---
title: Navigating High-Stakes Feature Delivery Amidst Infrastructure Instability by Quantifying Risk and Presenting Strategic Options
created: 2026-03-25
updated: 2026-03-25
type: summary
tags: ["delivery", "notes", "risk", "strategy", "telegram"]
external: http://go/ui/posts/2262/
---

Here’s a strong, structured answer you can adapt to your own experience:

The Answer
“This is a situation I’ve navigated before, and my approach is to reframe it — not as ‘delivery vs stability’ but as ‘what does delivery actually cost us right now.’”

The situation:
At my previous company, we were mid-way through a major infrastructure migration — moving from a monolithic deployment to a Kubernetes-based setup. Halfway through the quarter, leadership came to the team with a hard commitment they’d made to a key enterprise client: a new feature had to ship by end of quarter, no negotiation. The problem was our deployment pipeline was in a half-migrated state — we had no reliable rollback mechanism, observability was patchy, and we’d already had two production incidents that month.

What I did:
My first instinct wasn’t to push back in the room — it was to make the risk legible. Engineers often say “this is risky” and leaders hear “engineers being cautious again.” So I spent a day building a concrete picture: I documented our two recent incidents, their blast radius, and how long recovery took. I then modelled what a third incident during the delivery crunch would look like — not in technical terms, but in business terms. Customer impact, SLA breach exposure, engineering hours lost to firefighting instead of feature work. I called it a “stability tax” — every hour we spent fighting fires was an hour not spent on the feature itself.
I then went to my engineering director one-on-one before any group discussion. I didn’t go in saying “we can’t do this.” I went in saying: “I want to make sure we hit this deadline — here’s what I think puts that at risk, and here are three options for how we proceed.”
The three options were:
	1.	Ship as planned, accept the risk, but set up an on-call war room and have an incident response plan ready
	2.	Descope two non-critical parts of the feature to buy us one week to harden the pipeline first
	3.	Negotiate a two-week extension with the client, framed as “ensuring quality at delivery” rather than a slip

The outcome:
Leadership chose a hybrid of options 1 and 2. We descoped one piece, hardened the most critical part of our pipeline, and shipped on time. We had one minor incident during the crunch — because we’d prepared for it, we recovered in 40 minutes instead of what could have been hours. The client was happy. More importantly, my director later told me that framing it as options rather than a blocker was what made the conversation productive instead of adversarial.

Why This Answer Works
It shows you lead with data, not opinion. Saying “I think this is risky” is easy to dismiss. Showing the business cost of the last two incidents is not.
It demonstrates you understand leadership’s position. You didn’t go in to win an argument — you went in to solve a shared problem. That’s what Canva’s leadership competency is actually testing.
The “three options” move is powerful. It shifts the dynamic from you being an obstacle to you being a strategic partner. Leadership gets to choose — they just choose from options you’ve already validated as reasonable.
You own the outcome either way. If they pick the riskiest path, you’ve documented the risk, prepared for the incident, and you’re not blindsided. That’s maturity.

One Sentence to Open With
If you want a strong opener that signals confidence immediately:
“My instinct in that situation is never to say no — it’s to make the true cost of yes visible, and then give leadership real options to choose from.”
That single line tells the interviewer you’re collaborative, commercially aware, and not someone who hides behind process. Land that first, then walk through your story.​​​​​​​​​​​​​​​​
