I don't feel particularly qualified to give advice on this subject. Not only because I am not that experienced, nor have I judged competitions, nor do I feel my images are the best taken in the UK in the last 5 years. It's also because it's a completely subjective process on which there are few consistent and worthwhile tips to offer which would make a difference.
What I'm recording here is my (conscious) thought process in shortlisting entries and why I personally choose to enter the few photography competitions I do enter. Most photographers entering LPOTY will have to choose from a large library of recent images (in the last 5 years) and reduce that down to a few entries (1-25). Here's a suggestion as to how to go about it, we will see if it bears any fruit this year or if it's a load of all ramblings.......
I generally start my shortlisting by creating a new collection in Lightroom, setting it as the target collection (right click) and then reviewing my photos at their thumbnail size. As I scroll through I can highlight the images that catch my eye, press B on the keyboard and it starts to fill the collection with those images which might just appeal to a judge who has only a few seconds to view your entries. I think the thumbnail test is quite a powerful tool for competitions as it comes close to the kind of process a judge (at the first round of shortlisting) might be using. They don't have time to understand the emotional element of an image or the subtle compositional decisions you may have made. They are probably looking for the attention grabbers, those with powerful compositions, colours, tones, shapes, events etc.
A lot of landscape photographers take pride in forming their own vision and style over a period of time. I think to some extent you have to ignore this mentality when entering competitions and not submit say 25 images all of a similar subject matter, tonality or atmosphere. If you do take that approach the risk is the judges this year aren't in tune with your vision and even in round 1 you may miss out. After all you can't expect every judge to uphold the same views on what makes a great image as you do yourself. That doesn't however mean you should dismiss those images you feel are fully in tune with your own vision of the landscape and reflect your style of photography. I think it's finding a balance between the eye catching thumbnail images and those you already had in the back of your mind to enter as they are your own most loved photographs. I think my Arts Tower image ticked this box for me, I had an attachment to the image which meant I always wanted to enter it not only or it's subject but because it felt like 'my style & vision' with the subdued blues & greys and simplicity found in the urban environment. It's probably rare for those images you really feel connected to to achieve competition success, that doesn't however make them any less of a great image. After all you should be taking and creating the photographs you want to see and hopefully that connects with a wider audience at the right time.
A lot of the points here apply not just to entering competitions but photography in general, this point in particular holds true in that respect. Without diverting myself onto a big discussion into this matter, think about a balance of entries that aren't all like something the judges will have seen before. An example might be black and white urban architectural images which I image might dominate the urban view category 1st round entries. You will have to take a really creative photograph of a building or city scene in that general style for it to stand out. I'd say a similar example might be the typical sunrise or sunset images within certain locations. If your image of say the Great Ridge from Mam Tor is entered it will be competing with at least a few other images from that same location and perhaps in a similar style. What is it then that makes the judges pick your image ? For me personally to submit an image of an unknown piece of the natural world and have that shortlisted would be more rewarding than having 'the best' photo of the Great Ridge that year.
Finally with any competition you have to consider the end game, what is the organiser looking for and what will the images be used for. To some extent this point contradicts point 3 as I feel for the LPOTY competition some of the awards are actually looking for more iconic images of the British landscape which means often the well known locations. The Countryside if Great award isn't going to be awarded to a more intimate monochrome image of vegetation say, it needs to be an appealing photograph to sell the British Countryside. In the year 2015 there aren't many parts of the British Isles which haven't been photographed so those iconic landscapes are often the the most popular not due to people following the crowd but because they are genuinely the most dramatic, impressive or photogenic of landscapes. Glen Coe for example is an especially beautiful, daunting and dramatic landscape easily accessible so it will always make up a good number of entries into the competition and rightly so. Again it's finding a balance in your entries between the types of images to submit for your own artistic purposes and those that fit the aims of the competition.
So in summary, four points I'm thinking of along the way to entering some images. I'll probably enter 25 as I'll feel then like I've achieved some kind of balance between each of the four points above. I'll be hoping that each of them does well for it's own reason either due to the place getting recognition, my own style being recognised or it's appeal to the masses. They are all valid reasons to enter the images and yet if they are successful or not they will all still hold that same meaning and purpose to me and hopefully others, just not in this particular competition.
Good luck to anyone entering this year.
Dan is a landscape & nature photographer from Sheffield in the UK.
Catch my latest travels on Instagram here.