10 Questions to Ask Before Booking Your Headshot Photographer
Whether you’re updating your LinkedIn profile pic, finally replacing that cropped car selfie, or doing a fully rebranded website, professional headshots can be a game changer in how you present yourself to the world.
But not all headshot experiences – or photographers – are the same.
The right photographer for you won’t just take a technically good image. They will understand who your target audience is, how you want to present yourself, and how to help YOU relax to take a great picture that’s approachable, confident and polished. Like yourself on your best day.
Here are are 10 questions to ask before you book your headshot session…
1. What style of headshots do you specialize in?
There are lots of different headshot styles. Dramatic editorial images, bright, approachable corporate images, creative concept headshots to name a few.
There’s no “right” style, just the style that fits you and your goals.
Before booking, make sure your photographer’s portfolio reflects the looks you want for your business, industry, and personality. An attorney’s needs might be very different from a realtor, a therapist, or a creative professional.
If the look you want is unique and not found in exisiting portfolios, then just look for consistency. Watch for whether every image in the portfolio feels polished and natural. That’s a good sign you will receive the same results.
2. Will you help me feel comfortable in front of the camera (and how?)
This may be the most important question of all. A techinically beautiful portrait of you is essentially worthless if you don’t like how you look.
Most people don’t love having their picture taken. In fact, most of my clients tell me they don’t take a good picture. That’s simply not true for most people, but it does take preparation to create an environment where someone can relax enough to take a great picture. A good headshot photographer will guide you through expression, posture, how to position your feet, hands, head… everything.
And more importantly they will take the time beforehand to know enough about you that you will feel relaxed, confident, and genuinely comfortable in front of their camera.
3. What should I wear?
A professional headshot photographer should provide guidance before your session, not leave you to figure it out.
Ask whether they help with:
- Wardrobe selection
- Color recommendations
- Accessories & jewelry
- Necklines
- Glasses considerations
- Industry-specific styling
The goal is to choose clothing that photographs beautifully, flatters you, and supports your personal brand. Your photographer should be able to guide you in selecting exactly that.
For every custom session, we work with each client to select their wardrobe for their session together beforehand. We consider who the intended audience is, how the images will be used, and what will photograph well and be flattering on camera. Because that’s not always the same thing as what is flattering in real life!
4. How can I use my images?
A headshot photographer should also ask you how you want to use your images. In order to know what you need, it’s helpful to know how you plan to use them. The intended use helps determine wardrobe, lighting, background choice, expression, and overall creative feel.
Some of the more typical uses inlcude:
- LinkedIn Headshot
- Profile Portraits
- Corporate Bio
- Speaking engagement
- Personal brand launch
- Website launch or rebrand
- Medical or legal profile
- Social media content
- Press features
A great headshot session is strategic – not generic.
5. Do you offer traditional headshots, branding portraits, or both?
I frequently have clients that start by saying they need a headshot, but when we start talking through how they want to use their images they realize what they really want is branding portraits. Traditional headshots are typically tighter, cleaner, with fewer background elements or distractions, and more straightforward. Branding sessions tell a full branding story, and typically include
- Environment portraits
- Documentary imagery
- Greater variety of wide and tight compositions
- Lifestyle imagery
- Workspace details
- Multi-person interactions
- Brand-aligned content for website backgrounds and social media content
If you want content to support your marketing efforts across multiple platforms like social media, website, print marketing, etc., branding portraits might be what you need.
6. What is your retouching style?
Professional retouching should look natural and polished, not flat or plastic. But retouching style is a personal preference, so this is another place where it’s helpful to look at the portfolio and see if their style is in line with your preferences.
You should look like yourself. Just rested, polished and camera ready. If you prefer a little more or less than what you see in the portfolio, then just ask how much flexibility there is to meet your specific needs.
While we prefer a very natural look that retains all texture but softens color variations for a polished but not overly-processed look, we occasionally have clients that ask for more or less retouching based on personal preferance.
7. How long does the session take?
Some photographers offer quick 10-15 minute in-and-out sessions, while others build time for wardrobe changes, caoching, and expression variety.
Things to know about timing are:
- How long the session lasts
- How many looks are included
- If outfit changes are accomodated
- How much image variety you can expect
- Is there a max session time (lets you know if more wardrobe changes will reduce total shooting time)
For people looking for a quick 15-minute session, I can already tell you what we do is not for them. But I know some great headshot photographers that would be happy to work with them. We work hard to create a session that allows our clients to feel relaxed and not rushed so that we can get natural expressions and lots of variety for them.
8. What happens after the session?
Your experience doesn’t end when the camera is put down. Ask:
- When you’ll see your images
- How image selection works
- Whether help is provided choosing favorites
- What formats and resolutions are included
- How are images delivered
- Is there any assistance available for sizing and usage questions
Decision fatigue is real… a streamlined, guided process makes the experience more enjoyable and definitely less overwhelming.
Final Thoughts
A great headshot session is about more than getting “a decent photo.”
It’s about creating images that help you show up confidently in your business and career, with an experience that feels easy from start to finish.
We believe that the best portraits happen when clients feel guided, comfortable, and genuinely seen. Whether you need a polished professional headshot or a full branding session, the goal is always the same – authentic images you will be proud to use, with an effortless experience.
Let’s plan something amazing together.
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