• Dean Birinyi

The Executive Headshot Success Guide: Part 3 -Selecting Your Photographer

Since opening my headshot studio in 2019, I've come to realize that most people don't know which questions to ask a photographer. In response, I've written the Executive Headshot Success Guide, which you can view online or download.


Below is the complete article on selecting your photographer. Following these guidelines will help you make good decisions about which headshot photographer in San Jose you choose to help you project your executive presence in your headshots. (Of course, I hope that would be me.)


Selecting your photographer:

The wrong photographer will not give you the right headshots

Unless you're an experienced marketing professional, you probably don't know how to evaluate creative service providers. Here's a step-by-step guide to help you make a good decision.

  • Define your needs, and then set your expectations.

  1. To prevent mission creep, write out why you need new headshots: Job search, company website, promoting a book or speaking tour, press release, etc.

  2. Decide how you want to be perceived by the decision-makers who see your headshots: relationship builder, innovative creator, decisive leader, etc.

  • Explore your options.

A confident man's headshot, by Dean Birinyi, a professional headshot photographer in Palo Alto

  1. Ask a friend who raved about their recent headshots for a referral to their photographer. Past success is a good indicator of future performance.

  2. Search on Google. Limit your search to photographers who specialize in headshots by specifying "headshot photographer" (include the quotation marks), ensuring you'll get immediate, relevant results.

  • Review photographers' websites and shortlist the ones whose work you like the most.

  1. Who you choose to shortlist depends on how you've determined you want to be perceived. One photographer's work may be polished and have a solid commercial feel; another will be casual and down to earth.

  2. Headshots are all about first impressions, and the first impression you get from a photographer's website should influence your decision to shortlist them or not.

  3. Select three or four photographers who feature headshots of people looking like how you want to look.

Photographers show the work they are most proud of on their websites. The style and type of photograph they want you to associate with them.
  • Now is the time to look at the price.

  1. Never spend more on your headshots than you can easily afford.

  2. If you're looking for a $150K+ position, $2000+/- is appropriate. You'll spend that much on a suit and get less traction.

  3. If you're in management looking for a promotion to a director, $800 - $1200 might be just right for you.

  4. If you're looking for an entry-level position, $100+/- is about all you should spend.

Photographers put photos on their website to be judged by you. The goal is to help you decide if they deserve your trust.
  • Interview the photographers on your shortlist over the phone or Zoom to learn if they're the right kind of person for you.

  1. We all have our personalities, and that influences our approach. As an example, my mentor, Peter Hurley, has a larger-than-life personality. He might be the perfect photographer for you, or you may prefer to work with someone with a nurturing, thoughtful approach.

  2. Ask about the photographer's process. Put them on the spot and see how they respond. Do they know what they’re doing or making it up as they go along?

  3. Ask about their studio. Choosing a photographer who works on location requires you to be comfortable performing for an audience.

After you hang up the phone or end the Zoom meeting, answer these three questions. Of the photographers you interviewed:

  1. Who do you like the most?

  2. Who respects the value of your professional image the most?

  3. Who do you trust to lead you through your headshot session the most?

All of this requires a good investment of your precious time. The return is headshots that make you look good and work to help you advance your career.