How to tell what your software contractor is actually doing

You pay every month and you do not know what for. Not because anyone is deceiving you: the contractor's work lives in the contractor's tools, and what reaches you is a spoken summary once a month. That gap is normal, and it is also exactly where every misunderstanding is born. This is written so that you know what to ask for. It does not claim your contractor is bad, and it does not assume they are good.

Why you see nothing, even when everything is fine

The contractor has a task system, mail, conversations. The work happens there. You are in none of those places, so information reaches you through one person, the project manager, at the pace that person sets.

This works beautifully while things are calm, and breaks on the first day something goes wrong: precisely then that person is busy, and the last thing they do is write you a summary.

The conclusion is not «demand more reports». A report written by hand gets written when there is time, which is not when it is needed. What to ask for is access to what is recorded anyway.

Four questions before you sign

Ask them before the start, while answering is still comfortable.

• Who exactly will work on this. Not «a team of four», but names and share of time. A vague answer here turns, two months later, into «the developer who knew this has left».
• How will I know what has been done. The right answer is a place you can log into, not a promise of a monthly summary. If there is no such place, ask what there is, and note that the answer was «we will send it to you».
• What happens when a deadline slips. Not «we will not slip». Ask how you will learn about it, and when: on the day it happened, or at the end of the month.
• Who do I call when something is down. A name, not a role. And what happens when that person is on holiday.

Access you should hold from day one

This is not distrust, it is hygiene. Even with the best contractor in the world, these should be registered to you:

• The domain. Not to the contractor, not to one of their employees. It is the thing that hurts most to lose and cannot be taken back by force.
• Hosting and the server. At least an owner account you control, even if the contractor is the one maintaining it.
• The code repository. Holding the account where code lives does not require reading code.
• The system's mailbox. Letters to your customers go out of it, and replies come back to it.
• Third-party service accounts you pay for: payments, SMS, cloud.

The request is entirely legitimate and is not an insult. A professional contractor will sort it in an hour. A refusal, or repeated postponement, is itself the answer to «what happens if we part».

How to check an estimate without understanding the technology

You do not need to write code to ask three good questions.

«What parts is this estimate made of?» An estimate of «three weeks» that cannot be broken down is a guess. A breakdown into five items with numbers is an estimate, even if it turns out inaccurate.

«What is the riskiest thing here?» Every piece of work has one part that can explode. A contractor who says «there are no risks» either did not think, or does not want to say.

«What happens if it does not fit in time?» The answer that matters is not «it will», but what gets cut first. Agreeing the order of cuts in advance is worth more than any promise.

And a fourth question nobody asks: «what do you need from me, and by when?» Most estimates break not on code but on content, an approval or an access that did not arrive on time from your side.

What to ask for in the monthly report

A report that is one line with a total is not a report. What actually says something:

• Hours attached to tasks. Not «40 hours of development», but which task took how long. Without that you cannot ask «why did this cost so much», because there is nothing to point at.
• What closed and what opened this month. A «done» list on its own hides the main thing: how much new work joined the queue.
• What moved in the schedule, and why. Not a status of «in progress» that has not changed in three months.
• What cost money besides hours. Hosting, licences, external services. These accumulate quietly.
• What is stuck on your side. A good contractor will tell you they are waiting on you, and will say it before the month ends rather than in the report about it.

And ask for the report to arrive by itself, on a fixed date. A report that only comes when asked mostly measures whether you remembered to ask.

Warning signs, from mild to serious

None of them is proof on its own. Three at once is a conversation.

• The report only comes when you ask. The most common sign, and it is not about laziness but about the data not existing in a ready form. Those who have it send it unprompted.
• The report has hours and no tasks. «38 hours of maintenance» is not an answer, it is a heading.
• Tasks show no date of last movement. If you cannot see when something last moved, the contractor does not know either.
• «Why did it take so long» gets answered with «that is how it worked out». A real answer sounds different: «three reworks after the requirement changed on the twelfth».
• One person knows everything. Convenient right up to the day they fall ill. Ask who else knows, and ask for the answer in names.
• «We emailed you about it». Ask for a link to the letter. If the correspondence cannot be pointed at, the claim cannot be checked in either direction, including in the contractor's favour.
• Dates move silently. A date moving is a normal part of development. A date moving without anyone telling you is something else.
• «Almost done» repeats. A third «one more week» is not lateness, it is an absence of measurement.

What is not a warning sign

So that you do not look for an enemy where there is none.

• Silence in the chat is not idleness. Focused work looks exactly like that.
• Many hours are not necessarily good news. Sometimes it is a sign something was done twice.
• Swapping a person inside the team is normal. What is not normal is nobody telling you, and the knowledge not being handed over.
• «We did not manage it this month» is a legitimate answer when it is said on time and with a reason. A contractor who is never late usually just does not mention it.

Five questions once a month

Not an interrogation. A ten-minute conversation:

1. What closed this month, and which of it would I feel as a customer.
2. What opened this month that was not in the plan.
3. What is stuck, and with whom: you or me.
4. Which date moved, and for what reason.
5. What do I need to decide so that you are not blocked next week.

The fifth question matters more than the rest. A noticeable share of delays sits not with the contractor but in waiting for your answer, and both sides usually find that out too late.

What to do when it is already bad

If you have read this far and recognised three signs, the order of steps matters. And the right order is not «change contractor».

First, document a week. Not to accuse: memory usually exaggerates in both directions. A week of factual recording turns the conversation from «it feels like nobody is working» into «between the third and the tenth there was no update and two tasks did not move».

Then ask for a meeting with numbers rather than about feelings. Send the three questions you want answered in advance. A contractor who arrives prepared will answer; a contractor who arrives to explain why it is hard has already answered without answering.

Then ask for a thirty-day plan with two checkpoints in the middle. Not a promise, but points you can check along the way.

Only after that comes the conversation about parting, and the first question there is not «who do we move to» but «what has to move»: access, code, documentation, knowledge. A decent contractor will help; if they will not, it is good you found out now rather than in a year.

And one more thing, unpleasant but fair: sometimes the problem is not the contractor. If your side delays approvals, changes requirements halfway and asks verbally, nobody will look organised. The fifth question in the list above exists precisely for that.

What working transparency looks like

This is not a trade secret. Real transparency looks like this:

• there is one place you can log into and see the month: hours, tasks, what closed, what is open;
• every hour has a task it belongs to;
• every task has a date of last movement, and you can see it really moved;
• whatever was taken outside (a report, a file, an export) is recorded, with who and when;
• and whatever is stuck is visible without asking.

What that looks like in practice can be seen on the module pages, linked below.

And if your contractor has no such tool

That is not a reason to change contractor. Most of the above can be had with a shared spreadsheet and a regular meeting, if both sides genuinely maintain them. A tool does not create transparency; it only lowers its price, which is why transparency then survives a busy month.

What matters is the habit: a fixed date, the same structure every month, and data recorded as the work happens rather than assembled the evening before the meeting.

And if you are looking at tools anyway: we have one, and it answers exactly what is written here. But if your contractor works well without it, change nothing. This was written so that you know what to ask for, not so that you buy something.