How to Plan a Successful Personal Brand Photoshoot (+ behind the scenes of mine)

When your business is your personal brand, you’ll need to know what it takes to have a successful personal brand photoshoot. There’s good reason why I’ve written a lot about getting the best headshots for your website.

The photos on your website really can make or break your online presence.

And as a web designer when a client provides me with less than par photos to use, it makes building their website a lot more difficult. Difficult in the sense that they’re the face of their brand but we use their face sparingly due to the quality of photos.

Stock photos have their place but I really encourage my clients to get different poses, outfits, and shots of themselves to use creatively on their website.

While most of my clients come to me with their personal brand photoshoot complete and files ready to go… there’s a fair amount of clients who come to me for advice on getting the best photos for their new brand and website.

And while I’ve touched on this topic before, I want to approach it today from a different angle.

Today we’re going to discuss how to plan for your next personal brand photoshoot while giving you a behind-the-scenes look at my most recent headshot session.

Since starting my first business about 9 years ago I’ve had a total of five different personal brand photoshoots for my brand. For my business, it’s vital for my headshots to look like me. So if I change my hair, get new glasses or change my appearance in some other way then I’m going to need updated headshots.

Another reason to get new headshots is if your business is headed in a new direction or you’re trying to attract a different clientele.

The reason I’ve been through 5 professional photoshoots for my business is a combination of those issues.

Here are a few of those headshots and the reasoning why I’m not using them today.

Headshot Session 1: Outdated

In 2011 I was coaching successful (yet overwhelmed) mom entrepreneurs. Helping them simplify their life and business. These are excellent photos but outdated as I’m no longer coaching. They have a totally different vibe than my business today. Not to mention I had bangs…

Headshot Ideas for Website Designer, Personal Branding
Photos by Alimond Studio in Leesburg, Virginia

Headshot Session 2: Too entry-level

In early 2016 I took a major pivot in my life and business. I had recently pressed pause on coaching and began designing websites. I was working primarily with new entrepreneurs with small budgets. They were also pretty intimidated by tech. I felt passionate about simplifying this for them. Most of these clients were just getting started and needed an entry-level site. 

While I like these pictures, I feel they’re a bit entry-level. Today, I create elevated branding + websites for interior designers so I’m certainly not going to use photos I feel position me as entry-level.

Headshot Ideas for Personal Brand
Photos by Tiptoe Studio in Charles Town, West Virginia

Headshot Session 3: Outdated, not enough variety

By 2018 my web design business was strong and stable. I had niched down and wanted to attract more established business owners. At the same time, I wanted to have a relaxed vibe. My hair was much longer, too. So I booked a new session to update my website accordingly. The problem here was that I cut my hair and got different glasses a few months later. Bad planning on my part…

Web Designer Minimalist Personal Brand Photoshoot
Photos by Alimond Studio in Leesburg, Virginia

Headshot Session 4: Too “casual”

In 2019 the only real reason I got new headshots was for the reasons mentioned above. I cut my hair much shorter and got new glasses. I also went through a phase where I’d curl my naturally pin-straight hair each morning… so there was that, too. I was happy with the below shots as they were professional yet friendly. However, I got smart and learned to embrace my straight hair… which meant I wasn’t showing up on Zoom calls with curly hair.

I could have probably lived with the hair issue but the more I looked at these photos the more they felt like “Hi, I’m nice… want to be friends? Let’s go laugh together.” When I really needed photos on my website that said “Hi, I’m a professional who is established in my field, known for creating stellar (strategic) brands and websites and I can help you, too. I’m also nice and we might laugh a bit together.” So the positioning with these were a bit off-brand.

Friendly Professional Personal Brand Photoshoot
Photos by Tiptoe Studio in Charles Town, West Virginia

Headshot Session 5: Just right!

At the beginning of 2020, I told myself I’d gift myself with updated headshots with my favorite headshot photographer. So I started a secret Pinterest board with inspiration for that perfect shoot.

When I felt ready, I booked my shoot and started to prep for the day. I made sure I communicated to my photographer I wanted my photos to be high-end, polished, professional, position me as the expert yet remain approachable.

High-End Polished Personal Brand Photoshoot for Web Designer for Interior Design Studios
Photos by Alimond Studio in Leesburg, Virginia

I think it’s safe to say that we nailed it this time around.

But that’s only because there was lots of strategic planning on my end before the day of the shoot.

I want to help you plan for your next shoot so it’s just as successful.

I want to be clear the biggest reason the previous headshots didn’t work was me. It had nothing to do with the photographers. They did their job and did it well. I simply didn’t plan well enough for them to work for my brand long-term.

With that being said, let’s go step by step on how to plan for your next shoot so it does work long-term.

Step 1: Get on Pinterest and start pinning the looks you’re after.

Think of this first step as a brain dump. You can start pinning from this board and then once you have a few, go to your board and click More Ideas. Pinterest will automatically curate similar photos for your liking.

Step 2: Identify your vibe.

Open a Google Doc and brain dump the vibe you’re after. Is it professional yet friendly, cheerful and fun, corporate professional? Write all the attributes that come to mind when you’re considering your brand, your ideal client, and how you want to show up in the world.

After you write everything that comes to mind, narrow it down to one sentence. Mine was narrowed down to the following: high-end, polished, professional, expert, approachable. 

Step 3: Outline your site.

For this step, you want a really rough draft of your site outline. Simply put, you want to know what pages you’ll need photos for. But diving deeper, you’ll want to know the vibe of that page. This will give you clarity on the type of photos you’ll need.  Here are a few examples I outlined before my photoshoot:

  1. Home Page – powerful leader but approachable
  2. About Page – friendly, fun
  3. Services – professional, expert
  4. Testimonials – humbled, grateful
  5. Blog – pose with a laptop
  6. Contact – ready, inviting

You can see that if I only had a Pinterest board without this added clarity, I might not get what I need from my headshot session. With this outline, I can now pinpoint the exact photos I need plus how they’ll be used.

You’ll notice this also allows for some flexibility for me and the photographer. I’m not listing the exact pose or outfit or smile… I’m just jotting down the vibe I’m after. A great photographer will see these attributes and help you capture them in a variety of ways.

Step 4: Go outfit shopping!

I’ll be the first to tell you, I don’t like shopping. And I really don’t like clothes shopping. So to make this task simpler, I jumped back on Pinterest and created a new section on my board called “Outfits.” Just as I did in Step 1, I started pinning all the outfits that I thought would be suitable for my photos. This gives me a starting point for planning my outfits.

After I’ve established my look, I start in my closet. You might have noticed in the headshots shared above there is one staple piece I always gravitate towards. My white blazer. It’s timeless and really goes with so much. Then I went on Amazon to find a few more pieces. And lastly, I visited the outlet mall to wrap up the rest.

I’m not one to wear a lot of jewelry or accessories but made sure to bring some timeless necklaces and a belt.

When I arrived at my session, I told my photographer I have the outfits but I’d needed her help on the poses and when to wear what during the session… which she totally rocked guiding me through.

For color, I always recommend staying neutral. Take a peek at this board of headshots, what do you notice about their outfits? They’re basically all in neutral colors. This doesn’t mean that your brand and website can’t have pops of color but for your headshots, it’s best to stay neutral. In fact, it’s actually easier to invite in color to your brand when your headshots aren’t busy with color. 

Step 5: Arrive prepared.

The day before my shoot I made sure to drink lots of water and not stay up too late. Then that morning, I showered and did my hair and makeup like I would if I was headed to a client meeting (in-person). With that said, I only meet with clients via Zoom but pretended I was going to meet them in person.

When doing your hair and makeup, you should go after the most polished version of yourself.

Some clients like to get their hair and makeup done, which is a great idea if you’re feeling stressed about getting prepared yourself. Just make sure they’re able to capture your typical look.

I also made sure to pack up my iPads and laptop. While I actually work at my desk on a large iMac, I borrowed our family laptop and kids’ iPad to use for props.

Step 6: Relax and let your photographer take the lead.

I really can’t stress the importance of having a rockstar photographer take your photos. I invested thousands of dollars to work specifically with Aliyah at Alimond Photography. Reason being? This is her specialty. She told me when to smile, where to tilt my chin, when to change my outfit, when to fix my hair. The day of, I trusted her to be the expert she is. The result? I got the exact photos I needed to polish my online brand and website.

Here are the end results:

If you’re in the Northern Virginia/DC Metro area, I highly recommend booking a session with Aliyah Dastour from Alimond Studio. If you’re not, I’d recommend looking for a studio or photographer that specializes in headshots for entrepreneurs.

As a seasoned brand and website designer, Katie O'Brien strives to bring simplicity to business growth and peace of mind to daily life. Specializing in timeless brands and impactful websites, she works closely with interior designers elevating their digital homes with poise and personality.

Explore More Articles:

My Step-by-Step Brand and Website Design Process

My Step-by-Step Brand and Website Design Process


Hiring a Web Designer? FAQs for Everything You Want to Know

Marie Forleo BSchool 2023 Overview

An Overview of Marie Forleo’s BSchool in 2023

My B-School Review on Marie Forleo's B-School Online Course

Thinking About Marie Forleo’s B-School? Here’s My Review