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The Aspirational Interview Guide

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Informational Interview Guidelines

One of the most valuable tools available to anyone is the informational interview.  Use this tool any time you’re thinking about changing your business, diversifying into a new area or just need some information you couldn’t get any other way.  

The following tips are intended to help you conduct an aspirational informational interview.  An aspirational interview is when you’re talking with someone whose career path is one that you aspire to match; there’s something about their work, their client base, their reputation and/or their public image that is close to something that you want in your career.  I’ve also included suggestions for interviewing people on the client side to gain insights into what they really care about.

Keep in mind that the best interviews flow like a conversation - use your questions as a road map, not as a script.  Steer gently towards the areas that you're most interested in learning more about.  Ask open-ended questions, encourage the person to talk, listen actively.  

Don’t disagree or argue with them and don't use their time to talk about yourself or ask them to solve your problems.  Focus on learning as much as you can about them – you can evaluate what you learn and decide what you want to take from the conversation after it’s over.

Identifying Potential Aspirational Interview Candidates

The ideal aspirational informational interview candidate is someone whose creative work blows you away and whose career path is one that you aspire to follow.  People who fall into just one of those 2 categories can also offer valuable insights but be sure to focus the interview on what you most want to learn from them. 

The following sites aggregate photographers portfolios and can be a useful tool for identifying potential informational interview candidates:

WorkBook • www.workbook.com

WorkBook hosts a searchable database of professional photographers, CGI artists and retouchers with sample images and links to their websites as well as a directory listing ad agencies & design firms, stylists, reps and other resources for photographers.

Alternative Pick • www.AltPick.com

Alternative Pick generally features imagery that’s a bit more conceptual.  Again, their directory features a wide range of talent including photographers, CGI artists and retouchers.

Communication Arts • www.commarts.com

CA publishes some of the most prestigious awards annuals in the United States.  Their Creative Hotlist  functions as a searchable directory of photographers. Their Gallery section can be sorted to show award winners in photography, advertising, design, etc.

Wonderful Machine • www.wonderfulmachine.com

Wonderful Machine offers a la carte marketing and production services to a select group of photographers.  As part of their marketing services, they host searchable portfolios of their members’ work. 

At Edge • www.at-edge.com

Limited to 155 hand-picked photographers and post-production artists per year, At Edge features some of the most innovative and high-end photographers doing advertising and editorial still and motion photography today. 

Industry publications and blogs such as Photo District News, fstoppers, Petapixel, aphotoeditor.com, and Resource Magazine can also be good resources as can visually based social media platforms like Instagram or motion platforms like YouTube and Vimeo.   

Asking for an Interview

Before reaching out for an informational interview, be sure to review the candidate’s website and social media presence. Google them and read any articles or interviews that show up.  Stop well short of stalking them but review any information that’s public so you can reference your familiarity with their work and avoid wasting time asking questions they’ve answered elsewhere.

The more successful the candidate is, the harder it may be to reach them - sometimes, establishing a relationship by commenting on their blog or engaging through social media before reaching out for an informational interview can help. Obviously, if you know anyone who knows your subject, don’t hesitate to ask for an introduction or to include your mutual friend’s name in the subject line of your initial message (e.g. Referral by Joe Smith).

Even if you don’t know anyone in common, you’ll be amazed by how many people will respond to a sincere request for help from a stranger.  There’s no need to write a novel, but including an explanation of how you found them, what you love about their work, and what you’d like to interview them about will increase the likelihood they’ll say yes.  

Here’s a sample email my partner has used successfully to solicit informational interviews from some of the top CGI artists in the world:

Hi  [Name],

I’m reaching out to you today in the hopes that you might be willing to share some of your knowledge about working in the CGI industry.  

I first came across your work in [XXX] and was blown away.  I particularly love the campaign you did for [YYY].  After reading your interview in [ZZZ], I’m even more impressed.  Your observations about [this] and [that] were particularly invaluable.

My partner and I have been working as advertising photographers for the past 26 years.  We were early adopters of digital photography and have always strived to create images that make the ordinary extraordinary.  We are looking to make a career change into doing CGI and would find it enormously helpful to get your insights into how the industry works and the state it’s currently in.

Is there any chance you might be willing to hop on the phone and answer a few questions for us in the next few weeks?  We understand that you’re busy but it would mean the world to us and we’ll do our best to work around your schedule and keep the call short. 

Thanks so much and we’ll be looking forward to hearing your thoughts!


This example illustrates just one approach.  The message you send should be in your voice and should express how you sincerely feel about the person’s work and contributions. 

Drafting Your Questions

Here are some areas that you might want to cover in the conversation - remove, add or customize questions as needed based on your goals for the interview: 

On getting started

  • How did you get started?

  • If you were starting now, what would you do differently?

  • What's the biggest mistake you made when you were first starting out?

Obviously, the last two are variations on the same theme.  Depending on the response to your first question, you might ask either or both of the other two questions.  If you ask both, you'd adjust the order based on how the person responded to the first question.

On lifestyle

  • How many hours/week do you typically work?

  • How do you spend most of your time?

  • How much of your time is spent shooting (or doing retouching/photo-illustration)?

  • What's your favorite part of your job?

  • What do you like the least?

  • How do you balance work and family life?

Again, adjust the order based on how the person responds.  Only ask the last question if you feel you've established enough rapport to get away with it.  The answer to the second question might render the third one obsolete but if they don't actually tell you how much time they spend doing creative work, it's a very good question to ask.

On business development

  • How much of your business comes from repeat clients?

  • How much energy do you put into keeping clients vs attracting new ones?

  • How long does it usually take to build a stable client base?

  • What marketing approaches do you use for your company?

  • What's the most effective marketing approach you've taken?

  • Do your new clients come mostly from promotional efforts or word of mouth?

  • What role does social media play in your marketing efforts?

On pricing

  • How do you figure out what to charge?

  • How did you learn how to figure out what to charge?

  • Do you offer any promotions or incentives?

The following questions may be more appropriate for the retail market since the projects are more consistent than the commercial side but even commercial photographers should be able to discuss how much time and money various scenarios might involve.

  • How much money, on average, does each client spend with you?

  • What's the minimum a client has to spend for you to be willing to take a job?

  • From start to finish, how much time do you typically spend per client?

  • How is that time divided between activities like shooting, post-production and client communications?

On the team

  • Do you have a partner or any full- or part-time employees?

  • Do you work with free-lancers?

  • Do you have a rep?

  • Are there any other businesses (besides clients) you work closely with?

If yes,

  • What are you able to delegate?

  • What do you have to do yourself?

  • What should I think about before adding an employee, entering into a collaborative relationship, hiring free-lancers, etc.?

If No,

  • How do you manage to do everything yourself?

  • Have you ever had employees (reps, partners, etc.)?

  • Do you want employees (a rep, partner, etc.)?

On the future

  • Where do you see yourself in 5 years, what's next for you?

  • Where do you see your industry going?

  • What skills do you think someone in your industry will need in 3-5 years?

  • What resources do you use to stay on top of new skills and information?

Remember, ask only those questions that will get you the information you most need to move your career forward and adapt this list as needed to serve your goals.

Identifying Potential Client Side Aspirational Interview Candidates

Your ideal target is someone who hires people to do the kind of work you wish to do.  They might work for a newspaper, magazine, ad agency, design firm, brand or corporation, non-profit organization, or a non-governmental organization.  They could be a gallerist, museum curator, collector or even a bride or family looking for portraits.  They might have job titles like photo editor, art director, art buyer, creative director, communications manager (or V.P.), social media manager (or V.P.), brand development manager (or V.P.), Director (or V.P.) of Content or Content Strategy, etc. They may be someone that you have worked with in the past or someone you aspire to work with in the future. 

The most important criteria is that the person you interview legitimately qualifies as someone who hires people to perform the kind of creative work you really want to do for a living.  

The following sites can be a useful tool for identifying potential informational interview candidates:


Trade publications like Ad Age, Adweek, Communication Arts, etc. frequently feature specific individuals at agencies or brands that could be viable prospects for you.  Industry specific publications often run feature stories on the movers and shakers of their industry along with ads from leading companies.  For example, if you specialize in the Aviation industry, Avionics Magazine might be a good resource.


Industry awards can be a great way to identify people doing more innovative or interesting creative work.  Look for awards annuals published by trade magazines like Photo District News, Communication Arts, Graphis, How, etc.  as well as industry awards like Addy’s and Clio’s.  There are also several websites that curate successful creative campaigns like Ads of the World, We Love Ad, and AdWeek’s Ad Freak section.  All of these resources publish visuals of the winning piece along with the names of everyone involved so they’re a great source for identifying creatives you’d like to interview and/or work with.


Searchable databases like Agency Compile and Redbooks, let you look up the agency of record for specific brands or search by agency to see their client roster.  Look, too, for databases that list creatives looking for clients like Communications Arts Hot List and FreelanceArtProducer.com.

Image/Video Searches

If you see an image or ad that makes you think the creatives behind it might be a good fit, you can try to track them down through a reverse image search or searching YouTube and/or Vimeo if it’s a motion project.

Drafting Your Questions

The goal of interviewing clients is to gain as much insight as possible into the client’s perspective when they are looking for and hiring still and motion photographers.  Look at the Client Avatar Worksheet below and think about the best way to get the answers to those questions from your subjects.  To be clear - the questions on the worksheet are not intended as a script for your interview.  Instead, you should craft questions that will elicit the information you need to complete the worksheet.  

Client Avatar Worksheet

Answer the following questions as thoroughly and with as much detail as possible:

  • Describe your ideal target customer - who needs/wants your product or service the most?  

  • What problems are they really trying to solve?

  • Why does solving those problems matter to them?  How does it benefit them personally? How does it benefit their company or client?

  • How do they feel about having to purchase your product or service?

  • What do they look for when purchasing the kind of product or service you sell besides the imagery itself?

  • What concerns do they have when looking for a solution to the problems you solve for them?

  • How can you make your offerings exceed their expectations?

General Interview Guidelines:

Don't feel like you have to ask everyone you talk to everything you want to know.  Pick the questions you want to ask based on what it is about that person's business that inspired you to call them.  Aim for a maximum of 20-30 minutes - if the person's willing to talk longer, that's fine but after 15-20 minutes say something like "This has been wonderful.  Am I taking up too much of your time or could I ask another question or two?"  Let them say "No, I've got a few more minutes" or get off the phone if they want to.

With that in mind, pick the 4 or 5 areas that are most important to you.  Ask your questions in order of importance so you can be sure that you cover the stuff you really want to know before you run out of time.

Remember, if you don't complete an informational interview feeling like you just learned something you couldn't have gotten any other way, you're asking the wrong questions.

Try to interview by phone whenever possible.  If your subject insists on e-mail, limit the number of questions you ask so the person isn't spending more than 15-20 minutes answering them. 

If you get a gatekeeper who won't let you talk to your interview subject, don't hesitate to ask them if they'll talk to you about their job.  You can learn an awful lot from studio managers and assistants, too.

Let Their Network Work for You

A great way to expand your pool of potential informational interview subjects is through the people you’ve already interviewed.  

The one question you should ask everyone you talk to is: “Who else do you know that might be willing talk to me?”.

If your interview subject gives you a name, be sure to follow up promptly as there’s a good chance that they will shoot that person an email saying that you’ll be in touch for an interview.

When you reach out to their friend, reference your interview subject in the subject line of your email (e.g. “referral from XXX”) as that will increase the chances they’ll open your message.  The first line of your email can then be something like “I spoke with XXX who suggested that I talk to you,” which will dramatically increase the likelihood that the friend will say yes.