Stop Asking, "When Will That Be Done?"
How shifting this question changed my ability to deliver and lead teams
Most stakeholders and leaders ask:
“When will this be done?”
But the better question is:
“How much of this can we finish in the next period — week, month, or quarter?”
This one shift changes everything.
It flips the conversation from pressure and anxiety to planning and alignment. From blind guessing to clear collaboration. It invites iteration — and iteration is beautiful. It’s how great teams delight their customers on a regular basis.
📖 Story Time
The Website Refresh...
I was working with a team tasked with launching a new website. I still remember the first question the stakeholder asked after we finished our pitch:
“When will it be done?”
Fair question — they want to know when to market it, when value arrives, when to celebrate.
The problem?
Humans are terrible at estimating like that, especially across unknowns and moving parts.
So I reoriented their thinking:
“Let’s talk about how much of the website we can build in, say, the next month.”
That one question removed the assumption that “website” was a single, shared definition. (Spoiler: it never is.)
It invited clarity. The stakeholders were a little suspicious — but they leaned in.
This was the first time someone had reframed the work in a way that was both valuable and realistic.
And here’s how the team responded:
“In a month, we can build the new homepage with improved navigation and links to key pages.”
Boom. Now we’re having a real conversation.
No fake date. No missed expectations.
Just shared understanding.
In previous engagements, the team would’ve answered the “When” question with:
“Give us a month.”
A random, hopeful guess. A date we’d likely miss.
This new question flipped it — and gave the team power to speak with confidence about what they could deliver inside a meaningful timebox.
The Marketing Campaign...
I worked with a marketing team at Ramsey Solutions that was kicking off a new campaign.
The VP asked the classic question:
“When will the campaign be ready?”
But instead of forecasting the unknowable, I heard the team flip it to:
“How much of the campaign can we launch in the next two weeks?”
And just like that, the conversation shifted to real, deliverable value:
“We can publish the teaser video, draft the landing page, and run a soft launch to gather early engagement data.”
Boom again.
This created momentum.
Instead of guessing — they were delivering. Iteratively.
The awesome thing is, this question works for products, marketing, design, even operations.
Anywhere there’s work to be done and people asking “When?” — this is your better question.
🛬 Landing the Plane
In my experience, this approach works wonders — when it’s embraced.
At some companies, asking “How much can we finish in a set time?” was like speaking Latin to a deaf person.
The response:
“That sounds great, but we’re not ready for that yet.”
But here’s the truth:
We’re never “ready” until we start.
Time-boxing is how we begin.
Time-boxing is the secret sauce.
This kind of thinking teaches a powerful truth:
We own the time frame.
When I sign up for a race, I don’t ask:
“When will I be ready?”
I already know the race date — that’s when I must be ready.
Instead, I ask:
“How much training can I get in before that day?”
That empowers my plan.
The time frame shapes the strategy. And you can own the time frame!
Same with teams.
If we decide, “We’re launching something on the 21st,” we suddenly have direction.
We begin exploring the art of the possible — what we can deliver by then — instead of waiting for perfect or trying to assume when we will have all of it — whatever that even is.
Sure, sometimes the full website is the most important thing.
But if that’s the case, the date must remain flexible.
You should not have both a fixed due date and a fixed full body of work.
That’s not planning — that’s fantasy.
And it won’t deliver much of anything.
And that’s why companies exist — to deliver value to customers in ways that work for the business.
To deliver successfully, you have to choose what you’re optimizing for:
👉 The date?
👉 Or the scope?
Choose one. Shape the other.
Teach your stakeholders to ask the better question:
“How much can we deliver in this time period?”
Instead of:
“When will this be done?”
Until next time —
Keep Learning. Keep Growing.