Be prepared when you conduct an informational interview with questions to ask your interviewee. Below are 200 possible questions. Of course, you can't ask anywhere near this many in an interview of 20-30 minutes, but this plentiful list will ensure that you choose questions to which you really want the answers. 
General questions about your interviewee's career field: 

1.    What are the various jobs available in this field? 
2.    What types of training do companies offer those who enter this field? 
3.    In what ways is your occupation changing? 
4.    How is the economy affecting this industry? 
5.    What is the employment outlook like in your career field? How much demand is there for people in this career? 
6.    How quickly is the field growing? 
7.    What are the growth areas of this field? 
8.    Can you estimate future job openings? 
9.    What parts of the country offer the best opportunities in this field? 
10.    What are the opportunities in this career like in [geographical area you are most interested in]? 
11.    What is the typical entry-level salary in this field? 
12.    What is the salary ranges for higher levels in this occupation? 
13.    Is there a salary ceiling? 
14.    Aside from such visible compensation as money, fringe benefits, travel, etc., what kinds of mental dividends (such as job satisfaction) does this career yield? 
15.    Is this industry heavily regulated? 
16.    What do you find unique about your career field? 
17.    From everything you've observed, what problems can you cite regarding working in this career? 
18.    What skills or personal characteristics do you feel contribute most to success in this industry? 
19.    What sacrifices have you had to make to succeed in this field, and do you feel the sacrifices were worth it? 
20.    When people leave this career, what are the usual reasons? 
21.    What are the typical entry-level job titles and functions? 
22.    What entry-level jobs offer the best opportunities for the greatest amount of learning? 
23.    What are the most significant characteristics of this industry? 
24.    What trends in the field would be most likely to affect someone just entering this career now? 
25.    What kinds of people experience the greatest success in this field? 
26.    What is the most important thing that someone planning to enter this career should know? 
All about your interviewee's job: 
27.    What is your exact title? 
28.    Do other people in your company with the same job title that you hold have the same responsibilities? 
29.    What was your title when you first started here? 
30.    What precisely do you do? What are the duties/functions/responsibilities of your job? 
31.    What is your job like? 
32.    To what extent is it you expected it would be? 
33.    How much job security do you have in this position? 
34.    What is a typical day like? 
35.    What kind of hours do you normally work? 
36.    Do you have to put in much overtime or work on weekends? 
37.    Are the time demands of your job specific to this company, or would anyone in this career be expected to put in the same hours? 
38.    Do you ever take work home with you? 
39.    What kinds of problems do you deal with? 
40.    What do you do if you can't solve a problem on your own? 
41.    Do you have to deal with a significant amount of conflict in his job? 
42.    What systems are in place for dealing with conflict? 
43.    What constraints, such as time and funding, make your job more difficult?
44.    What kinds of decisions do you make? 
45.    Describe some of the toughest situations you've faced in this job. 
46.    To what extent do you interact with customers/clients? 
47.    What percentage of your time is spent doing each function? 
48.    How does your time use vary? Are there busy and slow times or is the work activity fairly constant? 
49.    Which other departments, functional units, or levels of the hierarchy do you regularly interact with? 
50.    How much flexibility do you have in determining how you perform your job? 
51.    Is your work primarily individual or predominately in groups or teams? 
52.    How are work teams or groups organized? 
53.    What are the most important personal satisfactions and dissatisfactions connected with your job? What part of this job do you personally find most satisfying? Most challenging? 
54.    What are your interests and in what way does this job satisfy your interests? 
55.    What do you like and not like about working in this job? 
56.    Do you find your job exciting or boring? Why? 
57.    Are there aspects to your job that are repetitious? 
58.    Is multi-tasking a skill that is required for this job? 
59.    What projects have you worked on that have been particularly interesting?
60.    What particular skills or talents are most essential to be effective in your job? 
61.    How did you learn these skills? 
62.    What are the educational, requirements for this job? 
63.    What other types of credentials or licenses are required? 
64.    Is graduate school recommended? An MBA? Some other graduate degree or certifications? 
65.    What obligations does your employer place on you outside of the ordinary work week? 
66.    What social obligations go along with a job in your occupation? 
67.    Are there organizations you are expected to join? 
68.    Are there other things you are expected to do outside work hours? 
69.    How has your job affected your lifestyle? 
70.    To what extent does this job present a challenge in terms of juggling work and family life? 
71.    What are the major frustrations of this job? 
72.    If you could change anything about your job, what would it be? 
73.    Is there a great deal of turnover in this job? 
74.    What interests you least about the job or creates the most stress? 
75.    What is the job title of your department head or supervisor for this job? 
76.    Where do you and your supervisor fit into the organizational structure? 
77.    How many people do you supervise? 
78.    How would you assess your prestige or level of status in this job? In the company? 
79.    If you ever left your job, what would most likely drive you away? 
About preparing for this career: 
80.    Does your work relate to any experiences or studies you had in college? 
81.    How well did your college experience prepare you for this job? 
82.    What courses have proved to be the most valuable to you in your work? 
83.    What courses do you wish you had taken that would have prepared you? 
84.    If you were a college student again, what would you do differently to prepare you for this job? 
85.    How important are grades/GPA for obtaining a job in this field? 
86.    What do you feel is the best educational preparation for this career? 
87.    How do you think [name of your college]'s reputation is viewed when it comes to hiring? 
88.    How did you prepare for this work? 
89.    If you were entering this career today, would you change your preparation in any way to facilitate entry? 
About your interviewee's career path: 
90.    In what way did this type of work interest you and how did you get started?
91.    What was your major in college? 
92.    How did you get your job? 
93.    Did you enter this position through a formal training program? 
94.    What jobs and experiences have led you to your present position? 
95.    What kinds of things did you do before you entered this occupation? 
96.    Which aspects of your background have been most helpful? 
97.    What other jobs can you get with the same background? 
98.    What were the keys to your career advancement? 
99.    How did you get where you are and what are your long-range goals? 
100.    What is the job above your current job? 
101.    If your job progresses as you like, what would be the next step in your career? 
102.    Where do you see yourself in five years? 
103.    If your work were suddenly eliminated, what kinds of work do you feel prepared to do? 
104.    If you could do things all over again, would you choose the same path for yourself? Why? What would you change? 
About the culture of your interviewee's company or organization: 
105.    Why did you decide to work for this company? 
106.    What do you like most about this company? 
107.    How does your company differ from its competitors? 
108.    Why do customers choose this company? 
109.    What is the company's relationship with its customers? 
110.    How optimistic are you about the company's future and your future with the company? 
111.    Has the company made any recent changes to improve its business practices and profitability? 
112.    What does the company do to contribute to its employees' professional development? 
113.    What systems are in place to enable employees to give management feedback and suggestions? 
114.    How does the company make use of technology for internal communication and outside marketing? (Use of e-mail, Internet, intranets, World Wide Web, videoconferencing, etc.)? 
115.    What other technologies are integral to the company's operation? 
116.    How would you describe the atmosphere at the company? Is it fairly formal or more laid-back and informal? 
117.    Do people in your department function fairly autonomously, or do they require a lot of supervision and direction? 
118.    What are the people like with whom you work? 
119.    How would you describe the morale level of people who work here? 
120.    Do you participate in many social activities with your coworkers? 
121.    Is there a basic philosophy of the company or organization and, if so, what is it? (Is it a people-, service- or product-oriented business?) 
122.    What is the company's mission statement? 
123.    What can you tell me about the corporate culture? 
124.    Is the company's management style top-down, or do front-line employees share in decision-making? 
125.    Is there flexibility in work hours, vacation schedule, place of residence, etc.? 
126.    What's the dress code here? Is it conservative or casual? Does the company have dress-down of casual days? 
127.    Can men wear beards or long hair here? 
128.    What work-related values are most highly esteemed in this company (security, high income, variety, independence)? 
129.    What kind of training program does the company offer? Is it highly structured or more informal? 
130.    Does the company encourage and/or pay for employees to pursue graduate degrees? Is there a tuition reimbursement program? 
131.    Does the company offer an employee discount on the products it sells? 
132.    What's the best thing about the company? 
133.    How does the company evaluate your job performance? 
134.    How does the company recognize outstanding accomplishments of its employees? 
135.    What does the company reward? 
136.    Are there people within or outside the organization that the company holds up as heroes? 
137.    Does the company observe any rituals, traditions, or ceremonies? 
138.    What is the typical job-interview process at the company? How many interviews do candidates generally go through before being offered a position?
139.    What does the company do to foster innovation and creativity? 
About the company's needs: 
140.    In what areas do you perceive there to be gaps in personnel in this company? If the company had unlimited resources for creating new positions, in what areas should those positions be created? 
141.    In what areas do you see the company expanding? Do you foresee the opening of new markets or greater globalization? Do you predict development of new products and/or services? Building of new facilities? 
142.    How can employees prepare for any planned changes at the company? 
143.    What obstacles do you see getting in the way of the company's profitability or growth? 
144.    If you needed someone to assist you in your job, what tasks would you assign to your assistant? 
About opportunities for advancement within this company and/or field: 
145.    How does a person progress in your field? 
146.    What is the highest-level job one can hold in this career? 
147.    What is a typical career path in this field or organization? 
148.    What are the advancement opportunities? 
149.    What is the average length of time for an employee to stay in the job you hold? 
150.    How rapidly do people move to the next level in this career? 
151.    What incentives or disincentives are there for staying in the same job? 
152.    Would someone in this field need to relocate to advance in his/her career? 
153.    If I performed well at this company, where could I expect to be in five years? 
Seeking advice if you are a career changer: 
154.    My current career is ________________________. How easy or difficult do you think it might be to make a transition from that career to your career? 
155.    The skills I use the most in my current career are ________________. To what extent and in what ways do you think those skills are transferable to your career? 
156.    What aspects of my background do you feel would be the most helpful in making the transition to your career field? 
157.    What aspects of my background do you feel would be the biggest obstacles to someone making the transition to your career field? 
158.    What skills needed in your career field do you think someone in my current career might be lacking and might need to develop? 
159.    What would be the best kind of training to get to make the transition from my current career to your career? 
160.    What's the best way for me to get more experience in your field without taking major steps backward from the level to which I've progressed in my current career? 
161.    How do you think someone in my current career would be viewed by those with hiring power in your career? Would you personally hire someone coming from my current career field? 
162.    The things I like the best about my current career are: _____________________. Will I find some of those same things if I switch to your career? 
163.    The things I dislike the most about my current career are: _____________________. Will I encounter any of those same challenges in your career? 
164.    Do you know of any other people in your career that have made the transition to your field from my current career or a career similar to my current career? How did the transition work out? 
165.    I've heard that people in your field have characteristics such as _______________________, which I have not had the opportunity to develop in my current career. How important is/are that/those characteristic(s). 
166.    What sacrifices do you think I might have to make to make the switch into your career field? 
167.    Knowing what you know about your career field, and knowing what I would have to do to get into this field, do you think you would make the change if you were me? If not, can you suggest any other fields that might be more appropriate for me? 
168.    Could you take a brief look at my resume and suggest ways I could tailor it to make myself more marketable in changing from my current career field to your career field? 
Seeking general advice and referrals from your interviewee: 
169.    Can you suggest some ways a person could obtain the experience necessary to enter this field? 
170.    What is the best way to obtain a position that will get me started in this occupation? 
171.    What do you wish you'd known before you entered this field? 
172.    What are the major qualifications for success in this occupation? 
173.    What are the skills that are most important for a position in this field? 
174.    What courses should I be taking? 
175.    How can I assess whether or not I have the skills needed for a position such as yours? 
176.    With the information you have about my education, skills, and experience, what other fields or jobs would you suggest I research further before I make a final decision? 
177.    Do you know of other people whom I might talk to who have similar jobs? 
178.    Do you have any advice for someone interested in this field/job? 
179.    Which professional journals and publications should I be reading to learn about this career? 
180.    Are there any other written materials (such as company brochures) that you suggest I read? 
181.    Which professional organizations associated with this career should I join? 
182.    What kinds of experience, paid or unpaid, would you encourage for anybody pursuing a career in this field? 
183.    Who else do you know who is doing similar kinds of work or uses similar skills? 
184.    What other kinds of organizations hire people to perform the functions you do here? 
185.    If I am unable to obtain a position in this field, what other fields would you recommend I consider? 
186.    What special advice do you have for a student seeking to qualify for this position? 
187.    Do you have any special world of warning or encouragement as a result of your experience? 
188.    These are my strongest assets (skills, areas of knowledge, personality traits and values):___________________________________. Where would they fit in this field? Where would they be helpful in this organization? Where might they fit in other fields? Where might they be helpful in other organizations? 
189.    What should I do to prepare myself for emerging trends and changes in this field? 
190.    How would you assess the experience I've had so far in terms of entering this field? 
191.    What qualifications would you be looking for if you were hiring for a position such as yours? 
192.    What qualifications would you be looking for if you were hiring for a position subordinate to yours in the office? 
193.    Do you have any written job descriptions of positions in this field/company? 
194.    What areas of the company would be most interested in hiring people with my background? 
195.    If I wanted to obtain a job here, who would the best person to contact? 
196.    If I wanted to obtain a job here, what would be the best way to learn of job vacancies? 
197.    If you were conducting a job search today, how would you go about it? 
198.    Would you be willing to answer more questions, by phone or in person, if I need additional advice in the future? 
199.    [If you feel comfortable and it seems appropriate:] Would you mind taking a look at my resume to see if you have any suggestions? 
200.    How would you react if you received a resume like mine for a position with this company? 
To learn much more about informational interviewing, read our detailed guide, the Informational Interviewing Tutorial. 
Questions about some of the terminology used in this article? Get more information (definitions and links) on key college, career, and job-search terms by going to our Job-Seeker's Glossary of Job-Hunting Terms. 
Be sure to take advantage of all the career networking tools, articles, and resources found in our The Art of Career Networking section of Quintessential Careers.