Your kickoff is the problem

Everyone can ship now. So why are we still building the wrong things?

I had a conversation recently with someone who told me their team spent three weeks shipping something that should have taken a few days.

No big surprises. No crazy scope. Just a straightforward feature.

Three weeks.

And I remember thinking… yeah, that sounds about right.

Because I’ve seen that exact situation play out more times than I can count.

It usually starts the same way. You get everyone in a room. Smart people. Product, design, engineering. There’s energy. There are ideas. It feels like progress. Everyone leaves thinking, “cool, we’re aligned.”

Except you’re not.

You’re just agreeing to keep talking.

Then a few days later, things start to slip.

Engineering raises a constraint no one mentioned in the kickoff. Design starts drifting in a slightly different direction. Scope quietly expands because “it would be nice if we also…”

And now you’re fucked.

Decisions don’t happen in the room anymore. They happen in side conversations. Slack threads. Quick huddles where half the context is missing.

And by the time something ships, it’s technically done… but it’s not what anyone thought they were building at the start.

I’ve been in that loop more times than I can count.

For a long time, I thought this was a design problem. Or a communication problem. Or just a symptom of moving fast.

It’s not.

It’s a kickoff problem.

More specifically, it’s a decision problem.

Most kickoffs are just expensive brainstorming sessions.

Nobody actually decides anything. You just explore ideas and call it alignment so everyone can feel good walking out of the room.

The teams that consistently ship things that convert do something very different.

They make the hard calls early.

They force constraints before ideas have a chance to multiply and spiral.

They get painfully clear on a few things right away.

What are we actually solving?​
​What are we explicitly not solving?​
​How much time do we really have?​
​What tradeoffs are we willing to accept?

That’s it.

No frameworks. No bullshit. Just decisions.

If you get that right, everything downstream gets easier.

If you don’t, you spend the next three weeks paying for it in rework, confusion, and slow delivery.

I got tired of watching good teams burn time on this, so I stripped my kickoff down to the minimum that actually forces clarity.

No decks. No long workshops. No over-engineered process.

Just a simple structure that forces the room to make real decisions before anything gets built.

If you’ve got a kickoff coming up, I’d try running this 10-minute kickoff before the meeting ends and see what changes.

Worst case, nothing changes.

Best case, you stop wasting weeks building the wrong thing.

And if you record your sessions, I’ve also been turning those conversations into a first draft PRD using this tool.

It’s not perfect, but it saves a shit ton of time getting something structured that engineering can actually react to.

Curious how your team runs kickoffs right now.

Hit reply and tell me how your last kickoff actually went. Was it clear, or did it turn into chaos?

Featured this week

You lose your job. No warning. Or maybe you felt it coming.

That moment where it hits you… “what the hell do I do now?”

We talked about what actually happens in those first few days after getting laid off as a product designer, and what it really takes to get back on your feet in the current market.

Not theory. Not generic advice. Just what we’ve seen work (and fail) firsthand.

You can watch the episode here.

Till next week,