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Solo and Small Firm Practice

Delegating to Independent Contractors

By Sam Glover

Recently I wrote that delegating to employees is essential if you want to build a business. But modern solo and small law firms often use independent contractors as well. Working with independent contractors is similar to working with employees in some ways, but different enough to merit its own post.

Work With Independent Contractors Who Share Your Core Values

Before you delegate anything to an independent contractor, make sure you are working with the right one. This means ensuring they have the requisite range of skills and knowledge for the task at hand, of course. But also, just as you want to hire and manage employees based on your firm’s values, you should seek to work with independent contractors who share those values.

Your firm’s values are like a core set of expectations that apply to everything you do. So if you and your independent contractor share values, it will be much easier to set expectations and get on the same page at the beginning of a project or task. Of course, this is more important with contractors who you hope to have a long working relationship with, or who will be working on client matters. But it’s worth looking for contractors who share your values as a general rule.

Set Expectations for the Work

Just as with an employee, you must start your relationship with an independent contractor by setting expectations. If you are posting a request for a proposal to a freelance marketplace, for example, make sure the posting contains a good description of your intended outcome. If there is a deadline, include it along with a time estimate. For example:

  • Not great. “I need help drafting a response to a motion for summary judgment in Ohio state district court.”
  • Much better. “I need someone to help me draft a response to a motion for summary judgment in an employment discrimination lawsuit in Ohio state district court. Work and deadlines are as follows: (1) Research memo due on February 1, followed by a strategy discussion to roadmap the brief. (2) Write the first draft of the brief, due on February 15. (3) After I mark up your draft, revise the version, copyedit and format it for submission between February 20 and 25. The brief is due on February 28. I expect this project to take approximately 30 hours, total.”

You could also include a link to your firm’s core values statement. (If you haven’t taken the time to write them out, that’s something you should definitely do.)

When you interview candidates, or start a new project with a contractor you already have a relationship with, take the opportunity to add important context, like strategic considerations that will help your contractor understand the big picture. Make sure they know what additional resources are available to them, such as your legal research platform.

As with an employee, always state the obvious. Just because something is obvious to you doesn’t mean it will be obvious to your contractor. Make it clear to minimize mistakes.

Check In Regularly

You should have a short weekly check-in with your independent contractor while the project is underway to maintain communication and momentum. When you check in, focus on three things:

  1. What they have done so far — and what you have done, if you are also working on the project.
  2. What they (and you) will do over the next week.
  3. What obstacles are standing in their way, so you can help remove them.

Aim to keep your check-ins to about 10 minutes or less. The goal is to maintain momentum and remove obstacles, not suck up valuable time with meetings.

Give Feedback Early and Often

An independent contractor can only fix problems if they know about them. If they are doing a good job, tell them to keep up the good work. If the project has gone off the rails, work together to figure out how to get it back on track.

And at the end of the project, make sure they know how it went from your perspective.

Be constructive, of course. Start with positive feedback, then make a gentle transition to what needs improvement. Approach problems as an opportunity for improvement for everyone rather than worrying about who is to blame.

A reliable independent contractor can be an essential teammate in serving your clients when you are swamped or need to rent someone’s expertise. Setting expectations, maintaining communication and giving constructive feedback should help you get there.

Related Posts on Attorney at Work

“Delegating to Junior Employees” by Sam Glover

Outsourcing for Ethics Compliance” by Megan Zavieh

“Rethinking Your Community” by Megan Zavieh

Outsourcing: When You Can’t Clone Yourself” by Kristin Tyler

“Smart Growth: Tapping Into the Freelance Lawyer Ecosystem” by Dan Lear

“Lawyers’ Struggle for Work-Life Balance: Running Your Business” by Dustin Cole

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Sam Glover Sam Glover

Sam Glover is the founder of, an online place for lawyers to learn how to start, manage and grow a modern law practice, and home to a community of innovative lawyers building the future of law. Sam is a former plaintiffs’ lawyer and ABA Journal Legal Rebels Trailblazer. Follow him @samglover.

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