Written by Daria Turanska
I run a legal document business with no employees and one contracted developer. That arrangement has forced me to be far more deliberate about delegation than I ever was when I managed a team, because every handover costs money I can see.
The decision that shaped everything was not who to bring in. It was what I would not give up.
I kept the drafting. At FasterDraft (https://fasterdraft.com) the templates are the product, and the judgment about what a clause should say, and which clause a given user needs, is the thing customers are actually paying for. I gave away the code, which is essential, difficult, and not what anyone is buying. That split looks obvious written down. It is not obvious at the time, because the work you want to offload is usually the work you are worst at and most frustrated by, and that is a different question from what is safe to offload.
The rule I would offer is that the first thing you delegate should be the thing where you can judge the output but cannot produce it efficiently yourself. I can tell whether a page loads, whether a checkout completes, whether a fix held. I could not build any of it at a sensible speed. That is a good candidate. Work where you cannot assess quality without doing it yourself is a bad candidate, no matter how much you dislike it.
Earlier in my career I supervised a legal team spread across several countries. The thing that made that hard was never the timezones, which people fixate on. It was decision rights. When it was unclear who could approve something, work would sit, and the person waiting would usually assume someone else was handling it. Distributed teams do not fail because people are asleep at different hours. They fail because ambiguity has more room to hide when nobody shares a corridor.
That translates directly to contractors, and more sharply, because a contractor has no incentive to absorb your ambiguity. An employee who receives an unclear instruction will often chase it down, because they will still be there next month living with the consequences. A contractor will reasonably build what the brief said, invoice, and move on. Vague scoping is therefore not a minor irritation in a contracting relationship. It is the main failure mode.
There is a legal layer to this that small businesses skip, and I would not skip it even though it is my own field and therefore the boring part of my day.
In the US, worker classification is the one to get right, because the tests for independent contractor status differ by state and the consequences of getting it wrong are retrospective. The UK has its own version in the off-payroll rules, and Australia has been tightening its definitions too. If you engage the same person full time, direct how they work, and give them no real independence, calling the arrangement contracting in the paperwork does not make it contracting in the eyes of the relevant authority.
The clause that matters most is the one nobody negotiates: intellectual property assignment. In the US, work created by a contractor does not automatically belong to the business that paid for it. Without an express written assignment, you can find that you have paid in full for code, designs or content you do not own. This is not an exotic scenario. It is the default position, and it surfaces at the worst possible moment, typically during due diligence or a dispute.
Cross-border adds a third question that people leave until last: which country’s law governs the agreement, and where a dispute would actually be heard. Getting a favourable governing law clause is of limited comfort if enforcing it means litigating somewhere you will never realistically go.
The version of this I would put to anyone building a small team: write down the two or three things that only you can do, in specific terms rather than as a job title. Everything not on that list is a candidate for someone else. Then spend real time on the scope of the first engagement, because the brief is the management system. With a contractor, there is no corridor, no overhearing, no picking things up by proximity. There is what you wrote down.
The work you protect defines the business. Everything else is a purchasing decision.
Author Bio: Daria Turanska is the Legal Manager at FasterDraft.
