Most founders plan for money, but not for time. Here’s how timeline slip creeps in, what it costs you, and how to build smarter, more realistic roadmaps.
Everything takes longer. Ain’t that the truth, so here’s how to plan like you already know that.
A while back, I was reviewing a plan with a founder. They were sharp, prepared, and had all the right pieces in motion:
A fresh round of funding, a hiring roadmap, product milestones, investor updates—everything paced out over the next 18 months.
But when we got into the details, something stood out:
Every milestone lined up exactly where it was supposed to. No wiggle room. No delays. No slip.
“Looks great,” I said. “But what happens when things take longer?”
They hesitated. Blinked.
Then admitted:
“We haven’t really thought about that.”
They’re not alone.
Time is the quiet cost that sneaks up on you
Founders track capital with care—burn, runway, CAC, LTV.
But when it comes to time? It’s often an afterthought.
And yet, time is the thing you’re really burning every day. And unlike capital, you can’t go raise more of it.
Still, so many plans are built on the best-case version of a timeline:
- Hiring in 30 days
- Shipping a feature in 6 weeks
- Closing a round in 3 months
- Onboarding someone in 2 weeks
- Signing a big customer this quarter
That’s what the spreadsheet says. But that’s not what happens.
So what does happen?
You post a job. It takes 5 weeks to find the right candidate.
They accept, but can’t start for another month.
They ramp slowly. Meanwhile, the feature they’re supposed to own is blocked by a delay on another team.
That “quick” partnership? It gets caught in procurement hell.
That investor? They go quiet right before term sheet talks.
These aren’t rare edge cases.
This is just… what building actually looks like.
The real impact of slipping timelines
Missed timelines aren’t just schedule problems. They shake more than you think.
- Your team loses confidence in the plan
- Investors start asking tougher questions
- Metrics fall out of sync with your narrative
- You feel like you’re behind—even if you’re not
It’s not always visible. But it builds up. And if you don’t account for it early, you’ll start burning clarity along with your cash.
So, how do you plan for time?
Not in theory. In practice, I’d suggest to do this:
- Add slack, not fluff: Plan for the work and the waiting. Build in time for handoffs, learning curves, approvals, and regrouping. Things go slow before they go fast.
- Set ranges, not single points: Instead of “We’ll ship by May 1,” try “We’re targeting early May.” Then structure your communication and team expectations around that.
- Build for momentum, not velocity: Fast is good, but steady wins. A startup that moves consistently—even slowly—is better than one sprinting and stumbling.
- Track time as a resource: Just like cash. Track time-to-ship, time-to-hire, and time between decision and execution. You’ll see where things really lag.
5. Communicate openly when things shift.
You’re not late—you’re adjusting.
The faster you surface timeline changes, the more trust you earn.
It’s not about being slow. It’s about being honest.
Speed is part of startup culture. Everyone wants to move fast.
But speed without realism sets you up for misalignment—internally and externally.
You can build fast.
You should aim for urgency.
But your plan?
It should hold up even when the fast path breaks.
Because it will.
Here’s the part we forget:
You can raise more money.
You can replace team members.
You can rework your product.
But you can’t buy back lost time.
Plan like time is scarce—because it is.s.
Building your next roadmap?
Before you lock in the dates, zoom out. Add space. Ask what might take longer—and plan like it already has.
If you want a second set of eyes or just need someone to poke holes in the timeline, I’m around. Get in touch.