1. Do you have a “day job”? Are you moonlighting?
Depending on your needs, you’ll either be comfortable with someone who is only available part time, or you’ll need someone who is committed to providing tech service full time.

2. Are there any other people who work at your company?
Find out if the consultant is a solo practitioner or part of a larger firm. If you discover he’s part of a consulting firm, find out if others from the firm will be involved with your account, and what their backgrounds, specialties, and history with the company are.

3. What “size” is your typical client?
Determine what size business the consultant is most experienced in dealing with. Signing on with a consultant who works mostly with large companies might mean he has great experience working with many PCs and employees, but it also means he’s used to companies with bigger budgets than yours.

4. Does your company specialize in any particular products and services?
Find out what software and hardware the company specializes in fixing, installing, and maintaining as well as the service vendors it might work with. Also, discover what types of technology they shy away from.

5. Does your company resell products, such as hardware and software? Are there any other vendors, such as ISPs or telephone companies, that your firm acts as an agent for?
Signing up with a reseller could put you in a position of only using the products they’re selling. Working with a true consultant, however, you’ll be able to shop for your choice of products and services.

6. What are your payment terms, rates and minimums?
Discover what kind of work is billable vs. non-billable. Also, ask how much the firm charges for travel time, phone support, e-mail/online support, and remote support, and whether there’s an increased charge for after-hours emergencies.

7. Can you provide references?
Ask the consultant to discuss long-term and more recent accounts with you to help get a better sense of his experience and abilities. Also, ask about those clients who didn’t work out and why they didn’t work out. This could reveal any potential pitfalls of a relationship with the consultant before you sign on with him.

8. How do you keep up with new tech developments?
What is new today can be old tomorrow, so it’s important that the consultant you work with knows about the latest tools and trends. Find out how the consultant keeps up with technology. Does he attend regular programming classes or certification classes regularly?

9. What kind of user and technical training can you provide?
The more handholding a consultant the more money he makes. Ask the consultant whether or not he would be willing to train you or someone else internally to become more self-sufficient.

10. What am I paying for?
Besides understanding the exact services you’ll be paying for, you’ll also want to know what type of overhead is built into the consultant’s rate structure. This way you’ll get a good feel for whether you’re paying for fancy cars and posh office space or working with someone you feel you’re getting the most bang for your buck from.