Halfway through a planned sprint, our Head of Supply walked into my office with a time-sensitive opportunity.
A partnership that had to happen now. Integrating with a new platform - not on our roadmap for the quarter, unclear ROI and zero spare engineers to throw at it. The market window was narrow. The pressure to act was intense.
One of those startup moments where you’re torn. Stick to the plan or grab the opportunity and scramble.
Table of contents
Open Table of contents
The trade-offs
I was stuck at the intersection of urgency and reality.
On one side, the team had commitments and was already at full capacity. On the other, a fleeting opportunity dangled by the Head of Supply.
We talked through a few paths. None of them painless.
- Pull a developer off an ongoing project to tackle the integration. Accept that their original project slows down.
- Ask the CTO to roll up his sleeves and spearhead the integration, as if he wasn’t busy enough.
- Defer the project and risk the partnership evaporating.
Each had consequences. Reassigning a dev disrupts another team’s progress. Leaning on the CTO stretches him thinner. Deferring means potentially missing the window.
In a larger organization we might debate this for weeks. Startup time is shorter. The call had to land by the next day.
The decision and the disruption
I green-lit the integration by moving one developer from an unrelated product feature.
To soften the blow, I realigned priorities across three other squads, effectively creating a temporary task force around the integration.
It caused chaos - roadmaps adjusted on the fly - but we avoided open rebellion. The developer was excited - a fresh challenge helps. The other teams took it in stride with mild grumbling.
Urgency without visible frustration.
Then I learned one squad felt caught off guard. In the rush, I hadn’t personally briefed that team’s developers before the shuffle was announced. That feedback stung. The decision made sense. The communication didn’t.
A well-intended move can still leave people feeling sidelined if it isn’t handled openly.
Closing thoughts
This surfaced the tension at the heart of startup decision-making. We pride ourselves on planning and process. In practice, speed and adaptability often outweigh process purity.
Industry wisdom leans toward thoughtful, data-driven choices. Ray Dalio writes about an idea meritocracy where decisions are weighted by the credibility of those giving input. In theory, I’d gather the best minds, weigh their experience and come to a believability-weighted consensus.
When a narrow window opens, you sometimes have to act first and analyze later. Even a measured approach gives way to decisive action when things move fast.
Urgency doesn’t excuse skipping communication. That’s the lesson. We work with people, not just processes.
Startup leadership often comes down to choosing the least terrible of several imperfect options. You make the best call you can, as fast as you can and you try to minimize collateral damage.
The integration gamble may pay off in results. It also reminded me that how we execute decisions matters as much as what we decide.
Next time, I’ll keep the speed without leaving my team in the dark. Agility is part of it. Trust and transparency are what actually carry a team through the chaos.