How to Get the Most Out of Your Personal Branding Session: Why Your Headshot Matters More Than You Think

If you’ve been putting off updating your headshot for the last two, three, or (be honest) five years, you are not alone. I hear it from entrepreneurs, founders, and creatives all the time: the business has grown, the brand has evolved, but the photo on the website is still the one from a coffee shop selfie session back when the company was just an idea. A personal branding session is one of the best investments you can make in your business, and I want to walk you through exactly how to prepare so the day feels easy, low pressure, and the images actually feel like you.

Your headshot is often the very first impression a potential client, collaborator, or investor has of you, long before they hear your voice or read your bio. It sets the tone for how people perceive your professionalism, your personality, and whether they trust you enough to click “contact” or “book a call.” A great branding photo does more than look polished. It communicates who you are and what it might feel like to work with you.

Think about the last time you scrolled through a website or LinkedIn profile and stopped on someone’s photo. What made you pause? Usually it’s not perfection. It’s warmth, confidence, or a sense that this is a real person you’d enjoy talking to. That’s what we’re after together.

Start With the Story You Want to Tell

Before we even get to camera settings or locations, I always ask my clients: what do you want someone to feel when they see this photo? Are you the warm, approachable expert? The bold, confident leader? The creative who thinks outside the box? The steady, trustworthy advisor? There’s no wrong answer, but knowing your answer helps me choose light, posing, and location that supports it rather than fights against it.

It also helps to think about where these photos will actually live. A speaker bio page, a homepage hero image, a press kit, and an Instagram grid can all call for slightly different energy, even if they come from the same session. We don’t need to overthink this ahead of time, but having even a loose sense of your priorities helps me plan our time together so nothing important gets missed.

Wardrobe Tips That Actually Help

Wardrobe is one of the biggest factors in how a branding photo reads, and it’s also where I get the most questions. A few things I always recommend:

Choose solid colors or subtle textures over busy patterns, small checks, or fine stripes, which can distract from your face and sometimes create a strange visual effect on camera called moiré. Solid jewel tones, soft neutrals, and classic navy or black all photograph beautifully and tend to age well, meaning your photos won’t feel dated in a year or two.

Bring two or three outfit options so we have room to adjust if the first look isn’t reading the way we hoped once we see it on camera. A blazer over a simple top, a swap of a necklace, or rolled sleeves can completely change the feel of a shot without requiring a full outfit change.

Wear something that feels like you on a great day, not a costume of who you think you should be. If your brand has signature colors, weaving one in subtly through a top, an accessory, or even a manicure is a lovely touch, but it should never overpower the photo or compete with your face.

Steam or iron everything the night before, and bring a small kit with you on the day just in case. Wrinkles are far more noticeable through a camera lens than they are in the mirror.

If you’ll be photographed from the waist up for most shots, it’s still worth dressing fully and wearing real shoes. It changes your posture and how you carry yourself, even if your shoes never make it into frame.

Hair, Makeup, and the Little Details

You don’t need a full glam team unless that’s part of your vision, but a few small touches go a long way. Fresh haircuts should happen at least a week before your session so the cut has time to settle. If you wear makeup day to day, apply it slightly more than you would for the office, since camera flash and natural light can both soften color and definition. Matte finishes generally photograph better than heavy shimmer, which can catch the light unexpectedly.

If professional hair and makeup is available in your area and fits your budget, it can be a wonderful way to feel taken care of on the day and to free up your energy for the actual photos rather than last-minute touch-ups. Let me know if you would like my recommendations for a hair and makeup artist. I know many who do an amazing job and I’ve personally had the privilege of working with over the last 17 years.

Location Sets the Mood

Some entrepreneurs want the clean, timeless simplicity of a studio backdrop. Others want their actual workspace, a favorite café, a bookstore, a garden, or an outdoor setting that reflects their personality or industry. I love helping clients think through this because the right backdrop can add so much dimension to a branding shoot without competing with you as the subject.

If you’re torn, tell me about your ideal client and what you want them to feel when they land on your site. That usually points us toward the right setting. A wellness coach might want soft natural light and greenery. A financial advisor might want clean architectural lines. A chef might want their own kitchen. There’s no formula, but there is usually an instinct, and I love helping you follow it.

Consider mixing locations, too. We might start in one setting for your more polished, formal shots and move somewhere with different light or texture for a second look. This gives you a wider range of images to pull from later.

Timing and Light

If we’re doing your branding photos or headshots outdoors, timing matters more than most people expect. Early morning and late afternoon light is soft, flattering, and far more forgiving than the harsh midday sun. If your schedule allows flexibility, I’ll always guide you toward the time of day that will give us the best light for your particular location.

I prefer doing most branding sessions in studios. I try and find studios with lots of options for props and different backdrops to help give your portfolio diversity.

Bring a Playlist and a Little Movement

The stiff, arms-crossed corporate headshot is not the only option anymore, and to be honest, it’s rarely the most compelling one. I love working in some movements, genuine laughter, and candid in-between moments alongside the classic polished shots. Walking toward the camera, a natural laugh between shots, or simply looking away and back again can produce some of the most authentic images of the whole session.

Bringing a favorite playlist, a mantra, or even just a funny memory to think about during the session helps loosen you up in front of the camera, and it shows in the final images. I’ll also be talking with you throughout, asking questions and keeping the mood light, so you’re rarely just standing there waiting to be told what to do.

Come With a Shot List, But Hold It Loosely

It helps me enormously if you know ahead of time where these images will live. Website hero image, LinkedIn, Instagram grid, press features, a book jacket, printed marketing materials. Each of those has slightly different framing needs, and letting me know in advance means we can plan for it during the session rather than realizing afterward that we’re missing a vertical crop or a wide environmental shot with room for text overlay.

That said, some of the very best images come from unplanned moments, so we’ll always leave room to follow what feels natural too. I’d rather hand you a gallery full of options than a rigid checklist that leaves no room for spontaneity.

Think About Props and Context Clues

If there are tools of your trade that feel meaningful, a favorite notebook, a camera, a musical instrument, ingredients if you’re a chef, don’t hesitate to bring them along. Used sparingly, these details can add authenticity and context without turning the photo into a prop shot. The goal is always for you to remain the focus. Before your session, we will hop on a call or email and go over some ideas you and I come up with for specific poses and photos that will be beneficial to your business.

Give Yourself Grace on the Day

Feeling a little nervous in front of the camera is completely normal, even for people who present in front of rooms full of people for a living. Trust me, I have been there myself. Which is why my job is to help you feel comfortable, guide you through posing that feels natural rather than forced, and create a space where you can just be yourself. The more relaxed and present you are, the more the photos will reflect the version of you that your clients fall in love with.

I’ll never leave you standing stiffly wondering what to do with your hands at your brand session. We’ll move through a variety of poses, moves and expressions together. I’ll show you along the way so you can see what’s working and relax into each pose.

After the Session

Once we wrap, I’ll walk you through what to expect for turnaround time and how your images will be delivered. I always recommend choosing a handful of favorites for immediate use, like your top LinkedIn photo or website hero shot, while taking your time to go through the full gallery for everything else. Your new images can also become the foundation for a broader content library, giving you a bank of authentic, on-brand photos to pull from for months of marketing rather than searching for a new photo every time you need one.

If you’re ready to update your branding photos and want images that feel as intentional and authentic as the business you’ve built, I would love to help. Reach out through my contact page and let’s talk about what story you want your next set of photos to tell.