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“This might be the best era there's ever been to be a tech exec. The deck that used to eat my Sunday now takes forty minutes. The analysis I used to dread is waiting for me before my coffee's cold. My team has 10 polished ideas ready before we even start brainstorming. I'm on top of more than I have ever been on top of!
Right? Surely. Pretty sure. I think. 😬?”
– Inner voice of an exec “thriving” in the age of AI
For months, I’ve had this nagging concern…
Something related to leading in the age of AI, but I couldn’t discern its shape. A client shared a recent experience that helped me finally clarify it:
His CEO asked him to design an executive offsite. He typed a one-line prompt into Claude and out came a gorgeous three-day agenda. He pasted that into another tool that turned it into an even more gorgeous deck. Done and dusted in under an hour. Glorious!
Then he walked the offsite co-lead, the COO, through it. By slide 3, he started to hear himself. Buzzwords galore. Session titles that sounded impressive and meant nothing. When the COO asked what a given block was actually for, he couldn't say, because there was no strategic thinking underneath. It was gobbledygook. Beautiful, frictionless gobbledygook, but meaningless nonetheless.
He walked out of that meeting, threw it all away, and started over: his own thinking leading the way.
What gets me about this story is that he didn't “cut corners” in any way that warrants admonishing. He did the modern, efficient, entirely reasonable thing. The output looked like his own work, even to him.
The gap only became visible when he had to show his work. (Cue all the middle school math teachers’ self-satisfied nodding.) Most execs don't get caught that fast. We keep doing the modern, efficient, entirely reasonable thing day after day almost reflexively, rarely asking, “What’s the cost? How do you know if it’s worth paying?”
The cost is you stop building your capacity, your tolerance for the core intellectual work your role exists to do.
The Slippery Slope of Smart Sand
To understand why that’s happening so easily, it helps to use the classic rocks and sand framework.
The Rocks are the core intellectual work of leadership: framing the problem correctly, weighing real tradeoffs, spotting the second-order effects, making calls under uncertainty.
The Sand is all the things on your list that are quick and easy to do. It’s tempting for a leader to fill their day with sand, because it’s easier to get to that satisfying feeling of crossing things off a list.
The prevailing narrative right now: If you aren't using AI to turn your rocks into sand, you’re falling behind.
But the more you sand down your rocks, the more automatic that shortcut becomes:
Typing in a single prompt to do competitive market analysis
Auto-generating a quarterly board meeting deck without first thinking about the highest leverage questions the board should engage with
Slacking the recruiting team “We need to hire X” without doing the groundwork to determine what makes a successful candidate
What starts as a conscious choice, an efficiency tradeoff, evolves into a default habit. I had one founder-CEO client who, when we first started working together, would prompt ChatGPT as his first step for any and all tasks. His ChatGPT habit eroded his tolerance for the hard, messy figuring out.
I notice this tendency in my kids at piano practice. The easy piece is great, because it sounds good on the first try; that one gets practiced many times. The hard piece, the one that takes try after try of not-getting-it, is the one that suddenly requires a snack break first and then a bathroom break, and then yet another stalling tactic.
For my clients, this fading tolerance shows up as a small internal ugh when something requires real figuring out. Can't AI do this? Or the ever-popular: I don't “have time” to do this right now.
I've caught myself reaching for the fast, plausible answer instead of the right one often enough to know this habit doesn't feel problematic; it feels like efficiency. But landing on the “right” answer, whether you reasoned your way there or you’re leaning on instinct, is the entire point of your role.
Reaching for fast and plausible by default makes your role pointless.
Putting The Bad Habit In Check
This may be the most defining leadership question of today: Are you choosing your relationship to the rocks intentionally, or letting your habit choose it for you?
In concrete terms, answering that question requires you to assess how you work. Run these four clarifying questions against what you shipped this week:
Am I reasoning or approving? When AI or your team brings you output, are you pressure-testing it against your own logic, or checking if it sounds plausible and hitting approve?
Did I know what "done" looked like before I asked? Can you articulate the core requirements before prompting a tool or briefing a report? If not, you haven't delegated execution: you've handed off the rock.
Has delegation crossed into substitution? Delegation keeps your strategic judgment in the loop at critical checkpoints. Substitution removes your thinking entirely and just keeps your signature.
What did I reach for when it got uncomfortable? The exact moment a problem requires hard, messy figuring out: do you sit with the discomfort or default to a quick AI prompt to relieve the pressure?
If the answers land uncomfortably, resist the urge to throw the baby out with the bathwater. (Generally, throwing babies is a bad idea.) You can retain the efficiency of AI-assisted work without giving up your deep thinking. This middle ground often lives in the reflection before the work: setting expectations, defining “done,” and grounding execution in first principles.
More on that in the next issue. In the meantime, I’ll leave you with this:
AI tools may be incredible at accelerating execution, but clarity of thought remains the premium skill. When you let smart sand digest your rocks, you forfeit the rigor you’re most valued for as a leader.
REFLECTION
Which rock on your plate right now most needs your firsthand thinking, and when, specifically, will it get it?
Run one recent piece of AI-assisted work through the thermometer above. Were you reasoning, or approving?
For the most important open question on your desk: could you say out loud what "done" looks like, before asking anyone (or anything) for the answer?
Keep reading, keep leading,
Jess
P.S. If The Left-Hand Column has resonated with you, consider supporting my work by clicking on one of the ads below. It's a small action that has a big impact!
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