When You’re Unhappy With a Contractor’s Work…

…It sucks.

This might be the hardest part about managing independent contractors:  When you’re not satisfied with the work (or quality of work) they deliver.

On the surface, this seems like a relatively minor challenge.  Just demand a re-do.  Or just say screw-it and don’t hire them again after this.  Right?

Wrong.  It’s way more complicated than that (at least it is for me).

First, let me step back a bit.  I have been hiring and working with independent contractors, mostly fellow freelance designers and developers, for years.  I used to assemble mini-teams (me, another designer, and another developer) to scale up my client work.  Today, I regularly hire contractors to help out with various parts of Restaurant Engine.

I’ve seen my fair share of flakes.  You know them:  They don’t deliver what they promised on time, fail to communicate, and fail to deliver on basic requirements.  Those are the people I’d try once, then never work with again.  Luckily, over the years I have learned how to better evaluate contractors before hiring them…  But this post is not about these flaky types.

This post is about those contractors that have proven ability and are true professionals.  These are the guys and gals I continue to work with year in, year out, project after project.  They’re the talented ones, the ones who communicate and set expectations, and they’re the ones who charge deservedly higher rates than most.

This post is about those rare occasions when A-list contractors fail to deliver as they normally do.

I want to be the best client I can possibly be

This has been always been my number one goal since I started outsourcing to contractors.  I want them to know that when they work with me, I’m not like their other clients.  I want to be their best client.  The client they wish all of their other clients were like.  I want them to look forward to receiving an email from me requesting some new work, because they know, without a doubt, this project will be smooth-sailing no matter what.

Those who have worked with me know that…

  • I always provide detailed project specs, documented in a way that’s easy to follow.
  • I defer to the expertise of the contractor.  I’m hiring you because you do some thing better than I can.  I let you do what you do best and get out of the way.
  • I pay your invoices on time, every time.  Send me an invoice, and you can expect to be paid within 24 hours.  No questions asked.

Obviously, I know from first hand experience working with clients of my own how important these things are.

Why is this so important?

Two reasons:

First:  I strongly believe that when you enjoy working a person, and there’s a professional relationship built on trust, you deliver better work.  Period.  Budget has nothing to do with it.

In my experience working with my own clients, when I trust and enjoy working with someone, I actively look for ways to go above and beyond for them.  But when it’s a client that pays late, or always hassles and delays, it only leads to frustration.  With these clients, my attitude shifts to something closer to “I’m going to deliver what I promised, then move on.”

Second:  The competition for hiring the best designers and best developers is FIERCE.  And getting more intense year after year.

The best of the best are simply in such high demand — all year long — that it’s incredibly difficult to win a coveted spot in their project calendar.  So I try to do all that I can to get on that short list of people they’ll always try and make time for.

When things go wrong…

This doesn’t happen often.  It’s incredibly rare actually.  And that fact alone makes this even more difficult because it catches everyone off guard.

But everybody is prone to slip-ups.  Sometimes the developer didn’t take the time to fully test and troubleshoot some code before delivering.  Or a designer rushed through the process and delivered work that doesn’t live up to their portfolio.  Or they’re over-tired (from being so busy/in-demand) that they miss something.  Or they take an extra day or two past the promised delivery date.  These things happen.

It’s these moments and what happens next that separates the good contractors from the best contractors.

As a manager, when things go wrong, I get nervous.  I start questioning myself and what to do about it.

Do I confront them about the sub-par work they delivered?  Do I ask them to fix it?  Do we discuss how we can improve things moving forward?

Or do I stay silent?  Let it slide this time.  Hope they’re just having an “off” day and things will be better next time.

If I’m honest, it’s the latter option that I go with more often than not.  I fear upsetting the person, embarrassing them, or giving the impression that I don’t value their work.  I fear they will resent me for it.  And most of all, I fear this will chip away the excellent working relationship I worked so hard to maintain up until this point.

But I have also have gone with the first option — voicing my dissatisfaction — on a few select occasions.  And when I did, I was pleasantly surprised with the result and reminded of why I hired this rockstar in the first place, and why I stick with them.

The best of the best take constructive criticism well.  Instead of turning angry or combative, they ask questions. They do everything they can to see it from my perspective, understand what went wrong, and work with me to resolve it.  They don’t make excuses.  They see this simply as a hurdle that can be dealt with.

No biggy.



  • Bill

    I have seen a lot of shoddy contractors and the best way to deal with them is to make their lives miserable; turn them into the contractors licensing board, turn them into the better business bureau, make websites showing their horrible work, and then sue them for the cost of the cost of the whole job they have done and what it would cost to fix their crappy job.

  • Eve Grey

    I just hired a photographer to cover an event for a client. This guy was late to the gig, didn’t capture the photos that were the BIGGEST reason why the client wanted a photographer to begin with. The deadline was on a Monday for the photog to deliver the images to me then this contractor decides that he will hand over the images after I pay his balance on the invoice. I was given the opportunity to view them prior (watermarks are used, duh). Sad thing is he had me over a barrel and I needed photos that were delivered to me a week after deadline and none of them were of the most important part. Needless to say, I’m furious knowing that I paid this guy in full and didn’t get what I asked for. I will no longer do business with him, but it’s sad to know that these people exist.

    • Carol Thompson

      Hi Eve! I just read your comments about your very disappointed photography event. I have a photo club (Indianapolis, IN) and we are having discussions re watermarks, events, legalities, etc. I’m wondering if you instructed the hired photographer what you specifically wanted him/her to get first (a list of priorities), then other? I know that the post-processing (after the event) is usually what takes so long…and a lot of folks don’t realize that time should be factored into the cost. It’s rare (but desired) that a photo be perfect straight out of the camera. A lot of sports events have a high demand for turnaround…and those photographers have a very short turnaround time. So, did the photographer realize the time frame for turnaround? There was a photographer in our group a few years ago who would spend a ridiculous amount of time post-processing. It became rather irritating to me, to be honest! So…as our group moves forward trying to “learn how we can be better”, I wonder if you’d provide more information re this very disappointing event…so we can learn from it? cthomps4@live.com