Stop Asking for Time to Fix Technical Debt

Tech executives already know that security, testing, and reliability matter. The problem is timing. This work rarely rises to the top until an outage, breach, or missed deadline forces the issue. I have watched “we’ll handle it later” turn into a customer incident more times than I want to admit.

One reason it slips is language. Technical debt is a useful label, but it is easy to misinterpret. It can sound like vague cleanup, or worse, criticism of past choices: someone made a bad call, someone cut corners, someone didn't “do it right.” That framing invites defensiveness and obscures what leaders actually need to see.

Leaders don’t fund labels. They fund outcomes. So the move is to translate tech debt into decision-ready terms: delivery speed, operational risk, customer impact, and predictability.

Debt is Not the Enemy

Every organization has tech debt. It is often the cost of delivering value sooner and learning faster, both of which are rational business tradeoffs.

The enemy is letting that debt stay implicit until it turns into avoidable risk.

When you lead with outcomes, you are not asking for time to “fix code.” You are proposing a business improvement with a measurable return.

The Tech Debt Importance Filter

Not every backlog item is worth executive attention. Credibility comes from escalating the right ones and explaining them clearly.

Before you escalate an investment request, run it through this filter:

1. Blast radius: If this fails, is it a nuisance, or does it threaten revenue, reliability, or compliance?
2. Blocked capability: What can we not do today because of this? Ship more often, pass a security review, onboard engineers quickly, run safe experiments?
3. Business outcome: If we fix it, what metric improves that leadership already tracks? Time to market, uptime, support cost, churn, audit risk?
4. Compounding cost: Is this getting more expensive over time due to incidents, slower releases, or increased toil?

If you can’t answer these clearly, hold back. Handle the issues within your normal engineering prioritization.

Watch “Putting Tech Debt to Work”

I address these issues in my DjangoCon US 2025 Lightning Talk. My talk begins at the 3:34 mark:

If you want a quick way to apply this filter to your roadmap and current risk profile, contact us.