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The Urgent Ask
Imagine this: you’re leading engineering at a startup and halfway through a planned sprint a colleague barges in with a time-sensitive opportunity.
Our Head of Supply came to me with partnership that had to happen now. This work involved integrating with a new platform immediately - an effort not on our roadmap for this quarter, with unclear ROI, and zero spare engineers to throw at it.
The market window was narrow, and the pressure to act quickly was intense.
It was one of those moments in startup life where you feel torn: stick to the plan, or grab the opportunity and scramble.
The Trade-offs
As Head of Engineering, I was stuck at the intersection of urgency and reality.
On one side, we had our commitments and a team already at full capacity.
On the other, a fleeting opportunity dangled by our Head of Supply.
We brainstormed a few paths, none of them painless:
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Pull a developer off an ongoing project to tackle the integration, accepting that their original project would slow down
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Ask our CTO to roll up his sleeves and spearhead the integration (as if he wasn’t busy enough)
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Defer the project, risking that the partnership might evaporate if we waited.
Each option had consequences. Reassigning a dev meant disrupting another team’s progress. Leaning on the CTO could only stretch him thinner. And deferring? That meant possibly missing the boat entirely.
In a larger organization we might debate this for weeks, but startup time moves faster.
We had to make a call by the end of the week. Tomorrow.
Decision and Disruption
In the end, I green-lit the integration by moving one developer from an unrelated product feature onto this project.
To soften the blow, I realigned priorities across three other squads, effectively creating a temporary task force around the integration.
Yes, it caused a bit of chaos - roadmaps were adjusted on the fly - but we avoided outright rebellion.
The developer was excited (who doesn’t like a fresh challenge?), and the other teams took the change in stride with only mild grumbling.
We managed to show urgency without (visibly) frustrating everyone.
However, I later learned one squad felt caught off guard. In the rush, I’d failed to personally brief that team’s developers before the shuffle was announced.
Hearing this feedback stung.
As much as the decision made sense, my communication fell short. A well-intended move can still leave people feeling sidelined if not handled openly.
Closing Thoughts
This experience highlighted the emotional and practical tension in startup decision-making. We pride ourselves on planning and process, but in a startup, speed and adaptability often outweigh process purity.
Industry wisdom often preaches thoughtful, data-driven choices - Ray Dalio, in Principles, emphasizes an idea meritocracy where decisions are weighted by the credibility of those giving input.
In theory, I’d gather my team’s best minds, weigh their experiences, and come to a believability-weighted consensus.
But when a narrow window opens, you sometimes have to act first and analyze later.
At a certain point, even a measured approach must give way to decisive action when things are evolving fast.
That urgency doesn’t excuse skipping communication, though - a lesson I learned the hard way - we work with people, not just processes.
In the end, 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.
Our integration gamble maybe will pay off in results, but it also reminded me that how we execute decisions matters as much as what we decide.
Next time, I’ll strive to keep the speed without leaving my team in the dark. While agility is key, trust and transparency are what truly carry a team through the chaos.