I talk to a lot of people online, some of them want to help me or work with me as a contractor. Over the past year, I’ve assembled a set of questions I ask them in order to get a better idea of them and the kind of work they do. I’ve found their answers are more valuable than any portfolio or resume. It lets me see how they are and how it would be like to communicate with them. I’m sharing these questions here in order to help others and maybe get some new questions.

1. What’s your experience with X?

I use this question to have them talk about their expertise with a specific subject. It’s not terribly informing but sometime they’ll talk about the niche they work in or describe their ideal project.

2. What kind of projects do you enjoy?

People work better when they work on things they enjoy. Sure, we are all capable of working on things we don’t enjoy but isn’t it better to have everyone work on what will make them happy?

3. Thinking about all the projects you’ve worked on, which did you have the most fun writing/producing/doing?

What I’m looking for here is the ability for someone to turn a boring project into something fun. Sure building yet another backend office system might be dull; but if this one included a help system with a paperclip mascot that might liven things up a bit…

4. What are your strengths?

Some people have their niche, others are very broad and can do anything under the sun. But usually everyone is really good at something and the sooner you can find out about this, the better off you can be.

5. What are your weaknesses?

I use this question for two cases:

1. What are they genuinely not good at?
2. Can they be honest about themselves?

No one can be strong in everything they do. There is never enough time in the world to become great at everything. By knowing that someone sucks at picking colors, I can make sure to back them up with someone who dreams about color swatches.

My more important goal here is to find out how honest they are. If I get a answer like “I work too hard” or “I put the team ahead of myself too often”, I call foul. These are coached responses from trying to spin a negative into a positive. If you work too hard, that’s a positive. Now give me a negative.

6. Where do you want to grow?

If you’re not growing your skill set, it’s shrinking and shrinking fast. I’m not looking for specifics here usually, just seeing if the person has a growth plan for themselves or their business. If you’re going to take the time and risk working with someone, you want to make sure that you both are heading in similar directions.

7. How much lead time would I need to subcontract you? A week in advance, a month, etc.

Scheduling is funny in that you might have an entire month open one day and then get it reserved the very next day. Knowing how fast someone can be brought into a project is valuable if you need specialized talent. I’ve found that larger organizations count this in terms of months, while solo freelancers count this in terms of days or hours. Both are fine, as long as the time frame works with the project.

Tip: My response to this is “As soon as you sign the contract and I have the deposit, subject to my availability”.

8. Do you bill by the hour or project?

This is good information to get upfront, since pricing is all over the map. I just look to see if they fall within the project’s budget range.

9. What are your rates?

Same as above.

10. What’s one question I didn’t ask but I should have?

I’ve only recently started to ask this, and it’s turned out some wonderful results. Some people use this opportunity to pitch their services again, others use it to talk about their long term goals, and a few have used it to interject humor into the discussion. Humor is good, especially when working with me.

Response time

Another thing I look for is how quickly they respond. In general, I look for a 1-2 business day turnaround. Sometimes I get a response right away saying they need to think about it a bit. That’s a good sign, since it means that I’m not going to get a canned response and also that they were able to communicate to me quickly and set expectations.

Those are the questions I use when I’m approached by a new contractor or service provider. What questions do you think work good? Is there anything you would add?