How to Choose the Right Headshot Photographer

Choosing a headshot photographer can be daunting. A simple search for “Denver headshot photographer” brings up a lot of results, and a lot of choices. But who do you pick, and how do you choose.

A great headshot should make people want to engage with you, on LinkedIn, your company website, or anywhere your professional image shows up. The right photographer doesn’t just take a picture. They guide you, ask how the headshot will be used, and help you look like the best version of yourself.

I spent over 20 years working in the corporate world before specializing in professional headshots. I’ve seen firsthand what works, what doesn’t, and why so many people walk away unhappy with their photos. If you’re deciding who to trust with your headshot, here are the most important things to look for.

Choose a Photographer Who Knows How to Put You at Ease

Most people don’t enjoy being photographed. Actually, nearly everyone doesn’t like being in front of the lens. Unless you’re a model, actor, or influencer or really do thrive being in the limelight that feeling awkward, stiff, or unsure of what to do with your face or body is incredibly common.

That’s why the single most important quality in a headshot photographer is the ability to make you feel comfortable, and clearly guided, in front of the camera.

An experienced headshot photographer should guide you through posing and facial expression step by step, never leaving you guessing what to do. Clear direction creates confidence, and confidence is what people respond to when they see your headshot. The goal is a professional image that feels approachable, natural, and authentic, not forced or over-posed.

Make Sure They Understand Your Career and Your Goals

If a photographer doesn’t ask what you do, who you’re trying to reach, or where you want your career to go, that’s a photographer who’s just pushing the shutter button.

Your photographer should understand why the image you project matters and how it can influence first impressions. Whether you’re a lawyer, a tech executive, a healthcare professional, or an entrepreneur, your headshot should still look like you and reflect your industry appropriately.

The best headshots are created with intention, not guesswork.

Avoid the “Stand There and Smile” Experience

One big mistake people make when choosing a headshot photographer is settling for someone who simply places them in front of a backdrop, takes a few photos, and sends an online gallery later.

When there’s little direction and no conversation, the results are hit or miss. You’re left hoping there’s at least one usable image. That’s not a great position to be in when your professional reputation is on the line. Not to mention the time and effort to schedule your headshot.

A strong headshot session should feel collaborative and guided from start to finish.

If you hate having your photo taken, you’re not alone, and the right photographer can completely change that experience.

Pay Attention to the Experience, Not Just the Portfolio

I often hear clients say their previous headshot experience felt rushed or impersonal, but that they actually enjoyed their time in front of my camera. Some even say it was fun.

In many cases, their previous headshot was done quickly by a photographer their company hired that didn’t engage with them while their photo was taken. They didn’t get to see the images, choose their favorite, or make small adjustments to improve the result. That lack of involvement can make people feel disconnected from their own image.

A good photographer builds the experience around you, not around speed alone.

Look for a Clear, Professional Process

A photographer’s process tells you a lot about the quality of their work.

When someone contacts me, I ask how the headshot will be used, LinkedIn, a company website, speaking engagements, or simply updating an outdated photo. Based on that, I recommend the session that best fits their needs. I also offer wardrobe guidance and professional makeup as an option, because preparation plays a huge role in the final result.

Background, lighting, and consistency matter too, especially for companies. Most clients choose classic grey or white backgrounds, but I also offer different backgrounds that help make headshots pop. It all depends on the look you or your company are going for. If you want to see how this approach translates into real sessions, you can learn more about my professional headshot services here.

Most importantly, my clients review their images before they leave. They select their favorites on the spot, and if something feels slightly off, expression, hair, or pose, we make adjustments and shoot more until it’s right.

Your headshot should be a photo you’re happy to show.

Ask About Real-World Results, Not Just Pretty Photos

I’ve worked with many clients who were hesitant to update their headshots because they liked their old one, often taken years ago. In reality, they were attached to a version of themselves that no longer reflected who they are today.

Almost without exception, those clients are pleasantly surprised by their new images. While it can take a moment to adjust to seeing a more current version of yourself, a professional headshot should feel authentic and honest. The goal isn’t to look younger, it’s to look confident, credible, and approachable right now.

For Companies, Consistency and Efficiency Matter

For team and company headshots, consistency is everything.

When your employees are across the country having a cohesive and consistent look adds to the reputation and brand of your company. A good photographer will be able to create headshots that have the same consistent look and feel for employees whether they all work in the same building or live on either coast or everywhere in between.

Being efficient is also important. National conferences tend to have a lot of attendees, and their days are usually packed with meetings and seminars. It’s important your photographer is able to work with your schedule and get the most number of headshots done with the time frame available. I often work with tight schedules, but I am still able to give attention to each person coming through and create headshots they are happy with.

When teams look cohesive and professional, it reflects directly on the brand.

A Good Photographer Helps Ensure Your Image Looks Professional

Your headshot should reflect your professionalism and your personality. Your photographer should help guide you through the process.

I offer pre-consultations for my higher tier sessions, and even during shorter sessions I take time to discuss wardrobe and usage. In one instance, I suggested a client reschedule because the outfit they brought didn’t align at all with the professional image they wanted to project. It wasn’t the easiest conversation, but it was the right one.

A photographer who truly cares about your outcome will help you make those decisions, even when it’s inconvenient.

Think About Value, Not Just Price

Experience, guidance, and consistency matter, especially when your headshot represents your career or your company.

Less experienced photographers may rely on minimal lighting setups, limited direction, and quick turnaround galleries. That can leave you hoping at least one photo taken works. A professional headshot session should remove that uncertainty and give you confidence in the result.

The Most Important Advice I Can Give

Even if you don’t hire me, make sure you feel comfortable with the photographer you choose.

If you feel awkward or uneasy during the session, it will show in your photos. When you feel relaxed, supported, and guided, it comes through immediately. Your headshot should make people want to connect with you, and that starts with how you feel in front of the camera.

If you’re considering updating your headshot and want a guided, professional experience, I’d be happy to help. A great headshot isn’t just a photo, it’s an investment in how you show up.