“This will take us about three months.”

I look across the table. “What would it take to ship something in two weeks?”

Silence. Then nervous laughter. Then, every single time, someone says: “Well, if we just…”

That moment. That’s where everything changes.

Comfort Is the Default Setting

Most people aren’t comfortable moving fast. The default mode, both in life and business, is to move without pressure. It feels safe. Predictable. Controlled.

But safety is often the enemy of progress.

People don’t resist speed because it’s impossible. They resist it because it’s uncomfortable. Speed introduces pressure, and pressure reveals weak thinking, vague planning, and slow decision-making.

In most companies, “a quarter” becomes a shield. It gives people time to stay busy without producing breakthroughs.

High-performing teams don’t wait for the perfect plan. They move, learn, and adjust.

Speed Is a Culture Test

How people react to speed tells you everything about your culture.

Some get anxious; they fear being exposed. Others get excited; they see a challenge worth tackling.

The ones who light up when asked to move faster are your multipliers. They thrive on clarity, urgency, and forward motion. Build around them.

What Speed Actually Reveals

Speed is uncomfortable because it exposes reality. You can’t hide behind long timelines, endless meetings, or vague plans. And that’s precisely why it works.

When you compress time, three things happen:

1. You force real decisions. No more “let’s discuss this next week.” You have to choose now, and live with the choice long enough to learn from it.
2. You reveal clarity gaps. Vague goals that could hide in a quarterly plan become instantly obvious when you have 14 days. “Improve the user experience” means nothing. “Get 20 customers to complete the new checkout flow” means everything.
3. You expose competence. The people who can operate at speed aren’t necessarily smarter; they’re just clearer thinkers who know how to separate what matters from what doesn’t.

Moving fast doesn’t mean being careless. It means cutting friction. Speed comes from short feedback loops, fewer approval layers, clear ownership, and a bias toward action.

Instead of waiting to “perfect” something, create a prototype of progress, a small, testable version that gets real feedback fast.

The Two-Week Question in Action

A product team once told me their new feature needed 12 weeks. “We have to interview users, design the flow, build the backend, test everything…”

I asked the two-week question.

They shipped a working prototype in 11 days. It was scrappy, a manually-triggered backend, a basic UI, zero polish. But it was real. Customers could use it.

The feedback changed their entire approach. Two of their core assumptions were wrong. They would have spent 12 weeks building the wrong thing.

The two-week question forces focus. It strips away everything nonessential and spotlights what truly matters:

• What can we test right now?
• What would “done” look like in 14 days?
• What’s blocking us from learning faster?

You’ll discover that most “impossible” goals just suffer from lazy timelines.

When to Ignore This Advice

Here’s what I’m not saying: that every project should take two weeks, or that careful work is worthless.

Sometimes “this will take a quarter” is actually right. The person knows something you don’t about technical dependencies, regulatory requirements, or market timing. Some things genuinely need to bake.

The question is: how do you tell the difference between legitimate complexity and padded timelines?

Ask for the dependency chain. “Walk me through what has to happen in sequence.” If it’s real, they can map it. If it’s padding, they’ll talk in circles.

Then ask: “What could we learn in two weeks that would change our approach?” Even in a legitimately long project, there’s usually some early signal you can chase.

The “Kick-Ass” Filter

Fast environments aren’t for everyone, and that’s okay. Some roles genuinely require deliberation, legal review, safety-critical systems, and deep research. Even speed demons need recovery periods.

But most work deserves more speed than it gets.

And for the right people, speed is fun. It’s a game of creativity, constraint, and impact. The ones who love it, the kick-ass players, will always figure out how to do it faster, better, leaner.

They don’t just survive in speed; they come alive in it.

What to Do Monday Morning

Find one project with a “realistic” timeline on your calendar. Ask the two-week question.

Don’t commit to the answer yet. Don’t promise anything to anyone. Just notice what the question reveals.

Notice who gets defensive. Notice who gets energized. Notice what assumptions crumble when you apply pressure.

Because progress loves speed, and speed loves people who care enough to move.

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Bottom line: Bias for action + moving fast + clarity of thinking = Unstoppable