Managing Contractors

Direct the outcome, not the method

The instinct with a new contractor is to manage them like a new employee: available, checked on, steered. Resist it, for two reasons.

The practical one is that you are paying for their judgement. A contractor who has built the thing before knows an order of operations you do not, and overriding it removes most of the value you are buying.

The other reason is classification. Directing how the work is done, setting hours and requiring attendance are exactly the factors that make a relationship look like employment, and the exposure from that lands on you.

What you should direct is what gets delivered, to what standard, and by when. That is not a lighter form of management. Done properly it is more demanding, because it requires you to have decided what you want.

Start well or spend the project catching up

Most contractor engagements that disappoint were decided in the first week. The contractor did not have the context, made reasonable assumptions in its absence, and delivered against those assumptions.

Front-load four things. The why, so they can make good decisions on the questions the brief did not anticipate. Access, on day one rather than day nine, since a contractor blocked waiting for a login is billing or losing time either way. The map, meaning who decides what, and who to ask when something is ambiguous. The constraints, including what cannot change and what has already been tried and rejected, which is the single most common thing clients forget to say.

Check-ins that are worth attending

A fixed rhythm beats an anxious one. Weekly is right for most engagements; twice weekly for short, fast projects.

Keep the agenda to three questions: what has been delivered against the scope, what is blocked and who owns unblocking it, and what has changed in what either side expected. That last one is where scope drift surfaces while it is still cheap.

What a check-in should not be is a progress report on activity. Hours spent and tasks touched are not what you are buying, and asking for them pulls you back toward directing the method.

Closing out

Projects rarely end. They fade, with a last delivery, a few loose questions, and an invoice somebody eventually chases. That costs you the two things worth having at the end.

Acceptance. Go through the acceptance criteria and record the outcome. If something is outstanding, name it and agree what happens rather than leaving it implied.

Handover. Whatever is needed to maintain the work without the contractor: credentials, documentation, decisions and their reasoning, and known limitations. Ask for the reasoning specifically. Six months later the question is never what was built, it is why it was built that way.

Then record what you would do differently, while it is fresh. Contractors are usually hired repeatedly, and the second engagement with the same person is far more productive if the first one ended with an honest note rather than a fade.