From “Can You?” to “When Will You?”
I caught myself the other day.
I was in a meeting, reviewing a piece of work that, if I’m being honest, would’ve taken a full team a week not that long ago.
And without thinking, I asked:
“When can you have this done?”
Not can you do this?
Not is this feasible?
Just… when?
That was the moment it clicked.
Something fundamental has shifted.
I Used to Lead with “Can You Do This?”
There was a time when my job as a leader was to assess capability.
Do we have the skillset for this?
Is this too complex for one person?
Do we need to bring in someone more specialized?
Those were real constraints. Fair questions.
Work had natural friction:
Information wasn’t instantly accessible
Drafting something polished took real time
Switching domains (say, from strategy to execution) wasn’t trivial
So “can you do this?” wasn’t just a question: it was me being a responsible leader.
Now I Assume You Can
AI changed that faster than I expected.
Today, when I look at a problem, my default assumption is:
Of course this can be done.
Not because the problem is easy, rather because the tools are now absurdly powerful.
You can:
Spin up a first draft in minutes
Pressure-test an idea across multiple angles
Fill in knowledge gaps almost instantly
So the question in my head has quietly become:
“How fast can we move?”
And that’s where I had to check myself.
The Mistake I Almost Made
Just because something is possible faster doesn’t mean it should be expected instantly.
I started to notice a pattern in my own behavior:
I was compressing timelines without realizing it
I was skipping over the “thinking” part and jumping to delivery
I was treating speed as the default, not the advantage
And that’s a dangerous place to lead from.
Because AI didn’t remove complexity, it just made it easier to start. For many, starting is the hardest step.
How I’ve Had to Level Up as a Leader
I’ve had to consciously adjust how I show up.
1. I Ask Better Questions Now
Instead of:
“When will this be done?”
I try to ask:
“What’s the smartest way to approach this?”
“Where does AI actually help here and where not?”
“What part of this still requires real thought?”
Because the real risk now isn’t slowness.
It’s false confidence from fast outputs.
2. I Value Thinking More Than Speed
Ironically, AI has made thinking more valuable, not less.
Anyone can generate something quickly.
Not everyone can:
Frame the problem correctly
Identify what actually matters
Decide what not to do
So I’ve started rewarding:
Clarity over volume
Judgment over output
Intentional pacing over rushed delivery
3. I Try Not to Collapse Everything Into Urgency
This one’s hard.
Because when everything looks faster, it’s tempting to treat everything as urgent.
But I’ve learned:
Just because we can move fast doesn’t mean we should all the time.
Speed is a tool. Not the default operating mode.
Where This Opens the Door for ICs
Here’s the part that’s actually exciting.
Because while leaders are adjusting… this shift massively benefits individual contributors.
There are opportunities now that simply didn’t exist before.
You Can Operate Beyond Your “Role”
You’re no longer boxed in the same way.
A marketer can:
Analyze performance data
Draft strategy docs
Prototype messaging variations
An engineer can:
Write cleaner documentation
Explore product ideas
Communicate tradeoffs more effectively
A PM can:
Build rough prototypes
Validate ideas faster
Stress-test assumptions independently
The gap between idea and execution has shrunk.
You Can Anticipate Instead of React
This is where ICs really “step up.”
Before, work often looked like:
Task → Execution → Delivery
Now the best ICs are doing:
Context → Interpretation → Direction → Execution
Instead of waiting to be asked:
You bring options
You outline tradeoffs
You suggest timelines
You don’t just answer:
“When will this be done?”
You respond with:
“Here’s how I’d approach it, here are two paths, and here’s what each would take.”
That’s a different level of ownership.
You Can Multiply Your Impact Quietly
The ICs who stand out right now aren’t just using AI.
They’re using it to:
Reduce friction in their own work
Show up more prepared
Make better decisions faster
And importantly: they’re not announcing it every time.
They just look… sharper.
The New Unspoken Contract
If I had to sum it up, the dynamic now feels like this:
As a leader, I’m thinking:
“I know this is possible and help me understand the best way to get there.”
And the best ICs are thinking:
“I know I can do more than before and here’s how I’m going to make that count.”
The Bottom Line
AI didn’t just make work faster.
It changed how we relate to each other at work.
I don’t ask:
“Can you do this?”
Because I already believe you can.
But that puts more pressure on both of us to get the how right.
And if we do?
The ceiling on what a single person can accomplish just got a whole lot higher.
What do you think? Let me know in the comments!
Jake Smith
