Most Inc. 500 companies hire their first chief information officer late in the game -- after sales directors and chief financial officers. Recruiting and hiring a CIO is tough for many company owners. Placement experts, management information systems directors, and CEOs who have recently made such hires suggest asking candidates certain key questions and then asking yourself whether their responses work for you.

Ask the candidate: How does a modem work?

Then ask yourself: Is the candidate able to explain simple technical issues? Does he demonstrate basic understanding, and can he define terms without relying on a lot of jargon?

Ask the candidate: What is the most difficult technical problem you've solved?

Then ask yourself: What is her skill level -- was the problem truly difficult? Did she correctly identify the key technical issues of the project? Did she also consider the business issues involved?

Ask the candidate: Have you been authorized to make technical purchases? Describe the purchases and how you proceeded.

Then ask yourself: Can he think through purchasing decisions for companies investing heavily in technology? Did he correctly identify the business needs of the company making the purchase?

Ask the candidate: How would you connect our six desktop computers in a local-area network?

Then ask yourself: Does she ask insightful questions about our needs and resources? Does she try to identify how employees use the technology?

Ask the candidate: What do you like and dislike most about your current job?

Then ask yourself: Does he like having hands-on responsibility for keeping everything in good order? Is his experience varied enough? Is he flex-ible? Will he take on a broad range of responsibilities while our company is growing?