Hiring an outside contractor can be a great solution when your startup requires specific skills or needs short-term, specialized help. That's especially true when you're bootstrapping. For example, if you need a logo, you certainly wouldn't interview and hire a full-time designer.

Deciding you want to hire a freelancer or contractor can be fairly easy, though. Hiring the right contractor can be a lot tougher. Definitely, check out qualifications, speak to references, and evaluate past work. And then look for more subtle signs that a particular contractor is right for you.  

1. Great contractors don't underestimate complexity or overpromise results.

Even small projects can create ripple effects that impact other areas of an organization. Major projects can be extremely disruptive, especially because changes often result.  

A contractor that plays down the disruption factor is either too inexperienced to understand the changes that will occur or is trying to skip past those details in order to win your business. And a contractor that promises the stars when all you need is the moon? When something sounds too good to be true, it usually is.

Great contractors tell you the truth. Great contractors don't underestimate potential downsides and don't overpromise.

Although they often over-deliver.

2. Great contractors don't pretend to have all the answers.

Granted, the contractor's job is to provide answers. But some answers you'll develop together; after all, who knows your business better than you?

Look for a contractor willing to be cooperative and collaborative. One size doesn't fit all, especially where your business is concerned.

3. Great contractors excel at the hand-off stage.

Some solutions are turn-key. Most are not, though. Sometimes a little training is involved, sometimes a small amount of customization, sometimes implementation doesn't go seamlessly...

Great contractors work with you until everything is running smoothly. Make sure "turn-key" doesn't mean "hands-off" where implementation is concerned.

4. Great contractors make themselves obsolete.

Although there are situations where hiring a contractor for a long-term engagement makes sense, typically you hire a contractor because you need short-term help.

A great consultant doesn't try to set up shop in your facility. Think twice about a contractor unwilling to train your employees, or to provide a solution you can implement on your own, or to provide services that don't require continual "maintenance."

5. Great contractors love to talk about the details ahead of time.

While it doesn't happen often, unfortunately, some contractors intentionally keep requirements and expectations relatively fuzzy - that way they can add additional scope to the project (or find reasons to increase the price.)

Great consultants want to know exactly what you need and expect. That way they can deliver what you need and expect.  While that takes more time up front... the benefits on the back end are worth it.

6. Great contractors don't try to sell you things you don't need.

Do you try to sell your customers things they don't need? Of course not. Your goal is to build trusting relationships and create long-term customers.

Those are also the goals of a great contractor.

7. Great contractors listen -- especially to you.

What you want, and what your employees want, can often be two very different things. You may only be able to afford a limited solution, while your employees might have a laundry list of features they want a product or service to deliver.

Great contractors listen to everyone, and then make sure that you, the owner, make the final call.

And they let you know what employees want so you can manage those expectations ahead of time.  

8. Great contractors are willing to say no.

A can-do attitude is great, but sometimes the impossible, especially for a certain price, really is impossible. Yet some contractors will say "yes" to almost anything just to get the gig and the revenue.

(Granted, sometimes a specific contractor may have an unusual, even groundbreaking solution. Sometimes their "yes" really is a "yes." If others have said no, how will you know that the impossible is possible? You'll have to ask a lot of questions, see proof of concept, and talk to other satisfied customers.)

Plus, think of it this way: If a contractor is willing to say "no" when appropriate, that means his or her "yes" is something you can usually count on.