You may have hundreds of reasons why you don’t need professional photography for your business. You have a fancy camera attached to your phone. Your kid has Photoshop. Besides, what really matters is how well you do your job and since you’re not a photographer, it really doesn’t matter that much, right?

No. No, that’s not right.

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Everything you put out into the world with your name / your business name on it is a reflection of the work you do. Even if that bit is not something you do for business - it’s an expression of you and your business. A crappy website tells people that you’re not taking your work seriously. A typo in your content or your newsletter tells people that you don’t care enough about details. And an amateur photo? It makes you look - quite literally - like an amateur.

Have a quick look through your LinkedIn contacts. How many photos look like they were taken socially (rather than professionally), with the background poorly cut out of the photo? What are your first thoughts when you see these? We’re going to bet they’re not complimentary.

We interviewed the fabulous Jessica Venturi, professional business and fashion photographer, to find out what you need to know to in order to find a great photographer and look amazing in your headshots.

I don’t need a headshot.


If you are going to hire someone for any job, you are going to Google them. You will do your research, and determine if this is someone that you connect with. People want to get a feel for the person they’re going to work with ahead of time. No one wants to go in blind. If you don’t provide your prospective customers with the opportunity to look at and understand you, they will take their business to someone who does.

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What Makes A Good Headshot?

Headshots have changed a lot since the days where you sat down in a studio with a standard dark blue backdrop, hands on your lap. Now, a good headshot shows your personality a bit more. It may be a little looser, but still professional. Of course, it must be well-lit, and retouched!

Remember to actively look into the lens of a camera. Your photo must connect with the viewer. I see far too many headshots where the subject is looking just slightly off-camera. There’s something off-putting about that, as though the person is a bit shifty, that they’re hiding something. You don’t quite know why, but for some reason, you just don’t trust that person.

Jessica said this shot of Admin Slayer CEO, Julia Chung, is actually okay even though she’s not looking at the camera, because it shows “personality”.

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Can You Really Make a Connection in a Photo?

YES! This might be the very first time a person “sees” you. You want them to immediately feel engaged with you, and looking the camera right in the lens is one of the first ways to do that. You want to appear trustworthy and competent. Your photo is your calling card, representing who you are (or want to be), and how you want to be seen. The photo should say that you know how to do your job - a shitty photo says you just don’t know what you’re doing.

All businesses are based on relationships. If there are twenty people that I can choose from to do your job, am I going to pick the person I have no connection with, and no feeling for who they are or what they do? If I came to your office and you were wearing something entirely inappropriate to your job - for example if a professional (where the uniform is a suit) was wearing a pair of sweatpants I would be horrified. What have I done hiring this slovenly human? It’s a reflection of what you do, and your photo matters just as much as your in-person appearance.

How Do We Determine if a Photographer is “Good”?

(For those of us who are not photographers, or perhaps don’t really have an eye for this kind of art, how do we have any idea who is good at this?) The best way is to look at their portfolio. Look for quality shots - especially for good lighting. Review the headshots they’ve taken. Do the people in those photos look the way you would want to look? Is the photo well retouched - does their skin look healthy? Real skin is a big deal. You don’t want to look like a plastic doll.

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How is the lighting? A badly-lit photo has shadows in all the wrong places. Look into the shadows. Are there lines on their face from the light being from the wrong direction? Is the photo unusually bright or unusually dark?

Once you review the photos, you’ll start to realize that in some photos, people look as though they are live, vibrant - almost as though they are in-person, in front of you, and about to start a conversation. That’s the mark of a great headshot.

Any photographer can give you the equivalent of that photo you had in high school. That takes zero skill. You want to find a photographer who is really, truly trying to make you look beautiful or handsome - trying to find your best angle. I’ll shoot you from all kinds of angles, climbing on step ladders, and hanging from all over the room to try to find the one that is you. That’s the difference between a standard “school” photographer and a professional.

We’re all nervous about having our pictures taken. How do we prepare?

First of all, bathe! Clean hair is a great place to start. You have no idea how many people show up to a photo shoot looking a little dirty. I’ve used so much dry shampoo.

Second, be well-groomed. If your hands are going to end up in the shot, have your nails done (even if you’re a man, get them trimmed and cleaned). If you’re a woman, consider having your makeup done professionally, especially if you’re unsure about your skill level.

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If you’re a man, make sure that you shave really closely - you’d be surprised how many patches people miss. You don’t necessarily notice it until the photo is blown up to 400x its normal size and you think, “Whoa. What is that furry thing?”

If you don’t take those steps, I have to fix them in Photoshop, which takes more time and costs you more money.

Pick flattering clothing you actually like and feel good in. If you don’t feel good, your whole demeanour changes - you look as uncomfortable as you feel. Don’t put on a top that you bought just because you think you “should.” If you would never wear a white blouse, then don’t wear a white blouse. Wear something that looks like you, something you would wear, which is appropriate to your job.

Make sure your clothes are clean - and ironed! If you’re not great at ironing, take the outfit into a laundromat or dry cleaner. You want to look sharp and well put-together. If you don’t have the outfit you really want - and maybe you can’t afford it - then go buy one, leave the tags on, and return it! (Shhh).

Quick tip: You would be shocked how much cleavage I cover in retouching! Keep on eye on your cleavage when you’re picking your outfit. It’s far more noticeable in your business photos.

I’m super ugly and look terrible in photos. Will you fix my everything?

Everyone thinks that they’re hideous. They think they’re fat and un-photogenic. It’s all untrue; only a very small percentage of the population are actually any of those things. Even if you are most of those things, they can be fixed - you just need to ask your photographer.

Most people are actually quite photogenic. The problem is that we all see ourselves one way and the camera shows us who we really are, and what we really look like. It can be disconcerting. We’re all 25 years old in our heads. We have to keep in mind that other people don’t see the things that we see.

I can fix almost anything. I could turn you into a twelve-year-old if I wanted to. Realistically, I’ll ask you how much you honestly want fixed. If you really hate your double chin, if you want me to take 10 years off, fill in your bald spot - you just have to ask. Be very specific about what retouching and the amount of retouching you want. I’ll fix it just enough that you still look like you.

Gentle retouching takes 5 years and 5 pounds off everyone. If you’re over 40, I just do it automatically as part of the service.

Your photo is your calling card. If you have a photo that doesn’t look like you, or looks like you took it at a party or some other unprofessional location, does that really tell people about who you are and what you do?

Have your photo send this simple message: I am good at my job. I am a competent professional.

All photos in this section courtesy of:

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Jessica Venturi

Jessica is a talented, award-winning fashion and art exhibition photographer who just happens to create amazing portraits of business leaders. Her work has been featured in international magazines such as Forbes, People, and Canadian Living. She’s also been commissioned by well-known corporations such as Royal Bank, Morgan Stanley, Sappho, and Admin Slayer (see what we did there?). Jessica travels the world to work with clients, particularly in Europe. Keep an eye on her Instagram account for updates on her recent work and travels.