What to ask your agency about technical debt

The version of this that works is simpler than the version most people imagine. If you are briefing an agency or a freelancer on technical debt, these questions are worth asking early.

The question is rarely whether something can be built, but what it costs to keep running afterwards. It is worth deciding this deliberately rather than inheriting whatever the last person set up.

Questions worth asking

• Who will actually do this work, and have they done it before?
• How will we know afterwards whether it worked?
• What happens if it needs changing in a year?
• What are you assuming that we have not confirmed?

What a good answer sounds like

Some debt is a deliberate trade, some is just neglect. It is worth being explicit about, because assumptions differ quietly. If it only works because one person remembers to do something, it does not work yet.

Paying a little down each cycle beats a rewrite. None of that requires a large budget, only a decision and someone to own it. Doing this properly once is usually cheaper than doing it approximately three times.

The short version

Most development decisions are really maintenance decisions wearing a different hat. Three things worth confirming about technical debt before you move on:

• Someone can say what the current setup is without going to look
• Track it in writing or it becomes invisible — and you know whether that is true here
• There is a way to tell whether the last change to this helped

If any of that sounds like a description of your current setup, it is fixable.