3 Critical Questions To Ask When Hiring a Branding Photographer

Is 2022 the year you finally make the move towards hiring a personal branding photographer to take your content to the next level?

Melissa Hollingsworth Creative Director Worthwhile Media

Maybe you’re tired of DIYing your content or you’ve been using the same photos since—well, way past their expiration date (yep, we’re in the ’20s now so those pictures from 2018 are from the last decade). 

Earlier this year we did a blog post called When to Hire a Full-Time Photographer. In that post, we walked you through seven questions to ask yourself to help determine if you are ready to hire a personal branding photographer. If you missed that post, or just need a refresher, you can find it right here 

After that post, we had a lot of questions from people outside our local market area seeking help on what to look for and ask about when choosing a branding photographer. 

We know we can’t serve everyone with personal photography services, so we thought it would be a good idea to walk you through what you should ask a photographer you’re considering hiring during your discovery consultation. (And if they don’t offer a complimentary consultation, consider that your first red flag!) 

In today’s blog, we’ll walk you through the three most critical questions to ask (and provide the answers we think you should receive) when hiring a personal brand photographer. 

First things first, after you’ve checked out the photographer’s online presence (website, social feed, reviews) there’s one more thing I would do. It’s time to contact one of their clients—I call it a direct message case study that helps you determine if the way things are portrayed online is how things play out in the real world. Just be sure to make it easy for them to answer by keeping your questions short and simple. A quick, “would you hire branding photographer again?”  leaves them room to expound as much (or as little) as they want without feeling pressured.  

If, after checking this off your list, you still think they might be a good fit for you and your branding photography, set up a discovery call. 

During your conversation, you want to determine both if this is someone you could see yourself working with—being comfortable and confident in the lens of their camera—and their level of professionalism and experience.  

It’s a lot to think about, but don’t worry, we’ve got you covered—keep reading for the three critical questions to ask.

Let’s Talk Licensing

Question 1: Is commercial license included in all the images? 

If the photographer doesn’t have an answer for that question, run, and if they don’t know what that is, run faster! 

A commercial license should be included for all the photos so that you can use them how you like, including for commercial purposes. Of course, you’ll want to use them in your social feed, but also for any PR outreach, advertising, marketing, printed materials, etc. A traditional portrait photographer often only includes a license for personal use or may allow you to post the images on social media, but not create marketing materials with them. You need to make sure the photos you receive are licensed to be used in the way you want to use them. A “full commercial license” should do the trick. 

Tip: Be careful not to confuse commercial license with copyright—the photographer will always maintain the copyright on the image but will offer you the license. If you ask for the copyright, most photographers will say no because if they give you the copyright it means they can’t use the images for their own marketing purposes. If you are concerned about how your images will be used, just have a conversation with your photographer. Most are happy to comply with your wishes without the need to transfer copyright. 

So, be sure to ask, are the images licensed for commercial use? The details of your license should be included in your contract. 

Additional Asks and Advice

  1. Can you provide the photographs in multiple file sizes? Or what file sizes am I going to receive? (You’ll want hi-res images, but if the photographer can provide additional web-sized images that can be very helpful.)
  2. Do you provide digital images?  (This answer needs to be yes.) 
  3. Is any retouching included? (Sometimes this is included with the original price and sometimes there is an additional fee – either option works.)


Photography, like any craft, has many areas of specialization. Portrait photographers often don’t provide digital images. Event photographers often don’t provide retouching. Many amateur photographers don’t understand commercial licensing. Make sure you connect with the right photographer for the job!


Will I Look Good?

Question 2: Can you make my nose look smaller? Hide my double chin? Help me look like I’ve got smaller hips? 

We all have that one thing that stands out to us in photos of ourselves—and not in a good way. It’s different for everybody, and it blows my mind how many times I have absolutely beautiful, gorgeous people standing in front of me, and they get tripped up about that one thing that will bother them in every single photograph if it isn’t addressed. 

Sometimes it’s a lazy eye, sometimes it’s puffy cheeks or a big nose, whatever it is, we all have something. We look at the photo and that’s all we see and really, it’s ok. This isn’t a call to get over our insecurities, though, wouldn’t it be great if we could. This is a reminder that sometimes what you see is just bad photography- and there is an easy fix for that 

Let me start with a story. Recently, I have put on more weight, and I don’t love that I have, but we all go through this. The thing is, I can look at myself in the mirror, and I feel confident in my body, so I’m very thankful for that. 

I don’t dislike the way my body looks. I’m a little fluffier, but I’m OK. I even think I look good on video conference calls because I know how to work my angles and hit the light. Because I’m a photographer, I can move my body and put it in a position where I go, yeah, that looks good. 

However, right now when I look at photos that other people have taken of me, I’m so sad. Recently we were hiking and I wanted my picture taken by a waterfall. So, I handed the camera to my husband. Now, I love him, and he loves me, but those pictures—they’re not flattering at all. 

Had the camera been in my hands, I would have loved them because I know how to use lighting and angles. It’s not your job to know how to do that in the same way that it’s not my husband’s job to know how to do that- he has skills in other areas. As for me, however, my skills fall heavily in making people look good. 

So, I understand. I even battle some of those thoughts when I look at these photos of myself that other people have taken. I know that’s not what I look like, it’s just the one representation captured in time that was not the right capture. 

This is where trust with your professional photographer comes in, yes, but photographer experience plays an even bigger role. It’s the camera angle and it’s your body angle—both are important. Bottom line: your photographer should know how to work the camera angles, your angles, and the lighting to make you look and feel gorgeous in every photograph. And they should care enough to listen to your concerns and act accordingly—even if they only see a beautiful person in front of them.  

Additional Asks and Advice

  1. Can you help me hide my big chin? Or I don’t love my left side, can you be sure to get me mostly from the right? Whatever your one thing is, now is a great time to discuss it with your photographer. Talk about past photo shoot experiences if that helps you express your uncertainty. Then listen carefully to the photographer’s response. Are they listening and offering solutions, making notes? If they say they can take care of it ask them how. They probably won’t give away all their trade secrets, but hopefully, they will offer you a few hints at their tips and tricks for making you look good.


Here at Worthwhile Media, we use lighting, makeup, and angles to make sure we capture you just the way you see yourself (or better if that self-esteem needs a little boost). It’s not about changing your appearance; it’s about capturing the best representation of your true self. 

Who is in Charge?

Question 3: Will you provide the direction for our shoot?

Hopefully, you’re still here because I saved the most important question for last. This separates truly professional branding photographers from the rest. The right answer to this question will have you enjoying your time during the shoot and walking away with images that you are proud of. 


When Lauren Gall and Melanie Ammerman, owners of  VaVa Virtual Assistants, came to Worthwhile Media they needed fantastic headshots, environmental portraits, and storytelling-based photography to represent both themselves and their company in their marketing materials. They had worked with other photographers in the past and while the photographs were useful; the experience was stressful, unorganized, and lacked the direction they were looking for from a photographer. You can read their case study about working with Worthwhile Media on our website here 

We want to help you avoid this experience, so you should ask a few questions to determine the level of involvement the photographer will have beyond showing up on the day of the shoot and creating the images. 

At Worthwhile Media, we believe the work that takes place during Pre-Production is just as important as the work that takes place during Production (the day of your session). There is a lot your photographer can do to help you prepare for your photography session, but not every photographer does these things. Here are a few questions to ask to learn how involved your photographer will be in the planning process: 

  • Do you have any ideas for what I should do in my photos? 
  • Do you help with wardrobe selection?  
  • Do you plan out the shots for me or do I have to do that myself? 
  • Do you have any creative ideas for my photos based on what I’ve told you?  
  • If we are shooting outside, do you have a plan for if the weather goes bad?  
  • What about where we will shoot, do you come up with that or do I?


All these questions are really asking one, bigger question: are you just a photographer or are you a Creative Director? 

Often a client finds a photographer that can take excellent photos, but everything else is put on them. You don’t want a photographer that will stand there on the day of the session and say, “So, what do you want to shoot?” The customary response from the client in that situation is usually something like, “I thought it was your job to tell me what to do.” And really, it is.

You want a photographer that will help you plan out all of the shots in advance so that the day of the session runs smoothly and professionally.
They should be an expert storyteller in addition to being an expert photographer. The success of your brand depends on it.

You have enough things to worry about in running your own business – the fine details of your photography session shouldn’t be one of them. Find a photographer that will help you work out the details of your wardrobe, hair and makeup, locations, props, and most importantly, the stories you’ll capture in your images. If you were a branding expert, you’d probably have a branding company. Since
you don’t have a branding company, find a photographer that understands how to capture images that will bring in clients and customers and highlight your brand in the best way possible.

Additional Asks and Advice 

I want to encourage you to look for a photographer that is going to be a creative director and not just a photographer because that is the biggest headache I hear from clients who find me after one or two photoshoots with a different photographer. If all you need is a portrait, any of the amazing portrait photographers out there will do, but if you need images for your brand, you need a photographer that is also a storyteller. So, the biggest question to ask is: 

Can you take my brand and help me plan a photoshoot that will speak directly to my audience and drive conversion?

(And if you aren’t sure how to effectively communicate your brand to your photographer, be sure to subscribe to our email list! We’ve got a post coming up where we will walk you through how to do just that and will let you know when it goes live!)

Don’t Be Afraid to Ask the Questions

If I was seeking to hire a personal branding photographer, these are the big questions I would ask. You want to work with someone who makes you feel at ease in front of the camera. Ideally, this is someone who can become a member of your team long-term because the more you work together the more comfortable you will become in front of the camera and that will show in your images. Remember, you are the one paying for this session, it’s you and your brand reflected in these pictures. You want and deserve results you will love and be thrilled to share.  

If you are ready to hire a full-time photographer or just want to taste what it might be like to work with a pro in a single session, reach out to Worthwhile Media. We’d love to tell you more about how subscription-based photography can help you reach your audience, boost your brand, and bring customers and clients to your doorstep. 


Worthwhile Media is a full-service branding agency focused on custom content creation through effective storytelling in the mediums of photography, video, and the written word. Offering subscription-based services and single photography and video sessions, they provide images and content for web, print, social media, and public relations. From headshots and banner reels to seasonal marketing campaigns, Worthwhile Media is available to meet all your content creation needs. Reach out today to schedule your free discovery consultation. 





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3 Critical Questions To Ask When Hiring a Branding Photographer

  1. […] our blog post on the 3 Critical Questions To Ask When Hiring a Branding Photographer, we included several of the questions you should ask a photographer before you hire […]

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