Building a Freelance Team: Crafting The Interview

It’s fair to say that I’ve been comfortably outsourcing chunks of my workload over the past 1-2 years.  For a typical all-in website project (strategy, design, development), I might hire a designer or a developer (or both) and handle the remaining tasks myself.  It’s been working out well.  Sub-contracting has helped me take on more work and deliver better results.

But it’s taken me a long time to get to this point.  Hiring was very much a learning process in the beginning.  It still is today.  I find it very difficult to find and partner with freelancers who are great at what they do, but more importantly are consistently reliable.  Luckily, this past year I met and worked with a handful of rockstars in this regard.  I now consider them my “go-to” people for certain types of projects.  The one down-side of partnering with the best?  They get booked a lot!  So it’s time to expand my network of “go-to” freelancers so that I always have someone I can call when another is unavailable.

The hard part is determining who will become a “go-to” guy, and who will become a “one-and-done” hire.  You really can’t be sure until you complete at least one real project with them.  I’ve been surprised to find that some who have very impressive portfolios and high hourly rates still fail to deliver on simple—but crucial—things like meeting deadlines and communication.  But based on this experience, I can better my chances of finding a “go-to” guy by changing my initial approach.

Crafting a Freelancer Interview

In the past, I made the mistake of focusing too much on the immediate project at hand.  During those initial calls with the potential sub-contractor, I wanted to know whether or not this person can meet the requirements for this project.  Instead, I should have been focusing more on getting to know them.

So I’m crafting a new approach.

First, I’m doing the legwork during my downtime, when I don’t have an immediate need to hire someone.  This way I can focus more on whether or not the person will be a good fit for many projects to come.

Second, I’m spending more time than before reading job applicant’s emails, then digging through their portfolio, then reading their blog, their tweets, then re-reading their email response.  Many are easy to dismiss, but of the ones that are worth clicking through, I try to narrow those down to 5 or less.

Third, I’m taking the time to script a list of questions (shared below)—something I never did in the past.  I’ll probably tweak these questions even further to tailor it to the specific interviewee / position.

The Questions

I put a lot of thought into the questions listed below.  I thought about my past experiences working with sub-contractors, both good and bad.  Why did some guys work out while others didn’t?  For those that worked out well, what do they have that others don’t?  What kinds of questions will help me see those qualities?  For those that won’t be hired again, what went wrong?  What could I have asked that might have helped me foresee those issues?

One final tip on crafting questions for any type of interview (public or private):  Make them open-ended with room to elaborate.  Yes/no questions don’t do you any good.  The content of their answer is only part of what I’m evaluating.  I also want to gauge their communication skills:  Their ability to make me understand what it is they want to get across.

Here are the questions I came up with.

NOTE:  They’re geared for a web developer position since that’s who I’m looking for right now.  Most (not all) questions would apply when interviewing for another type of position.

WORK SITUATION

How long have you been self-employed?  What were you doing before that?

Do you work alone, have full-time partners, and/or outsource work?

Where do you do most of your work? (home, office, Starbucks…)

What are your typical working hours?

How do you prefer to communicate? (Email, Skype, GChat, or… gasp… telephone?)

What types of projects are you most interested in working on?

What types of clients do you typically work with? (designers, agencies, website/business owners, etc.)

Where do you want to take your business/situation in the next year?

THE NITTY-GRITTY

Mac or PC?

Which coding program do you use?

Rank your skills (specifics: PHP, HTML/CSS, JS, Rails, etc.) in order of expertise.  “Great at everything” is not acceptable.

Which CMS do you have the most experience with.  “All of them” is not acceptable.

Talk a bit about your biggest / most-notable project with said CMS, your role, etc.

Talk a bit about your process for a typical web development project, step-by-step.

PROJECT MANAGEMENT

How much advance notice do you need when accepting new projects?

Do you find yourself frequently turning down work due to lack of availability?  How do you handle these situations?

How many projects do you take on simultaneously?

What systems do you use to manage your workload?  (GTD apps, calendars, pen & paper, etc.)

How do you make sure your deadlines are consistently met?

That’s the work-in-progress template.  I’m interested to hear what you think…