Guest Interview with Toby Lee, Headshot Photographer

Feb 4, 2024 | Photographer Guest

“Show Notes”

Toby Lee Toby is a headshot photographer in the UK. His business is called Headshot Toby. He has been a Headshot photographer for 7 years. He started out working with actors and those in the entertainment industry. He is now in Lincolnshire working more with businesses.

Toby started out as an actor and went to one of the top acting schools in the country. During his final year at acting school, it was essential to get a professional head shot. His headshot was done by ⁠Robin Savage⁠. Toby felt he really enjoyed the process. He happened to have a DSLR he bought to make films. And he started to use it to take images of his friends on the course. He felt that friends were spending lots of money on headshots. He ended up taking lots of headshots of his friends on his course and got great feedback. Gradually he was spending more and more time on the photographer while nothing was really coming in on the acting front.  Eventually he decided that photography, not acting was the way to go.

This was Toby’s business for about six years. Covid put a stop to this work with actors not work. At that time Toby and her wife made a decision to relocate to Lincoln and Toby transitioned from photographing actors to working with people in business. Toby feels the styles he was using for acting headshots, he is now using in business headshots which means he has quite a unique style.

Marcus and Toby discussed that not that long ago a business headshot was a simple head and shoulder shot with a plain background. While now it has evolved into something much more. When Toby first started to work with businesses, while working with actors, he found it difficult trying to take those dull simple headshots. But now he does much more interesting ones for businesses.

Sam and Toby discuss the fact that people will make snap assumptions about you from your headshot. The headshot also becomes like a logo that people will recognise as they scroll through LinkedIn. Also this images needs to be updated and kept fresh from time to time. There is a balance in using these images between recognition and over exposure. Marcus asks about the process. Toby says it’s all about the interaction with his clients and the photos are almost a bi-product of this. Toby has to build up the client to a point where the client will feel positive about the photos, but also positive enough so they feel able to use them on social media. He finds that on arrival customers tend to come with five minutes of “verbal vomit” where they make lots of negative comments about how they look. Toby lets them get this out but then starts to talk to them and build them up. Toby things it’s important to play for time. So gradually build them up let them get comfy in the space. He also spends more time than he needs faffing with equipment and getting “test shots”. During this time Toby is just building a relationship with them before he starts taking the photos. Then before long Toby can feel the trust has grown enough and he can start. Sam and Marcus said this reminds them of the ⁠episode about listening with Colin D Smith⁠ where he said it was important to listen when people speak and relax into the space. Toby says when his clients leave they say they have had a great experience and are really looking forward to seeing their photographs.

Toby thinks he has lost some work to people using an AI app. But, Toby says he is not really concerned about this as the personal element in the headshot is so important. That building of confidence is so important. But Toby thinks also that AI will help with the post photoshoot work. Toby said lots of photographers in the ⁠APHP⁠ helped him. ⁠Robin Savage⁠, ⁠Nicolas Dawks⁠, ⁠Gareth Bailey⁠ and ⁠Adam Hills⁠. They let Toby come to sessions and assist on shoots, which really taught Toby an huge amount. He found these more inspirational than photographers he found online.

You can find Toby at

“Show Transcription”

Marcus: Well, hello there, listeners. Yes, it’s Marcus and Sam from shoot to the top with another exciting episode for you. Hopefully you’re going to really love this one. We’ve got a fantastic photographer as our guest, so, yeah, Sam, how you doing? You okay?

Sam:  Yeah, very good, Marcus, looking forward to another great show and good to be with you. Marcus: Thank you. Ok, so we’ve got Toby Lee. Toby is a headshot photographer based in the UK. I’m looking at me on the screen now and he’s nodding, producing. He’s got a lovely smile, but you can’t see that, of course. So let’s go over the Toby so he can tell you a little bit more about himself.

Toby: Yeah, thanks very much. Thanks for having me today. Yeah, I think you sort of summed it up. So my business called Headshot Toby, and I’ve been a headshot photographer now for seven to eight years. And, yeah, it’s been an interesting journey, sort of transitioning my work started out working with actors and performers in the entertainment industry, and now I’m based in Lincolnshire, which is where I grew up, and it’s now sort of transitioned more towards working with businesses and professionals.

Sam:  Cool. So do you want to take us back to the beginning, Toby? Because my understanding is you didn’t start out as a photographer.

Toby:  No, absolutely. Like, a lot of photographers didn’t necessarily start out in photography. I actually trained to be an actor, so I was fortunate enough to go to one of the top drama schools in the country. Went down to London at the age of 18 and, yeah, was looking to pursue a career as a professional actor. And going into your final year, when you start inviting agents and things to come see your showcases and the dream starts looking a little bit more realistic, you have to get a headshot photo. And that was my first sort of exposure to what a headshot is and sort of trying to understand why you sort of need one, particularly in that industry, from a sort of casting point of know it’s your shot window. And I remember the experience of working with my photographer. He was a guy called Robin Savage, and if you get a chance to look at his work, really lovely portrait headshots. And, yeah, just had a real connection with him and the whole process of it, there was just something about it that I really enjoyed. And I had a camera that I was thinking trying to make my own work as an actor. I could make some short films. So I had a cheap DSLR that I was trying to do some films on and I sort of started taking photos of my acting colleagues and a lot of them would spend an incredible amount of money. What felt like that at the time and the stage you’re at in your career, spending three, 4,500 pounds on a headshot session to then majority of them sign with an agent and then be told, headshots don’t quite represent you how we want to represent you. So can you just grab a friend to take some pictures in the meantime so you can afford to get some new ones? So in walks me, guy with a camera, and I started taking photos for a lot of my colleagues in my year at drama. You know, started getting really good feedback from their agents. And a lot of it was just sort of mimicking what my headshot session had been with Robin, to an extent. Find a tunnel in north London somewhere and find some nice lighting and that. And then it sort of just built from there, really to the point where I had a decision to make. I was investing any money that I sort of got from charging a little bit here and there to buying more equipment, started bringing speed lights into it for hair lights, rim lights, all those kind of things. And acting was just incredibly quiet. It was that cliche of just waiting for the agent to call and he could call at any point and you’re expected to drop everything and be there at that audition. And so it got to a point where I’m sort of tiptoeing around this sort of potential business venture here where there’s clearly a lot of interest. I’m getting some great feedback and response. And so I went, sort of dived into that pool and went for it. And business grew all the way up to the point of COVID which would be about a four or five year period. Yeah, I was shooting with actors that were working regularly on television and film work and theater work and making really nice connections with agents and things. That’s sort of how the acting side of it went. And that was the business for, like I say, a good four, five, even six years. And then obviously, Covid, like most people’s work, put a bit of a stop on everything. Not being able to work in that closer proximity. Actors weren’t being able to work at all anyway. So the need for a headshot at that point sort of came to a bit of a standstill as well. And that was when my wife and I, who, she’s from Yorkshire and I’m from Lincolnshire, we sort of made that know we don’t want to be in London forever. Anyway. What does that look like if we were to now use this hiatus as a point to move? So we ended up relocating to Lincoln, and now my work has kind of transitioned into working with business professionals, and I think hopefully offering something that’s a little bit different style wise, taking all that sort of inspiration that I’d sort of learned and looks and styles that I’d developed working with actors, where the headshot needs to be a little bit more sort of cinematic or a little bit more editorial at times, there’s a lot of different requirements and also getting very different sides out of people. I think that’s now a little bit of a USP for me when working with sort of business individuals that they probably think they’re turning up for that kind of typical corporate shot. But actually, we’re offering something a little bit different now, not only in the aesthetic of the photo, but also how I work with the individual.

Marcus: Okay, so it’s interesting, your journey you’ve got here that you started off doing acting head all of a sudden, dare I say, post Peter Hurley business headshots in this country seem to be the new headshot. Is that how you’ve seen it change, or do you think business headshots have been there from the beginning and I’ve just missed out on?

Toby: No,  There’s, I think. I think a headshot before, in a business sense, was very much that kind of white background, get something professional looking on LinkedIn and that awful business card, and that was probably the main use for it. Whereas now, I think because we’re so sort of visually versatile, we’ve had to sort of up the standards of what’s going to get people’s attention. I think that’s probably why it’s crossed over into kind of being more of an essential tool. It’s certainly something that when I started out working with actors and tried to find a little bit of corporate work, I sort of struggled for my personal motivation of it because I was thinking, well, I don’t really want to offer what they’re expecting in terms of a simple kind of white background headshot or whatever that might be, and didn’t really see much potential. Whereas now, having been through that journey of working with actors and sort of, I’ve grown to learn that actually all those essential tools or essential reasons that an actor needs that tool do actually apply to anybody within their career. That’s kind of like a lot of the advice that I sort of try and share now, further your own career and you’re working with an employer, your photo, your headshot is still your shop window. If you invest in that, it shows you’ve invested in your own worth and value, and that’s going to accompany whatever posts you’re posting on LinkedIn and so on. And we start building this bigger picture that all starts from the root of that photo. But if that’s not there, if we’re using a kind of holiday selfie, which a lot of people do on LinkedIn, suddenly it becomes far too personable. We don’t quite read your content with the same level of authority or professionalism or whatever. We might want to put a label on that. But yeah, no, that is an interesting point. I definitely think it has grown, and I think that kind of demand for something that’s maybe a little bit more sort of editorial or would suit being in kind of magazines or looking like you may have been part of some sort of published article or something like that tends to just give us that little bit more time when we scroll a little bit more attention when we stop and look.

Sam: Yeah, I guess it’s almost like that when you talk about social media or you’re looking at websites, you’ve got moments to grab people’s attention and you’ve got moments in which they make very, very fast judgments. And, yeah, one of those will be your headshot, won’t it? They’ll instant look and they will make some assumptions about who you are, where have you come from, what your authority is in millisecond? And that’s got to be just right.

Toby: Yeah, absolutely. With it being your sort of shop window, it’s the bit you recognize. So as you’re scrolling, say, let’s keep LinkedIn as an example, because that’s probably where majority of my clients are nowadays. We’re wanting them to build familiarity with that photo. So they’ve seen your photo before, they’ve read your content, and they’ve engaged with it. So almost like a logo now, whenever they’re scrolling and they see that slightly green background or whatever it is that your photo has got, that’s going to make it have that little bit of edge that they then instinctively stop again because they’ve attached it last time. This was a good thing to do.

Sam:  Yeah, that’s interesting. Yeah. I’d never thought of it like a logo. Almost like people just spot it and know this is something interesting.

Toby: Yeah, exactly. And putting that back into kind of actor context, you kind of want to keep consistency with your photos so that you’re recognizable. But at the same time, it’s also trying to make sure you’re one up to date because it really needs to represent you when you walk into that casting room. Just like whenever you walk into any meeting your business headshot needs to, then it’s also trying to renew that brand and keep that brand up to date so that we don’t actually get to the point where we start scrolling past because we’re oversensitized to seeing that photo now. So we want to keep it fresh. So, yeah, there’s a lot of kind of layers to it.

Marcus: Tell me, Toby, talk to me about the process involved in this. Not so much the technicalities, but how you work with your clients and how you make your photographs or your portraits stand out from other people’s.

Toby: Yeah. Okay. So I think one of the elements that I’ve learned most is that my session now has become about the interaction. The fact you’re going to get a photo with it almost becomes a bit of a side product. And that’s mainly because the transition of working with actors who are majority of the time confident, erring on the side of ego, but positive ego and that kind of front. But actually, it is very much a mask that to get a really authentic photo, you almost have to break them down a little bit.

Sam:  Okay.

Toby: And now working with sort of, I call them normal people, it’s a case of. And I don’t mean that with any disrespect. I mean people that would never go in front of the camera unless they had to. And this is usually the position my clients are in. It’s a case of. Right, I’ve got to build you up to a position where not only are you going to view these photos of yourself and have a positive response, you need to leave this session in a place where you’re ready to actually use them and share them, because otherwise, this has all been a waste of time for you and your investment and sort of learning that in sort of the last year or two has really changed my sort of approach. Now a lot of clients will turn up with the typical anxieties and I call it sort of verbal vomit. The first 5 minutes when they come in, oh, God, I hate my smile. I don’t have to smile today, do I? Are you’re not going to get my chins, are you? All these things that come out, and if I had a pound for every time one of those lines came up, I won’t be doing this, I’ll be somewhere else. But it’s trying to let them have that moment, have that space, get that anxious energy out so that then I can start to work with them and acknowledge a couple of the things that they’ve said, start talking about and say, well, actually, I’ve got a couple of ideas as to why you might not like your smile and so on, as to why you feel uncomfortable in this situation. At the end of the day, it is a thing to be doing. I’m a stranger, you’ve only just met. You’re sitting in front of me to capture photos that are going to represent you as best they can in a completely unnatural setting. You’ve got lights around you. I’m holding clipping bits of blackboard either side of you to flag it and all these things. And there’s also that element of that when somebody comes into the studio, having seen your work and booked you upon that, they don’t really understand the setting, what it’s going to look like when you actually sit in it and sit in front of the camera and trying to visualize the end product of what they might look like in that photo seems like a real far distant challenge to overcome.

Marcus:  How do you overcome that challenge then? Toby?

Toby: So a lot of it is playing for time. So I’ll show them the sort of dressing area, let them hang their clothes up, let them have a bit of time to sort their hair. We’ll talk through outfits over a cup of tea and things like that, and how I’ll pair that up with different backgrounds and looks. And then when I get them in the chair, I say, buy a bit of time because I’ll probably faff around moving lights and things far more than I need to because I know exactly how I’m going to shoot and what I’m looking for in that shot. But if my focus is on the lights and not on you, the subject, you’re not going to be worrying about me. I’m not pointing the camera at you yet? Because I’m taking test shots. I say gesturing, inverted quotations there. I’m taking test shots. You just sit there, you just chill. Let’s keep talking about what you’ve got on for the rest of the day, or where do you think you’re going to use these photos and just get them talking? And there’s a real point where it sort of clicks and it usually only takes a couple of minutes where they’ll share something quite personal or something that you maybe didn’t quite expect. But it’s that little in that just lets you know that, okay, the level of trust is there now that we can start snapping and almost transition into taking these photos now and stop faffing with test shots and moving bits around. And actually, before they know it, we’ve sort of finished that first look and we’ve directed through the different sides and chin this way. Now just turn this way in the chair and look back to me and so on. And we’re onto the next outfit. And from there they’re sort of fairly comfortable.

Sam: Okay, that’s really interesting. It takes us back to the episode Marcus. We recorded a little while ago with the listening guy, and he was talking.

Marcus: Oh, man. I was thinking,

Sam:  Because he was talking all about that, making time just to listen, which is basically exactly what you’re saying, just stop. Let them get all that panic out and just listen and let them relax into the space.

Toby: Yeah, that’s it. Because I think if you’re confident in what you offer and you know you’re going to get that regardless, you know you’re going to capture what you need to. You can always give as much time as the subject needs. I don’t think there’s anything worse than going in front of the camera with a photographer and you feel a bit rushed off your feet and then the session is over and you’re thinking, well, I don’t know if I’m going to like these photos when I get, when the anxiety carries on, when my clients leave, if what they tell me is true, they’re leaving incredibly excited to see their photos. They’ve had a lovely experience regardless. So I’m thinking, well, that’s going to help how they view their photos and I’m keen and confident that they’re going to be using them and sharing them as much as possible, which obviously, at the end of the day, if they’re doing that, it’s good for them. And also it’s very positive for me.

Marcus: Yeah. We had a guest on a forthcoming show with Martin Hobby who’s in the same market, same game as you. I’m sure you know him. Headshot photography. And we talked in the pre-show, we didn’t manage to cover it in the main show. We talked about AI and how that might be changing the impact. And I welcome this opportunity with you, Toby, to just get your thoughts on the way it might encroach on headshot photography.

Toby:  Yeah, absolutely. I’ve certainly had the inquiry that I’ve probably lost down to them using an app. In the end, it’s only happened on probably one or two occasions that they’ve inquired. I’ve tried to follow up, and then a couple of weeks later they’ve said, I just need it last minute. So I paid $20 and got all these different AI ones. I think from that point of view, in terms of losing any headshot clients to AI apps, I’m not that concerned, because, like I say, that personal element is so huge to the process that I think that will always be needed. And in terms of how it sets you up to look confident and to appear professional, and approachable, all those things that you need to do, you can’t always get in a selfie or someone taking a picture of you in front of a wall so you can upload it to the app. So I don’t have too many concerns about that. But then I think there’s a huge world of excitement that it is going to help our processes and our workflows down the line. I think I’ve tried a few different apps for retouching and things like that. I still always go back to the. The actions that I’ve already got in Photoshop, because for me, it just feels far more just believable. A lot of them for sort of retouching, I still find, like, we lose bits of skin texture or it’s just not quite reading how it should. So, yeah, at the moment I don’t use it too much, but, yeah, I think there’s some exciting things to.

Sam: You see it quite positive. You see, it could probably help with just that. What photographers spend a huge amount of time doing is just sitting at the laptop, and it could help with that and cut time. But in terms of the photography process itself, it’s not a human to human interaction, is it? So it’s just not the same experience.

Toby:  I think we’ll always place value on that. And as long as some people are always getting professional photos from a professional photographer, other people are going to look to that and it’s going to be something that might even become more valuable and more premium, but it’s something that they know they should do. So whether they then turn to the cheaper option, it’s always going to be seen as. I took a bit of a compromise here and went with the AI version or whatever you could say. It enables, say, massive corporate businesses to photograph all their stuff in house without having to get a photographer in, without any of the editing costs, without any fees other than what it cost them for the app to do, say, 500 employees and 500 photos. But you’re not brand recognition. It’s probably not always going to have consistency across the board, and there’s going to be sort of teething issues with it, I imagine. I haven’t actually used it.

Sam: And in some ways, selecting out, to be honest, those customers that would prefer to save some money can often, as a business, make your life easier, can’t it? Those that are really pushing the price down, those that really want to pay as little as possible, are usually those that demand the most, are the most awkward. And in some ways, if it can filter those out for you, that’s probably a good thing.

Toby: Absolutely, yeah. I wouldn’t hesitate. If somebody came to me and said, I’ve only got a budget of 50 quid, then that’s fine, I’m not going to be too much help for you, but I wouldn’t endorse it, but I wouldn’t say, don’t do it, go and do it, and that will serve you for a couple of years till you’re ready for that investment in you and your business. There’s no sort of judgment cast on it. But like you say, it does rule out certain inquiries, which is also why I list my packages on my website. I know it’s always a question for photographers whether you do or you don’t, but because I just offer sort of studio headshot sessions, it’s there, it’s clear to see and you can decide for yourself, sort of thing.

Sam: Cool. That’s amazing. And I think so. Sorry, go on, Marcus. We do need to wrap up as well, but gone.

Marcus: Yeah, we’re going to. I just want to get this one in. Thank you. Thank you, Sam. Yeah. We’ve looked at the future and I was just going to ask you, Toby, looking to the past, any particular references, photographs that you particularly are drawn to?

Toby: Do you know what? A lot of my sort of. I’ll call it training, because it was very much mentorship, were the main guys involved with the association of Professional Headshot Photographers, the APHP. So that was set up. They’re all actor casting headshot photographers. And it was set up to sort of maintain the standard of that photo with a lot of other photographers starting to offer to actors, but not necessarily having sort of that expert insight into what the industry requires. So there were certainly photographers like. Yeah, Robin Savage, Nicholas stalks and Gareth Bailey of Franklin and Bailey, those three guys, and Adam Hill’s photography as well. Those four, they let me come along to sessions, they let me assist them on shoots and things like that and just be a fly on the wall and just seeing the way they work, both technical and with the talent, that was huge. And I’d say they were probably more inspiration to me and motivation to go and try stuff than sort of anyone I sort of found online or on YouTube or sort of other photographers.

Sam: Cool. And then we’ll put links for all of those in the show notes so people can go away and see their sweet.

Toby: Yeah, yeah. Absolutely

Sam: Brilliant. Well, it’s been really interesting speaking to you, Toby, and. Yeah, really interesting. Right back to beginning, the fact your kind of story is on its head. We were saying before we started, we were chatting that most photographers, you go to their website and it says, I got a camera from my dad when I was nine and I’ve loved it ever since. Well, yours is completely inverse of that, isn’t? It’s like I wanted to be an actor and I kind of fell into it accidentally.

Toby:  Yeah, absolutely. And I love it because people say, do you have any regrets about acting? Would you ever take it up again? And it’s like, the answer is pretty firm. No, because I wouldn’t be doing what I’m doing now. If I hadn’t gone down that route of trying to be an actor, I wouldn’t know what a headshot photo was.

Sam:  Brilliant. All right, well, thank you so much for being with us on the show. Our listeners have learnt so much and it’s been really interesting. So thanks for being with us.

Toby:  Thanks very much for having me.

Sam: Pleasure, Marcus. I will see you next week.

Marcus: See you next week, . All right, have a good one. Take care.