Don’t Dive Deep Until You Do This First
Picture this: A brilliant VP spends three months analyzing supply chain inefficiencies. Her team produces beautiful dashboards, comprehensive reports, and detailed recommendations. The only problem? She’s solving the wrong problem entirely. The real issue is a pricing model that makes the product unprofitable regardless of supply chain optimization.
This scenario plays out in organizations every day. In fact, companies waste $399 billion annually on ineffective meetings, many of them diving deeply into the wrong things. That’s not a typo. We’re literally burning money by diving deep on the wrong problems.
Here’s the uncomfortable truth that challenges one of Amazon’s most powerful principles: Diving deep without first mastering strategic questions is leadership malpractice. And in 2025’s ruthless environment—where leadership roles are being disproportionately cut, with middle management accounting for nearly a third of recent layoffs—it might just cost you your job.
Being Thorough Can Be a Fool’s Errand
We’ve been taught that thoroughness equals excellence. That diving deep demonstrates commitment. That analysis prevents failure. But the data tells a different story.
Consider BlackBerry’s spectacular collapse. Their engineers dove deep into perfecting physical keyboards and tactile feedback, among other features, while ignoring broader shifts to touchscreen devices and app ecosystems. They built the world’s best typewriter while the world was buying televisions. Stock price: $147 to under $10. Market share: 50% to less than 1%.
Or consider Kodak’s demise. They dove deep into perfecting film quality, achieving extraordinary chemical innovations and color accuracy that photographers loved. They held 90% market share in film. But while they analyzed film emulsion formulas, they delayed aggressively pursuing digital photography despite inventing the digital camera in 1975 and recognizing its potential. Result: bankruptcy in 2012 after 131 years in business.
The pattern is consistent: leaders confuse motion with progress. They dive deep to feel productive while avoiding the discomfort of admitting they might not know where to dive.
Here’s what the research shows: 72% of business leaders report that excess data has actually limited their decision-making ability. We’re drowning in analysis while thirsting for clarity.
Don’t Question Everything… Just the Right Things
Now contrast this with how transformational leaders operate.
When Intel faced extinction from Japanese memory competitors, Andy Grove didn’t commission another market analysis. Instead, he asked his co-founder one question: “If we got kicked out and the board brought in a new CEO, what would he do?”
The answer — ”Get out of memories” — led to Intel’s pivot to microprocessors. Revenue during Grove’s tenure: $1.9 billion to more than $26 billion.
This isn’t an isolated example. Reed Hastings built Netflix by asking questions that redirected energy rather than generating more data. His favorite: “What would happen if we cannibalized our own business?” Stock appreciation during his tenure: over 4,000%.
Satya Nadella transformed Microsoft from a “know-it-all” to a “learn-it-all” culture by consistently asking: “What energizes you in your work?” instead of prescribing solutions. Microsoft’s market cap response: $300 billion to over $3 trillion.
Notice the pattern? Yes, these leaders are diving deep. But it’s more than that. They are using strategic — probing — questions to ensure they dive deep in the right areas.
The Framework That Changes Everything
After studying many leadership transitions, I’ve identified five types of strategic questions that prevent wasted deep dives:
Assumption Questions — Expose hidden beliefs
- “What are we assuming to be true that might not be?”
- “If we had to bet the company on being wrong about something, what would it be?”
Perspective Questions — Expand the aperture
- “How would our newest employee see this problem?”
- “What would our competition hope we’d do here?”
Priority Questions — Focus the effort
- “If we could only solve one aspect of this, which would matter most?”
- “What’s the smallest change that would make the biggest difference?”
Resource Questions — Reality check
- “Do we have the capabilities to execute even if we find the perfect solution?”
- “What would we have to stop doing to do this well?”
Success Questions — Define the target
- “How will we know we’ve succeeded?”
- “What does ‘good enough’ look like here?”
In the Leadership Superpowers framework, this shows up as the distinction between Direction (making sure everything comes together) and mere activity. It’s the difference between exercising your Judgment superpower — having the right goals and taking the best paths — versus exhausting your Execution superpower on the wrong mountain. Strategic questioning activates your Skepticism (don’t be deceived; focus on essentials) and Patience (take the necessary time to get things right) powers in service of Discernment.
2025 Is Creating Urgency For You
The stakes have never been higher. With over 80,000 tech workers laid off in 2025 so far, organizations are eliminating what Amazon’s Andy Jassy calls “bureaucratic dead weight” — leaders who create analysis paralysis rather than driving decisions.
The rise of AI has paradoxically increased the importance of strategic questioning. While 96% of leaders acknowledge AI improves decision quality, only 1% of companies have reached AI maturity in decision-making. Why? Because AI can process data, but it can’t ask, “Should we be looking at this data in the first place?”
Here’s your new reality: McKinsey research shows that decision-making process quality influences outcomes six times more than analysis quality. Let that sink in. How you decide matters 6x more than how deeply you analyze.
Start by Stopping
So how do you implement this without becoming the leader who questions everything and decides nothing?
Start with Colin Powell’s 40-70 rule: Make decisions when you have between 40% and 70% of the information you wish you had. Less than 40% and you’re gambling. More than 70% and you’re probably too late.
For every deep dive request, first ask:
- “What decision will this analysis enable?”
- “What would we do differently if we knew the answer?”
- “Is this the most important unknown right now?”
If you can’t answer these clearly, you’re about to waste resources. And worse, precious time.
The transformation can be dramatic. Organizations that implement strategic questioning frameworks report cutting decision-making time by 60% or more. Why? Because half the deep dives disappear when teams realize they’re really just expensive ways to postpone difficult choices.
You Can’t Make the Moves You Can’t See
The leaders thriving in 2025 aren’t the ones with the most data or the deepest analysis. They’re the ones who ask better questions than their competitors.
This week, try this: Before your next deep dive, spend 30 minutes writing down every question you can think of about the problem. Share them with your team. Group by themes and rank them by how much they cut to the core of the issues. You’ll be amazed how often the real insight and progress emerges without a single spreadsheet.
Remember: In a world drowning in information, the scarce resource isn’t data — it’s knowing where to look. Master the questions first. The deep dives will take care of themselves.
The choice is yours: Waste months diving into the wrong problems, or invest days asking the right questions. In today’s environment, that choice might determine whether you’re leading a team next year or updating your LinkedIn profile.
What question have you been avoiding that could change everything?
Your Next Step
Here’s what I’ve discovered through decades of technical leadership: Most leadership advice fails because it ignores context.
The same communication training that transforms one leader falls flat for another. The delegation workshop that works for a startup founder confuses a Fortune 500 director. The strategic thinking course that elevates a technical leader bores an operations manager.
Why? Because the moves that make the biggest impact depend entirely on your specific situation.
I’ve systematized this insight into a framework that identifies which leadership capabilities create maximum impact for your exact context. It’s how I help leaders stop wasting time on generic development and start focusing where it counts.
Knowing where to dive deep comes from great Judgment and Acuity.
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Best,
— Gregor
