In the following video portrait photographer Alex Kilbee (from the YouTube channel The Photographic Eye) takes a look at lessons in portrait photography by one of the most famous living photographers: Annie Leibovitz.
We will be following the different lessons mentioned in the video and bring some of our own input when needed.
Create A Welcoming Space
The first tip or lesson that you can really learn from Leibovitz according to Kilbee is that you need to fall in love with your subject. If you don’t like what you shoot your final image will show it and it is your job as the photographer to create a feeling of intimacy with your subject.
As an example, Kilbee brings Leibovitz’s most iconic image of John Lennon and Yoko Ono and you can see the level of intimacy that they were willing to show in front of Leibovitz’s camera – this is what a photographer should aspire to get from his/her subject.
There are different ways of doing this but talking and more importantly, listening to your subject, finding anything that might be a good conversation starter to break the ice, and go from there as long as you can make a connection – you are on the right path.
Photograph Your Friends
This one might sound controversial to some photographers but Leibovitz suggests that you start by shooting the people who are closest to you (partner, parents, brothers/sisters, and so on). Creating intimacy here is easier and you can experiment more than with a client or a model.
Cut down on the gear
We discuss a lot of gear here on the site but we actually tend to agree with Leibovitz that at least from time to time there is an advantage of working with a very limited set of gear and more specifically lenses. Start with one or two focal lengths and work with them (Leibovitz’s favorite has always been 35mm which is very useful for environmental shots).
Working within limitations can help you make the most of what you have and take you away from constantly rethinking your lens choice. This will also force you to be more creative to overcome the limitations of your gear.
Go with the flow
You might find it surprising but Leibovitz actually speaks in favor of the idea of the portrait being driven by the subject and not the concept. Looking and some of Leibovitz more crazy works this might sound counterintuitive and it is clear that she did have to work on many occasions based on a concept a client was looking for (this is very common in magazines).
However, what Leibovitz means here is that even if you are coming to a shoot with a concept try and see how your subject connects to that concept and be flexible to go with the flow and change it accordingly.
Why does that photo work?
This lesson is based on Leibovitz’s personal history. She started as a photojournalist and what she suggest is that you try and look at the images that you can see in the news all the time (this was more true in the days of physical newspapers and magazines like TIME but you can still do that in the intent age if you know where to look).
Try and figure out why a specific image work. What turns it into an image that you remember, is the lighting, the pose, the expression, or something else, and try and learn from that.
Learn to love light
A lot of great photographers (Leibovitz included) started by studying art and especially the way light affects the subject. Learning how you can use light (including artificial light) to look natural, just like the great painters have done for centuries is the key to really elevating your work.
Kilbee suggests that you start by using natural light and move on to artificial light (either constant or flashes/strobes) only after you feel that you reached a good enough level and want to progress. This is a good tip and even if you do want to work with artificial lights try and start from a simple one-light setup and progress from there.
Revisit old images
Looking at old images is always a good idea. See how you evolved and changed. Maybe there were things that you have done in the past that you would like to re-make with new knowledge, maybe you can spot mistakes and learn from them.
Here is another tip from us. We always suggest shooting in RAW. One of the most amazing things is re-editing an old image using new tools. An image we shoot 10 years ago could look so much better with some of the new tools in Photoshop or Lightroom. Just think how much better you would be able to edit shots that you are taking now with advanced AI tools in 2030.
Seek out inspiration
The final lesson here is actually very important. Try and look beyond photography. If you love a specific style of music or painting or even architecture – anything can be a source of inspiration and you should be able to find creative ways to integrate other things that you find beautiful or interesting in your work regardless if they are from the world of photography or not.
We have covered Leibovitz’s work on LensVid several times in the past and you can see some of her work as well as interviews on the following page.
Iddo Genuth 
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