Not Your Average Headshot: Frequently Asked Questions

April 30, 2025

Let’s be honest—headshots have evolved beyond those awkward yearbook-style poses and stuffy corporate backdrops. But I still get a ton of questions and comments (like a lot!) about everything from what to wear to ‘I hate having my photo taken.’ Whether you’re booking your very first session or it’s just time for a refresh, I’m here to make the process simple, relaxed, and dare I say… even fun.

As a Kitchener-Waterloo headshot and branding photographer, I’ve worked with hundreds of professionals, creatives, and entrepreneurs across Cambridge, Waterloo, Guelph and the surrounding KW region. And trust me—these are the headshot questions I hear time and again.

1. What should I wear for a headshot?

Stick with solid colours and clothing that feels like you—confident, put together, and comfortable. Neutrals and soft tones are always a win, but if you’ve got a pop of colour that fits your brand, bring it! Avoid logos and busy patterns that are distracting. Not sure what to choose? Feel free to bring a backup outfit. I’m always happy to weigh in.

When you book, you’ll also receive a helpful prep guide to make sure you feel fully ready and confident walking into your session!

2. What do I do with my hands?!

The million-dollar question! You’re not alone—I will guide you every step of the way, including what to do with your hands. I’ll give you easy prompts and direction to help you look relaxed, confident, and totally natural. I even wrote an entire blog post on this exact topic—check it out here!

3. How soon will I get my gallery?

You’ll receive your fully edited gallery within a week of your session—often sooner, but one week max! In a rush (hello, last-minute LinkedIn updates 👋)? Express editing is available for a small fee, with your gallery ready within 24 hours.

4. Do you retouch the photos?

Yes! Every final image gets a polished, professional edit—think clean, refined, and natural. I remove small blemishes, whiten eyes and teeth a touch, and give you that “rested and confident” look we all want in a headshot.

5. How long does the session take?

My headshot sessions are short and efficient—about 20 minutes for my most popular Essential Headshot Session. You’ll be surprised how much we can accomplish in that time! Want more variety or multiple outfits? My one-hour Signature Session gives you more flexibility and space to play with different looks.

6. Where do headshot sessions take place?

I’m known for my modern, environmental-style portraits—think natural light, clean lines, and real-world backdrops that feel fresh and on-brand. I love using modern buildings, textured walls, or even quiet urban corners throughout Kitchener, Waterloo, and Cambridge that elevate your headshot without feeling too “corporate.”

That said, if you prefer a classic studio-style look, I’ve got you covered there too! I have portable backdrops and studio lighting, plus access to professional studio spaces across the KW region for a clean, polished finish.

7. What if I hate having my photo taken?

You are so not alone in that. Most of my clients tell me they’re awkward in front of the camera—then leave saying it was way more relaxed than they expected. At Portraits by Kendra, I keep it easygoing and fun, and I promise to guide you every step of the way, so you never feel stiff or unsure.

8. What’s included in your headshot packages?

Each session includes your session fee, your final retouched images, and the option to purchase additional ones if you love more than you expected (it happens more than you think!). I also offer discounted headshot packages for teams and full corporate branding photography packages if you’re looking for a deeper content refresh with lifestyle images, behind-the-scenes moments, and more.

9. What’s the difference between a headshot session and a branding session?

A headshot session is all about you—typically from the shoulders up (though I do love a great 3/4 pose too!). It’s simple, professional, and perfect for LinkedIn, your website bio, or speaking engagements. It’s focused, efficient, and designed to give you a strong, polished first impression.

A branding session goes deeper. It’s for entrepreneurs, creatives, and professionals who want to tell a bigger story. Think lifestyle images, candid behind-the-scenes shots, multiple locations or outfits, and content you can use across your website, social media, and marketing materials. It’s still fun and relaxed—but way more personalized and strategic.

10. Do you offer team or staff headshots?

I do! I work with businesses and organizations of all sizes to create polished, professional headshots. And if you’re looking for a relaxed, efficient way to update your whole team—Corporate Portrait Parties are where it’s at.

It’s a little bit like school portrait day… but for your workplace. And trust me—it’s way more fun. I bring the setup to you, we keep things moving, and everyone walks away with a fresh new headshot that actually feels like them. Find out more about it on the blog.