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LIFE THROUGH THE LENS
Photographic Journey with Cary Pennington

How to Nail Your Business Headshot: The Ultimate Preparation Guide

  • Mar 15
  • 6 min read

Updated: 5 days ago

Man in a black suit and light blue shirt against a black background, looking confidently at the camera.

A professional headshot is more than just a photo. It’s your first impression, your personal brand, and a key part of your online presence. A polished headshot is crucial in today's digital age.


Whether updating your LinkedIn profile, enhancing your website, or refining your company bio, presenting yourself professionally is crucial. This helps in making a strong impact. A well-crafted headshot communicates confidence, approachability, and professionalism, setting the tone for how others perceive you in your professional endeavors. In this comprehensive guide, we will walk you through everything you need to know to prepare for your business headshot session.


From selecting the right photographer who understands the nuances of professional imagery to choosing the ideal location that complements your personal brand. Every detail matters. We will cover essential aspects such as wardrobe choices that align with your industry and personal style, as well as tips for grooming and makeup to ensure you look your best on camera.


Additionally, we will discuss the importance of posture and facial expressions. We will provide techniques to help you feel relaxed and confident during the shoot. Understanding how to engage with the camera can make a significant difference in the final outcome of your headshot.


Furthermore, we will explore the significance of lighting and background selections, which play a pivotal role in enhancing the overall quality and impact of your photograph. By the end of this guide, you will be fully equipped with the knowledge and tools necessary to approach your headshot session with confidence, ensuring that you not only look your best but also feel empowered to showcase your personal and professional brand effectively.


A great headshot is a powerful investment in your future, and with the right preparation, you can create an image that resonates with your audience and leaves a lasting impression.



Woman with blonde hair and pink lipstick in a dark jacket and green top against a gray background, looking confidently at the camera.

How to Choose the Right Headshot Photographer

Selecting the right headshot photographer is an important decision that requires thoughtful consideration. Just like any other service, the quality of headshots can vary significantly—from outstanding to mediocre to subpar. A professional headshot should look great and consistently reflect your personality. Here are key factors to consider when choosing a professional headshot photographer:


1. Review Their Portfolio

Take the time to explore the photographer’s portfolio on their website and social media platforms. Look for consistency in style and quality. Do the images stand out? Do the subjects appear natural and confident? Avoid overly retouched photos—skin should have texture, and the image should still look like the person in real life.


2. Specialization Matters

Choose a photographer who specializes in headshots. While a newborn or landscape photographer may take great pictures, headshot photography requires a unique skill set. Just as you wouldn’t visit a pediatrician for an adult check-up, it’s best to work with a professional who has honed their expertise in capturing compelling headshots.


3. Read Client Reviews

Client testimonials can provide valuable insight into a photographer’s reliability and professionalism. Look for consistent positive feedback, especially regarding image quality, turnaround time, and overall experience. Be mindful of any red flags, such as missed deadlines or poor communication.


4. Communication & Response Time

Timely communication is essential. A professional photographer should respond promptly to inquiries—ideally within 12 hours. A photographer who values responsiveness from the start is more likely to provide a smooth and efficient experience. We typically respond within 2 hours.


5. Understand Pricing & Packages

Make sure you understand the pricing structure before booking. Some studios charge a session fee with additional costs per image, while others offer all-inclusive packages. Clarify what’s included—such as retouching, outfit changes, and digital files—so there are no surprises later.


By carefully considering these factors, you can confidently choose a headshot photographer who will provide a great experience and deliver professional results.


Man with curly hair in a suit and purple tie, standing against a dark gray background, looking confidently at the camera.

Headshot Preparation Guide

1. Define Your Purpose

Before your session, consider how you wish to be perceived by your audience. Decide if you want a polished corporate look with tailored suits and classic colors for authority, or a friendly vibe with softer colors and casual attire for approachability.


Alternatively, if you're in a creative field, consider unique patterns and bold colors to express innovation. Your industry influences your style—corporate finance might prefer traditional looks, while tech or creative fields allow more freedom.


Align your style with your personal brand and the context of the photo's use, whether it's for a website, social media, or marketing. Thoughtful consideration of these elements ensures a cohesive image that communicates your message effectively.


Questions to Ask Yourself:

  • Where will I be using this headshot? (LinkedIn, website, press release, etc.)

  • What message do I want my image to convey? (Confidence, warmth, leadership?)

  • Does my industry lean toward formal or casual attire?


Man in a blue suit and tie smiles slightly against a dark background, conveying professionalism and confidence.

2. Choose the Right Outfit

Your wardrobe is a crucial part of your headshot. Here’s what to consider:


General Guidelines:

Stick with solid colors or subtle patterns—bold prints can be distracting. Neutral tones like navy, gray, black, and white work well for a professional look. Avoid busy patterns or logos (unless it's part of your brand).

If you wear glasses daily, bring them—but ensure they are glare-free.

If you’re unsure, bring multiple outfits for variety.


For Men:

  • A well-fitted suit or blazer with a dress shirt (tie optional based on industry).

  • Avoid overly bright colors—stick with classic tones for timelessness.

  • Make sure your clothing is pressed and lint-free.


For Women:

  • A blazer or structured top that flatters your shape.

  • Minimal jewelry to keep the focus on your face.

  • Consider necklines that frame the face well—avoid deep V-necks or distracting cuts.

  • Stick with natural or professional makeup (avoid heavy contouring or glitter).




3. Grooming & Hair Prep

Looking polished is key, but you still want to look like yourself. A little preparation goes a long way.

✔ Get a haircut or trim a week before your session to allow it to settle.

✔ Style your hair naturally; avoid drastic changes right before the shoot.

✔ Consider professional makeup for a polished but natural look.

✔ Men: Shave or groom your beard neatly before the session.

✔ Stay hydrated to keep your skin looking fresh and radiant.

✔ Avoid excessive tanning or trying new skincare treatments right before your shoot.


Smiling woman with arms crossed, wearing a white shirt, stands against a plain light background, exuding confidence and warmth.

Smiling woman with long dark hair, wearing a white shirt, against a gray background. Her expression is friendly and warm.

4. Posing & Expression Tips

Not a model? No problem! A professional photographer will guide you, but here are a few tips to feel confident:

✔ Keep a relaxed but upright posture.

✔ Slightly angle your body for a natural look—straight-on shots can appear stiff.

✔ Think about something that makes you happy for a genuine smile.

✔ Experiment with slight head tilts to find your best angle.

✔ Relax your shoulders to avoid tension in the shot.



5. The Day of the Shoot

What to Bring:

✔ A couple of outfit options

✔ Makeup or touch-up items (powder, lipstick, hairbrush)

✔ A lint roller to remove any stray fibers

✔ Confidence and a great attitude!


What to Avoid:

✔ Rushing—arrive on time to feel relaxed.

✔ Heavy meals right before the shoot (to avoid bloating).

✔ Drinking too much caffeine (to prevent jitters).

✔ Overthinking—it’s okay to have fun with it!


6. Post-Shoot & Image Selection

After your session, your photographer will provide proofs for you to choose from. Keep in mind:

✔ Select images where you look confident and approachable.

✔ Consider the different platforms you’ll use them for.

✔ Opt for light retouching to maintain a natural look.

✔ Get both high-resolution and web-friendly versions for versatility.


Smiling man in a blue checkered shirt and dark blazer, standing against a dark, neutral background.

7. The Benefits of Choosing a Local Photographer

Supporting local businesses is a great way to give back to your community. Choosing a nearby photo studio provides convenience and the opportunity to establish a lasting relationship with your photographer.

If you have a dependable headshot photographer in your area, you're in luck! Forming a connection with a local professional ensures consistency in your branding and simplifies updating your headshot when needed.

Keeping your headshot up-to-date is crucial—at least once a year. Your professional image should always reflect your real-life appearance, maintaining your credibility in face-to-face meetings. If you change your hairstyle, hair color, facial hair, or make any other significant alterations to your look, it's an ideal time for a new headshot.


Final Thoughts

Preparing for your business headshot session doesn’t have to be stressful. With the right preparation, you can ensure your photos reflect both your professionalism and personality. A great headshot is an investment in your personal brand, so take the time to prepare and make the most of your session!

Ready to make your image stand out? Book your professional headshot session today! Contact me today to book your session.


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Cary Pennington Photography, the best headshot photographer in Carlsbad, is based in Carlsbad, CA, and proudly serves clients throughout San Diego County and Orange County. We specialize in professional headshots and personal branding photography for entrepreneurs, executives, real estate agents, business coaches, corporate teams, and professionals across various industries. Whether you're looking to elevate your brand, refresh your LinkedIn profile, or create a polished, professional image, we provide high-quality headshots tailored to your unique style and industry needs.

Cary Pennington Photography goes beyond traditional headshots, offering dynamic acting headshots, impactful corporate events, and product branding images that make a lasting impression. In addition to professional branding photography, Cary specializes in beautiful family portraits and high-end food photography, crafting visually striking images for restaurants, chefs, food brands, bloggers, and publications. With a sharp eye for detail and a creative approach, Cary transforms moments and culinary artistry into compelling, high-quality visuals.

Serving San Diego including North County San Diego, La Jolla, Del Mar, Carmel Valley, Solana Beach, Rancho Santa Fe, Rancho Bernardo, Poway, San Elijo Hills, Escondido, Encinitas, Cardiff by the Sea, La Costa, Carlsbad, Oceanside, Vista and San Marcos.

© 2005-2025 by Cary Pennington Photography based in San Diego, California. All Rights Reserved.

Any use of images without written permission prohibited.

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