The framework every founder should use to hire contractors

Startup founders often hire contractors to get projects done faster without expanding their in-house team. Contractors help keep the company lean while delivering value to users — momentum is very important to any startup. But as with regular hiring, finding the right contractor is a huge challenge. Hiring the wrong person or team can slow your company down. You need to detect bad contractors and shady teams early on.

We've built a framework to better qualify contractors. It will save your time, money and help avoid stories like this:

  • contractor worked 7 hours a day on his own startup and was cheating with UpWork time tracking
  • an outsourcing company creates a product with a lot of bugs and terrible UX and the startup almost lost two enterprise customers who committed to try it at the idea stage
  • an idealist engineer trying to rewrite the whole product from scratch, without understanding current state of things

1. Start with a short-term test project

Once you found a suitable candidate — don't rush to assign them a large multi-month project. Start with small task or project that takes from a few weeks up to 1 month.

  • set clear goals and deadlines for your project, write down and share agreements
  • create a sense of urgency, tell why getting things done fast is important for your product
  • ask upfront what they need to complete their work, make sure to resolve any blockers

2. Monitor the progress and iterate

It's important to see if contractor can work independently and get things done. You should not micromanage, but check in often:

  • ask to publish progress and plans daily
  • meet at least few times a week to review their progress and see how it matches with daily updates
  • provide clear actionable feedback and check if it’s fixed
  • be friendly, but don’t build close relationships before or during the trial phase

Iterate on few projects/tasks before reducing the amount of time you spend to review work and follow up.

3. Decide on long-term hire

Ask these questions to make final decision on the hire:

  • did they provide enough value for your company? what are the things they’ve completed?
  • are they excited about your product and share your company values?
  • do they fit your team well?

In case of single ‘no’ — provide feedback and re-iterate. In case of two or more ‘nos’ — fire the person and start over. Usually two weeks should be enough for the first assessment.

4. Onboard contractors once you validated them on a short project

The best founders I’ve seen care about their team as they would care about their family.

  • make them feel like part of your team, so they know they’re as important as your in house team, earn their trust
  • share your company vision and roadmap every month
  • if things work well, consider proposing some equity to keep them long term


To recap, to you hire great contractors with less risks — start with a short-term project, see how they work with minimum guidance from your side and how they reflect feedback, iterate multiple times to ensure they bring value to your product, onboard them and give transparency once you’re ready to switch to a long-term agreement.

Written by Andrew Orsich and Igor Krasnik. Thanks for John McTavish and Vitaliy Bychik for reading drafts of this.