So about those new headshots you’ve been putting off for….years. It’s finally to the point where you dread the request, “send us your photo” because the photos you have represent an old version of you. Having to confront exactly who the current you is, and how you want to communicate that to the world, can cause some anxiety. 

How do you go about choosing a photographer? Here are my Top 5 Tips:

1. Start at the end (Decide what result you want.)

Before you go ask everyone you know if they “know a photographer”, here are the basic questions you want to have answered, so that your search can be efficient and successful:

  • What’s the look and feel you’re going for? Every photographer has their own style and specialty.
  • For what purposes will you use the photos? In other words, who’s your audience and what will have the desired effect on them? 
  • Know what mediums will you use. Print? Digital? Website and social media? Advertising? The side of a bus? 😉 Your photographer should have experience in those mediums. Not every style of photo looks good everywhere.

2. Don’t base your decision primarily on price (a.k.a. don’t be cheap).

Being on a budget is normal. No one wants to spend a lot of money on photos. Yes there are student or starter photographers out there offering low prices, and they may be really talented. However raw talent is not all you need (see #4: what to ask). A photoshoot is something that most of us want to do as seldom as possible, so the result needs to be AMAZING. I’m a big believer in “you get what you pay for”. You pay a top-notch photographer a higher fee to compensate them for their years of experience and for their TALENT that’s actually priceless.

3. Know your numbers

How many ‘looks’, headshots vs. action shots, vertical vs. horizontal, etc. do you need? I suggest you make a list to make sure you don’t forget anything. Here’s an example:


Vertical or horizontal





Typing on my computer


LinkedIn posts


Writing in my journal


Insta posts

Vertical, crop to square

Holding a capuccino 


**These are all jokes. Please don’t have shots like this taken. Even if your work mostly consists of you typing on a computer, we don’t need to see that! But I digress. That’s a whole other subject I address in a separate blog.

4. Request a video call.

You need to have a click with your photographer — to feel completely at ease with this person so that you don’t flash your ‘deer caught in headlights’ smile. The best way to find out in advance if your personalities are a fit is to schedule a video call to discuss the details of the shoot. Here’s what to ask:

  • What is your vision? Why are you doing this work? Tell me about a favorite shoot. What did you like about it?
  • Tell me about the preparation process. (Red flag: if they don’t have one, or don’t offer much detail. At a minimum they need to discuss the list of shots you need: the mood, the setting, the lighting, hair, makeup & clothing. If they’re really good, they’ll walk you through the process of how you need to prep for the shoot.)
  • My biggest fear is________/I really dislike_________/any other objections; what’s your advice on that? (You’re testing their experience and their emotional & social intelligence. You want to get a sense of whether they’re open to your input, or do they say, “Just trust me.”?
  • Tell me about the package — what’s included? A hair & makeup artist? A wardrobe stylist? How many shots and outfit changes? Confirm you’ll be able to use the images wherever you like, for as long as you like.
  • A good photographer should start by asking YOU lots of questions. If they don’t, that’s a red flag. It’s your shoot and you have to get the result you want, which becomes really difficult if you don’t give lots of input early on in the process.

Did the photographer put you at ease during the call? Were they able to make you laugh? Did the call end with you feeling reassured and excited, or doubtful and anxious? Trust your gut.

5. Don’t overthink it.

After steps 1-4, you should have a good feel for a photographer and whether they can do the job in a way that makes you feel fabulous. When you approach a photoshoot like a project and lose the feeling aspect, the photos will most likely show that. You will plan the creative process right out of the experience and wind up with images that are businesslike, but soulless.

Of course you knew that I wasn’t going to end without offering a solution to your photo dilemma. Incredibly talented photographer Cristina Stoian and I have put together The Brand You Experience — a  completely personalized photoshoot including wardrobe styling (2 outfits, 3 prints). Update your image and have fun doing it! Click here for full details, or click one of these links to book a chat with Cristina or me.