I Planned the Perfect Sprint...It Still Fell Apart

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Alright, let’s get into this week’s lesson, one that started with a sprint plan I was sure was airtight.

A well-written spec doesn’t guarantee a well-run sprint.

It’s not the plan that matters most. It’s the shared understanding behind it

📖 What Happened:

In my second month at HubSpot, I finally felt like I had my footing.

My two engineers and I were taking on a new piece of a reporting migration: no designer, no dependencies, just us. I wanted to do it right.

So I built the cleanest planning doc I’d ever made:

• Clear goals

• Edge cases considered

• Jira tickets linked

• Shared async, then walked through it live

It felt like I’d hit my stride.
Until we actually started building.

Our standups all sounded “on track,” but Jira told a different story.
Tickets were stuck. Work was misaligned.
We were reading the same doc, but drawing different conclusions.

And that’s when it hit me:
The spec wasn’t the problem. The process was.

🛠️ What I Do Now (and Why It Works):

I stopped treating the planning doc as a finished product.
Now I treat it as a collaborative artifact that evolves as we go.

Here’s the framework that helps:

1. Align
   Before anything gets documented, we align on the problem and context. Even a 15-minute chat helps avoid costly misunderstandings later.

2. Co-write
   I’ll rough out the outline, then tag in others. My TL reviews async. Design drops in early mocks. It’s no longer my doc, it’s our plan.

3. Reality Check
   We sanity-check the scope: What feels unclear? What might blow up? Are we being too optimistic?

4. Re-align
   Once the sprint starts, we treat the plan like a living thing. Check-ins. Show & tells. Quick recalibrations.

We stay aligned, not because we nailed the plan upfront, but because we keep updating our understanding together.

🧪 The Litmus Test

Ask yourself:

• Did I write this alone?

• Has the doc changed since kickoff?

• Are we still referring to it mid-sprint?

If the answer to any of those is “yes,” there’s a good chance your plan won’t stick.

📚 Want to Dig Deeper?

Here are a few excellent reads on this topic:

• Are roadmaps ever useful?

• How to Write a Good PRD

• The Planning Fallacy

👋 Before You Go

If you found this helpful, I’d love for you to do two things:

1. Subscribe to Stef the PM for more lessons like this (and the occasional template drop) → Subscribe here

2. Refer a teammate and unlock my actual planning doc template when you do →

Thanks for reading.
See you next Friday.

- Stef