Interview with Professional Headshot Photographer, Aliyah Dastour

When you’re the face of your brand your headshots can make or break your website. Today I’m sitting down with my go-to headshot gal as we walk through the most common questions asked when it comes to getting headshots for your website.

Aliyah Dastour is my favorite headshot photographer and owner of Alimond Studio in Leesburg, Virginia. In this interview, she shares priceless tidbits about how to get the best headshots for your new website.

Before you head to your next photo shoot, take a listen to our conversation below:

Don’t have time to watch the full video? Below I’ve summarized some of the best pieces of our conversation while highlighting the key questions and answers.

  1. What’s the difference between corporate headshots and headshots for your website?
  2. What should I wear for my photoshoot?
  3. Should I get my hair and makeup professionally done?
  4. Where should I take my photos? Is indoors or outdoors better?
  5. How do I prepare for the session with my photographer?
  6. How many photos should I purchase?
  7. What would be your advice to those who are uncomfortable with their photo being front and center on their website?
  8. Closing comments from Aliyah.

What’s the difference between corporate headshots and headshots for your website?

When coming from corporate, clients tend to think of the term headshot as that standard gray background, cropped portrait orientation, arms folded… but I know headshots are different when it comes to websites. So what is the difference between headshots for your website versus that “standard” corporate headshot?

Aliyah’s Answer: 

A lot of people come to me in that same boat. They’re corporate and they want to look good and they don’t want to blend in, but they have to blend in enough to where people don’t discredit them. So I think that’s the biggest thing. 

If you still need to attract corporate people, you have to be able to still fit in with them and make sure you’re not alienating them. 

You don’t want to do some creative photos and then people see that and they’re like, “I don’t vibe with this person. It’s too different from what I was expecting by getting into a professional relationship with this person.”

So there’s a balance, to answer your question. 

There needs to be something where you go outside of the box and not just do the head and shoulders looking straight at the camera, gray background, etc. There’s no dimension with that.

You can create some really creative photos, even if you have to stay within that gray. A designer can even extend that background out a bit make it look more personal on a website. 

So first of all, you’ll want to know what your goals are for your website (and thus your photos). Then, secondly get a good mix of your personality in your photos, whether it’s on the standard gray background or outdoors. A really good set of photos, not just headshots, they need to speak to your viewer.

What should someone wear to their photoshoot session?

Click here to view some of my favorite headshots + outfit inspiration.

Aliyah’s Answer:

Once again, it always goes to your goals because there’s no one size fits all. So talk to your photographer and communicate with them.

Your photographer should be asking questions like, “What’s the point of these photos? Who are you trying to speak to? Who are you trying to look like in terms of who are you trying to fit in with? Are you trying to stand out?”

Because from there that’s what’s going to determine what you should wear. 

So if I had a client come to me and they were a real estate agent, I would then say, “Okay, how do you want your clients to think of you? How do you want them to feel when they see your photos?” And if they reply with, “I want them to know that I’m selling the million-dollar, multi-million dollar houses,” then they need to make sure that’s how they’re putting themselves out there. So it speaks to that clientele.

 Versus somebody who’s like, “Hey, I’m a dog walker and I’m trying to start speaking in front of these conferences for dog-specific industries.” I’m not going to have them show up in a nicely fitted suit, photographing at a five-star luxury hotel because that’s not going to fit the brand.

So in terms of clothing and outfits and what you should wear, number one, never just have one outfit. Always bring multiple outfits. 

Then talk to your photographer about your goals, but make sure that the outfit feels like you. Ask yourself, if you’re meeting your ideal client for the first time, what would you wear? That’s the type of stuff that you want to bring in. 

There are some standard things to kind of think of, too:

  • Stay away from crazy patterns.
  • Horizontal stripes make you feel a little wider.
  • Avoid having your hair pulled back.
  • Keeping your outfits more neutral allows for greater flexibility in your website design and where you use your photos.

Side note: You also don’t have to wear a blazer to be professional. There are so many other ways you can show up as a professional. Now, if you are the blazer suit type of person, do it, wear it. If that’s who you are and that’s how you show up and you feel confident that way, do it. 

I’ve seen a lot of people who would never wear that outfit feel like they have to put on the blazer in order to be a professional. That is just not true. There are many other ways that you can look professional and that is how you carry yourself in the photos.

Little tweaks, such as having your chest up, shoulders back, kind of looking over to the side, chin slightly tilted. It feels more like, “Okay, this person is grabbing me in. They know what they’re doing. They know what they’re talking about.” 

There are so many other ways to push professionalism across a photo versus just putting that jacket on and more than likely that jacket doesn’t fit you well. It’s got weird creases in the arms and you feel uncomfortable and it says it all over your face.

Do you recommend clients get their hair and makeup professionally done before their photoshoot?

Aliyah’s Answer:

I would say get it professionally done by the person that already works with you. Don’t go for somebody that’s new. I do have somebody in my studio as an option for people who don’t ever get their hair and makeup styled so that they don’t have to stress out over it.

But I will say people do their makeup in a specific way and they style the hair in a specific way. So if somebody is doing that for your photos and they don’t get it right, whenever you look at your photos, you’ll be like, “That’s not me. I don’t look like that and now I have to put my photos out there.” You’re going to hesitate to put yourself out there and sharing the website and all that stuff.

Work with the person you already work with if you have somebody. If not, bring in a photo of what you normally look like or bring in a photo of what you look like with your normal hair and makeup done the way you like to see yourself, as well as maybe if you wanted to jazz it up a bit. 

Be like, “But I like the way Angelina Jolie looks in this photo. So I want to have a mix between how I normally do it and how she normally does it.”

How do you determine where to take your photos? Do you recommend in a studio or outdoors?

Aliyah’s Answer:

I always go for a combination of both, but let me give you my justification for why. 

So a lot of times people will come in and they’re like, “I just want indoor photos,” because of something they’ve read or something they saw or something they were told. But then we go outdoors, it just captures a different side of them and it tends to be more of a lifestyle feel.

For anybody that’s doing any marketing or social media or developing a new website, they’re so grateful to have those photos to show that different side of them and vice versa. 

Others are like, “I just want environmental outdoor photos” and I’ll end up capturing them indoors as well and they’re like, “Wow, that’s exactly what I wanted.” It’s a different feel to the image.

It’s not that one is necessarily better than the other. It just captures another side to their personality.

At the end of the day, that’s the whole point of headshots, portraits, photos to be able to see a photo of somebody and say, “I feel like I know them just a little bit better after looking at this photo.” 

You want to end up with multiple photos that say different things.

I used to shoot for a magazine and the space around the photo was the biggest thing that I needed to be able to do. Have as much white space, negative space to the side of the photo. Even if we were going outdoors to shoot make sure that you have photos where we’ve got some out-of-focus blur within the photo.

A simple photography technique that every professional photographer is going to know how to do, separating you from the background a little bit. So you’re the main focus and everything else is out of focus. That way you can still create all the elements that you need for the website design without seeing these super in focus chairs or stairs or trees.

Is there anything else that clients need to do in order to prepare for a session with their photographer?

Aliyah’s Answer:

This guide helps people prepare for their session at my studio.

I’m big about thinking about the strategy behind the photos.

You want to make sure your photographer has a game plan of exactly what they’re supposed to be capturing. A lot of it comes down to personality and emotion because your photos should be standing out in some way.

I just recently photographed somebody who was a holistic physician and her whole brand, she’s very serious. She’s very well respected in our area. People love her, but her expressions, it’s a very solemn, very serious, calming nature about her. So if I didn’t know that, and we still got some smiling photos, but if I didn’t know that and I try to get her to smile all the time in her photos, she would have been really uncomfortable because that’s not who she is. Plus, she would have been left with a whole bunch of photos that she would look at and be like, “These are pretty, but they’re not me. This isn’t my brand and what I’m trying to represent within my website and all of my marketing materials.”

The biggest piece is your strategy behind why you’re getting these photos created. Then the emotion and the feelings you want your audience to have when they look at your photo.

As an entrepreneur when they’re the face of their brand, how many photos do you typically recommend they purchase?

My dream scenario is for a client to send me 25-50 photos that I can just pick from as I build their site. So many clients ask me how many photos to get and I always tell them to let the photographer take as many as possible. I recommend they get as much as you can within their budget.

Aliyah’s Answer:

So to go back a little bit, normally when they’re getting their website done, they’re creating more than just their website. They also need social media content. To have photos for multiple blogs posts. Or are going to be featured in different places or at least that’s their intention and goal.

As their photographer and I want them to get all these amazing photos. But I always tell them, “If you love the photo, get it because you’re going to be able to put it to use.” 

You might only use 10 of those images. 5 to 10 of those images across your website, but then they’re going to be able to also use the other images on their social media posts. If they’re going to do YouTube videos on the thumbnail. It could be something where they’re actually pointing or smiling or doing something and then the actual title is being put within the photo as well in that negative space that your photographer captured.

So think not just short-term when you’re creating your photos. Think long term. 

Think, “Okay, if I’m going to use these for the next 6 months or for the next 12 months or 18 months, let me try to get all the different looks that I want to be able to capture and use for all of my marketing content.”

What would you say to those who are uncomfortable with their photo being all over their website?

Aliyah’s Answer:

In my heart, I’m obsessed with everything marketing. I’m just obsessed with it. So for me, I understand why it’s so important to put your face everywhere. If you feel super uncomfortable with seeing your face everywhere, more than likely, it’s an underlying issue of not wanting to be out there and not wanting to feel like you’re too self-promotional. I understand that. I can understand why.

Obviously, there has to be a mix. 

People need to know when somebody is coming to your website, they want to know the value that you’re going to bring them. But they also want to know you. 

You’re selling your brand, your personal brand. You’re selling yourself, your image, the value that you’re going to bring them and what better way to do that is through you? 

I mean, think about it. People pay millions of dollars to have one of these huge celebrities selling their products because they understand the value of their face being the one on the website or on the can or on the marketing materials to sell their product.

That type of value is what you’re creating when you choose yourself to sell your products or your services. 

So if that is a concern, maybe put together some self-hype why this is so important that you are selling your business. Because I think a lot of it just comes down to what we were told as a kid or as a teenager.

I have a client and she just reached out to me and she was like, “Hey Aliyah. We’ve got to be careful about saying that I’m the number one agent.” And I’m like, “But you were voted 10 times as the number one agent.” Because somebody posted on her social media, “Number one agent? Hmm … Cool.” Something like that.

So it just comes down to your self-worth and other people saying something and perhaps you’re afraid like, “Oh, I don’t want people to think I think I’m too much or that I’m bigger or better than I am.”

So just own it. You’re investing your money and creating a beautiful website. You’re investing your money in creating beautiful photos. Be your number one fan. 

Be that mom or dad that’s like, “You can do it. You can do anything. Put yourself out there. Be proud.” If you’re a mom and you get your kid’s pictures from school, that stuff is plastered on a fridge. It’s in the frame. You’re proud. Right? Do that for yourself.

Is there anything that you would want to add to this conversation?

Aliyah’s Answer:

I think just touching on that last question that you said. That was such a good question. 

Know that you’re good enough to put yourself out there. Choose yourself. 

People are like, “Oh, I want to use a stock image,” or, “I want to put my clients on there.” There’s a place for your clients on your website and your designer will be the one to tell them exactly where to put those testimonials and all that stuff. But, as you said, when they come to your website, especially if it’s,, they want to know who they’re working with. They want to feel comfortable.

You are giving them permission to trust you for them to work with you. You need to say, “Yes, I’m good enough. I’m confident enough that you can trust me to work with you.” 

And to tie it into your website design. I think having a great set of headshots is amazing but then to be able to work with a professional web designer who can create an experience for your audience is important. You want to work with somebody who knows how to truly create those emotions and feelings for your visitors.

All of your websites, I’m obsessed with because when I go on there, I feel like I know the person. I feel connected to them in some way from how you’ve been able to integrate the photos, to the copy, to the choice of the font. There are so many different pieces to create an actual experience. And I think all of that is crucial in order to get your prospects or your audience to click that “Work with Me” button.

Connect with Aliyah:

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 with interior design and service-led businesses elevating their digital homes with poise and personality.

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