All week, one idea kept finding its way back into my head: I’ve been very focused on saving my principal’s time… but how often am I focused on moving thinking forward?
Most often, realizations like this show up for me at 3am in a cold sweat.
Our Chief of Staff colleague, Gina Gauthier, models this beautifully. In a recent post on LinkedIn, she mentioned asking her principal, “Do I disagree with you enough?” While her point was different, the sentiment reveals the delicate dance we choreograph every day.
This forces me to confront something I already know: I default to speed. It’s how I’ve operated for years. But speed alone is only one part of leverage. Deeper leverage comes from a second layer, the one that shapes thinking, not just output. And our job is knowing when the moment calls for one, the other, both or neither.
Two modes
Most of what we do can be traced back to two fundamental modes:
Reducing friction
Expanding thinking
Saving time sits squarely in the first. Clearing clutter, accelerating workflow, simplifying paths, keeping the operation moving. It’s visible and measurable, which might be why it’s so easy to stay here.
Shaping thinking lives in the second. Framing the problem, surfacing observations and patterns, naming implications, outlining second-order effects. It’s quieter. It’s selective. And it changes decisions, not just timelines.
Both modes matter. Both create leverage. And neither works without the other.
But the work isn’t choosing a mode. The work is shifting between them… and that shift, friends, requires judgement. 💡
The real work
This is where things get interesting.
It’s never as simple as reduce friction or improve judgement, we’re constantly toggling. And this is the skill that separates seasoned Chiefs from everyone else: accurately understanding what the moment is actually calling for, then executing accordingly.
Judgement is that special sauce. The reason the guac is extra. It’s the behavior that forces you to lift your lens and operate at your principal’s level:
Will adding insight here create clarity or drag?
Is the decision still forming or already fixed?
Is this a moment for speed or a moment for meaning?
Am I completing the task or completing the thought?
Will shaping the thinking accelerate things or slow them down?
This is the part that the job description never captures: the ability to read the room, the rhythm, the decision, the mood, the stakes, then make a calibrated call.
And it’s why thinking-shaping is never about offering an opinion. I say this all the time: our job isn’t to weigh in or participate. Our job is to offer the layer our principal doesn’t have time to build: the frame, the pattern, the implication, the facts.
Anyone can move fast or respond quickly. But only a Chief with strong judgement knows when to add the layer, when to remove the friction or when to leave the moment completely alone.
Before your next move
If nothing else, this framework is an invitation to slow the game.
Before you default to your usual move the speed, the smoothing, the silent fixing, the instant perspective, take a beat and ask yourself:
Is this my instinct speaking or the moment?
Sometimes the moment calls for awareness off autopilot. A way to notice when you’ve slipped into familiar modes that no longer serve what’s in front of you.
Be curious with yourself:
What if I didn’t do my default move right now?
What if this moment needs the opposite of what I usually reach for?
What if the leverage is in restraint, or in naming the pattern, or in simply observing?
Judgement sharpens when we stop moving automatically and start moving deliberately.
And sometimes the most valuable thing you can offer your principal (and yourself) is that brief pause where you choose your move instead of defaulting to it.
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