The Subcontractor I Trusted With No System

How I Thought It Would Work

I had more work than I could handle. A developer I knew was available. The arrangement seemed simple: she would do the implementation work, log her hours, send me a summary, and I would bill the client.

I did not set up a shared project. I did not give her access to any tracking system. I did not agree on how hours would be categorized. I just said, track your time and let me know.

For two months, this felt fine.

When It Stopped Feeling Fine

The client was a mid-sized e-commerce company. Good budget, clear requirements, friendly contact on their end. About eight weeks into the engagement they asked for a detailed breakdown of hours by task type.

Not unusual. Reasonable request.

I went to compile the report and realized I had two completely incompatible records. My hours were logged in Time-Trak, organized by project phase, with notes on each entry. Her hours were in a shared Google Doc, categorized differently, with some entries covering multiple days in a single line.

I spent an entire afternoon trying to merge and reconcile the two. I could not do it cleanly. The task categories did not match. Some of her entries overlapped with tasks I had also touched. Neither of us had logged meeting time consistently.

I sent the client the best version I could put together. They came back with questions I could not answer confidently. The relationship cooled after that. They did not renew.

What the Situation Actually Required

I needed one system, set up before the first hour was logged.

That meant getting my subcontractor into the same time tracker, under the same project structure, using the same categories I used for everything else. It meant agreeing on what counted as billable, what needed a note, and how to handle time that touched multiple tasks.

None of that takes long to set up. It just has to happen before work starts, not after a client asks a hard question.

The Part I Had Not Thought About

When two people work on a project and track separately, you end up with two different stories about the same work. Neither story is necessarily wrong. But they are hard to reconcile under pressure, and clients notice when your report feels stitched together.

The other thing I had not thought about: if the client ever questions the hours, you need to be able to speak to every line. When your subcontractor logs a four-hour block labeled misc development, you cannot defend that entry in a client meeting. You were not there. You do not know what misc development means.

Detailed entries with clear notes protect everyone. But you can only require that if you set the expectation up front.

What I Do Now

Every subcontractor I work with gets added to the project in Time-Trak before they log a single hour. We agree on how tasks are named. I ask for notes on anything over an hour. And I do a quick review of their entries every Friday so I am never surprised when invoice time comes.

This takes about thirty minutes to set up at the start of a project and maybe ten minutes a week to maintain. That is nothing compared to the afternoon I wasted trying to reconcile two incompatible time logs while a client waited.

The Lesson Was Not About the Subcontractor

She tracked her hours honestly. The hours were probably accurate. The problem was entirely structural, and it was entirely mine to create or avoid.

If you bring in outside help, the time tracking system is part of the onboarding. Same tracker, same project, same categories. Anything else is just hoping the two records happen to line up when someone asks a hard question.

Sometimes they will. Often they will not. And you will find out at the worst possible moment.

Track your time, bill every minute.

Time-Trak is a native Mac and Windows time tracker with a floating timer, automatic screenshots, and one-click invoicing.

Free during beta.

macOS + Windows · Floating widget · Auto screenshots