more nuanced, incremental improvements needed in real-world contexts. But it's useful for much of the day-to-day challenges that many young managers face.
And remember, not every team member or client is comfortable articulating an ideal vision. That's where leadership comes in—bringing in someone who can visualize that outcome when it's required.
Diving deep often means you're diving in the wrong direction
When we dive too deep into details, we risk analysis paralysis—spending more time dissecting the problem than solving it. Our instinct when presented with a hard question is to roll up our sleeves, delegate responsibility, create tickets, block out time, and book calls.
But sometimes a problem is actually just a question disguised as a problem.
Ask the person who brings up the issue if they understand why it's a problem. It seems simple, but I've observed this missing step for years. Put yourself in your peers' or clients' shoes and try to identify if there's an understanding gap that's causing them to shape a question into a problem.
One trap to avoid is the relentless pursuit of drilling down into every detail until you uncover the deepest root cause. There's a time and place for that, but effective leaders need to know when to step back, make a decision, and communicate priorities. This is where trusting both data and your personal intuition comes into play.
Some details change everything while others waste your time
Not all details are created equal.
The details that matter:
Directly impact primary objectives (like a consistent drop in user conversion rates that reduces revenue)
Link to fundamental issues
Recur consistently over time (persistent software bugs affecting significant users on every update)
Are supported by reliable data
Are critical for stakeholder success
The details that distract:
Peripheral symptoms with minimal impact (occasional typos in marketing emails that don't affect campaign performance)
One-off incidents (rare system errors during unusual traffic spikes)
Lack clear data support (anecdotal comments not reflected in broader feedback)
Are irrelevant to long-term goals (social buzz that doesn't translate to improved business outcomes)
Result from misaligned focus (chasing vanity metrics like temporary increases in page views that don't impact revenue)
At the end of the day, if you're not focused on revenue goals, you'll waste a lot of time. As Winston Churchill wisely noted, "You will never reach your destination if you stop and throw stones at every dog that barks."
AI tools make spotting the dragon easier than ever before
Luckily, we're living in a time with new tools that can help us spot that dragon lurking beneath our bridges.
LLMs like ChatGPT or Claude are killer at analyzing situations and presenting approaches. Since we know which mental models work and what we're trying to identify, a simple prompt can help:
I am facing [this problem]. Here is the current situation and key symptoms: [outline the situation]. Ask a series of 'why' questions to help me identify the underlying causes.The LLM will provide insights you can use to decide how to proceed. You can even ask it to assess whether your solution will fix the problem—not to take at face value, but as an extra confidence boost combined with your intuition.
This is a no-brainer right now. We're in a gold rush in terms of tool availability and pricing. There's never been an easier time to communicate clearly to teams using these AI assistants.
Missing the real problem costs more than any solution
When we fixate on the wrong problems, the consequences ripple throughout the organization:
We invest time and resources that yield no strategic value
Confusion and internal friction develop
Core issues remain unaddressed, undermining innovation
Trust erodes in both your team and with clients
The entire organization can lose focus, resulting in diminished competitive advantage and falling revenue
Leaders should openly share their own uncertainties or mistakes during discussions about finding root problems. Often challenging problems escalate up the command ladder, but even as leaders, we don't always have the answer.
This is where emotional intelligence matters.
When a problem lands in your lap, let everyone know "we'll figure it out" without losing your cool. Always return to the basics: define the ideal outcome, assess the current state, identify gaps blocking success, and then be decisive and communicate immediate actions.
If you find yourself the de facto problem solver, remember to delegate this process to others. It's important for the team to learn and practice these skills—give a man a fish or teach him how to fish, as the saying goes.
A stolen donut reveals why we miss what actually matters
Let me close with a personal story about how focusing on the wrong issues can have a lasting negative impact.
When I was in primary school, my classmate Hope won a competition and received a donut from a local bakery. If you grew up in the '80s, you know local bakeries went hard, and that donut might as well have been a bar of gold to us eight-year-olds.
Hope kept the prized donut in a decorated box on her desk. Our class left for library time, while Jack, another classmate, stayed behind in detention for acting out that morning.
When we returned an hour later, the donut had disappeared. Our teacher singled out Jack, who had chocolate smeared on his face, and verbally berated him for stealing in front of everyone.
This story became legendary among Jack and our peer group. But years later, talking with a former classmate, we had a sad realization: Jack didn't steal the donut out of spite or malice. In hindsight, knowing what we learned about Jack's home life, he was hungry.
Our teacher didn't display leadership. Instead, she humiliated Jack and failed to identify the root problem. She missed an opportunity to get Hope another donut without embarrassing Jack, and perhaps get him some healthy food.
It's not a feel-good story, but it perfectly illustrates what happens when we focus on symptoms (a stolen donut) rather than root causes (a hungry child).
Building past the dragon requires seeing the complete bridge
I think over the next few years, teams might become too dependent on tools, letting machines resolve too many of their problems. When truly unresolvable challenges arise, it will be more important than ever to return to simple mental models and be willing to take decisive action.
Remember the bridge and the dragon. Start by defining your ideal outcome on the other side of the ravine. Compare that vision with your current reality to identify what's missing. Spot the dragon—the real problem causing recurring symptoms. Then be brave enough to confront the dragon directly and begin building with strategy and intent.
Because at the end of the day, asking the wrong question is more dangerous than giving the wrong data.
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